History • Timeline • Legacy

HISTORY

The story of the Concrete Classic — from a cold round in Effingham to the most competitive trip in golf.
Nine trips. One shared history.

The scores tell you who won.
The stories tell you why it mattered.

A cold round in Effingham became a trip to Wisconsin. Eight players became sixteen. New games, friendships, comebacks, and a trophy bearing Bryan Willis’s name gave the Concrete Classic its identity. These are the chapters the group built together.

Tom Seaborg holding a champion gift commemorating his inaugural trip win
Chapter 1

The Rise of Tom

2018
ChampionTom Seaborg
Points115
The chapter8 players · The inaugural trip

Story

Austin Willis at breakfast with pancakes
One of the few surviving photos from the first year: Austin at breakfast, part of the early-rising breakfast crew that formed almost immediately.

The Concrete Classic began on the drive home from one of the worst rounds Jake Willis and Andy Terry ever played. On February 18, 2018, they headed south looking for golf. Champaign still had snow on the ground, so they kept going until they ended up in Effingham. The weather was cold, the golf was terrible, and the whole day was miserable. Somewhere on the way back, the frustration turned into something useful. Jake and Andy started outlining a golf trip — not just a place to go, but a weekend built around games, points, and competition.

A couple weeks later, that idea found a home. At a golf show, Andy met the head of golf at Fox Hills in Mishicot, Wisconsin and got a Memorial Day weekend deal put together. That was the opening. The original field became Jake Willis, Andy Terry, Bryan Willis, Austin Willis, Dean Johnson, Tom Seaborg, Troy Seaborg, and Gabe Friend. From the beginning, the trip revolved around team games, and from the beginning, total points determined the champion.

Fox Hills fit almost immediately. The property had 45 holes and the group had its own villa, which made it easy to stay together and build the weekend around more than just tee times. The first year also introduced one of the trip’s smaller but lasting traditions: the early morning breakfast crew. Austin, Andy, Bryan, and Dean became the guys who got up and went out early while the rest of the house moved slower. That became part of the rhythm of the trip almost as quickly as the golf itself.

Tournament Breakdown

Jake Willis sitting on the green after a close approach shot
One of the few true on-course photos from the inaugural year, capturing the kind of personality that was already starting to define the trip.

Several of the formats that still define the Concrete Classic were there from the start. ABC-D was played in the inaugural year and remains a staple today. Vegas was also part of the original lineup. In that format, the lower score became the first digit and the higher score became the second, so a four and a five turned into 45. Vegas was eventually retired and replaced by the current two-man aggregate final round format, but in 2018 it was still part of the core schedule.

The group also played a single-elimination two-man scramble bracket known as 9x9. Jake and Dean won that event, and the trip also marked the beginning of a friendship between them that grew far beyond golf. The 9x9 four-man portion was won by Austin, Bryan, Tom, and Troy at two under. A separate four-man scramble was won by Austin, Bryan, Gabe, and Troy at three under. These were distinct events in the inaugural schedule.

The final round in 2018 was true alternate shot. That format no longer decides the overall champion, but it still lives on inside Ryder Cup play. Even in the first year, the group already had the right instinct: rotate formats, keep everybody invested, and let the total body of work decide who came out on top.

Results

  • Champion: Tom Seaborg — 115 points
  • ABC-D Winners: Andy Terry, Gabe Friend, Tom Seaborg, Troy Seaborg
  • Vegas Winners: Jake Willis and Gabe Friend
  • 9x9 Winners: Jake Willis and Dean Johnson
  • 4-Man Scramble Winners: Austin Willis, Bryan Willis, Gabe Friend, Troy Seaborg (-3)
  • Final Round: Andy Terry and Tom Seaborg — +23 in true alternate shot
Tom finished the first trip as champion, and his win was later commemorated during the following year’s trip — the image now used to open this chapter.

Defining Moments

The first great clubhouse story came at dinner. Several guys ordered the prime rib special. Tom took the queen cut because he thought the king portion would be a waste. Andy and Gabe ordered what they thought was a pound of wings. What arrived looked closer to six or seven total wings. By the time the clubhouse tried to make it right, everybody else had already eaten. The two guys who thought they had found the best order on the menu ended up eating last, and Andy has been hearing about it ever since.

On the course, Andy and Tom took control of the final round. At one point Jake brought both groups together and played eight wide for a good stretch of the back nine in an attempt to slow them down and get in their heads. It did not work. The shot that lived on came when Tom hit his third from the 10th fairway onto the 18th green, and he and Andy two-putted for par and the win.

The closing moment of the trip became part of Concrete Classic lore. On the 18th tee, Bryan Willis stepped in to hit when Dean, trying to be supportive, inadvertently iced him by stopping him right before the swing to tell him how great he was going to do. Bryan promptly skulled the ball into an evergreen next to the tee box. It was such a perfect first-year moment that the group took a picture in 2019 specifically to remember it.

Legacy

Bryan Willis holding up his winnings
Bryan’s winnings pose became a recurring visual signature of victory and one of the small traditions that carried forward from the first year.

The first year established the operating system of the trip. Team formats mattered. Points determined the champion. Fox Hills worked as the home. ABC-D worked. 9x9 worked. The four-man scramble worked. Most importantly, the group discovered that the stories off the course could matter just as much as the scores on it.

Very few pictures were taken in 2018, and most of the ones that survived came from Bryan. That scarcity actually fits the year. The group was not trying to document a tradition yet. They were still discovering that they had one. But even in that small set of photos, the identity of the trip is already there: Austin at breakfast, Jake on the green, Tom holding the champion memento, and Bryan holding up his winnings in the pose that would later become a signature of his.

Every original participant except Gabe continued attending through 2022. Tom became the first champion. The breakfast crew became a routine. Bryan’s pose became part of the visual language of winning. And a miserable round in Effingham turned into the first chapter of something that clearly was not going away.

Group photo at Harborside with Bob Sieloff holding the trophy
Chapter 2

Bob Wins

2019
ChampionBob Sieloff
Points235
The chapter8 players · One unforgettable newcomer

Story

Bob Sieloff sitting at the table playing a game with reading glasses on
When Bob was still serious — for about a day and a half.

The second year started with a completely different kind of energy. In 2018, nobody knew what the trip was yet. By the time 2019 came around, everyone did. The group was excited to get back to Fox Hills, not just to play golf, but to continue something that already felt like it had momentum.

Gabe did not return, and Dean brought his brother-in-law, Bob Sieloff. From the start, nobody was quite sure what to make of him. The first night, the group played some kind of game — cards, dice, Ship Captain Crew, something along those lines — and Bob sat there with reading glasses on, taking everything very seriously. At one point, somebody broke a rule and Bob immediately shut it down. It was very matter-of-fact. Very direct. It did not exactly scream seamless fit.

The next morning did not help. Around 7:30, Dean was trying to get him moving for the tee time, and Bob yelled back, “I’m on vacation.” The idea of waking up early to play golf did not seem to line up with what he thought the trip was. Through the first day or so, it was not obvious how this was going to work.

It ended up working perfectly.

Jake kneeling next to a shot on a par 3 with Dean behind him
A 9x9 moment from a year where the competition felt much more intentional than it had in the beginning.

As the weekend settled in, Bob became one of the defining personalities of the trip. He struck up an immediate bromance with Austin, who at that point was still the young guy in the group and already one of the best players there. The pairing just worked. Austin had the talent. Bob had the steadiness and the personality. Together they became a problem.

The structure stayed mostly the same as the year before, but the difference was obvious. The formats were no longer new. People knew how to compete inside them. The trip did not feel like an experiment anymore. It felt established.

Field

Jake Willis, Andy Terry, Bryan Willis, Austin Willis, Dean Johnson, Tom Seaborg, Troy Seaborg, and Bob Sieloff.

Tournament Breakdown

The 9x9x9 format remained, with the final four-man portion still making up the last nine. Andy and Troy won the 9x9 that year. The four-man scramble was won by Bob, Jake, Tom, and Troy — another close finish in a format that always seems to be tight.

Vegas returned as well, and Austin and Bob won that one, with Jake and Dean finishing second. ABC minus D was won by Jake, Dean, Bryan, and Tom in another close result. A format called Split Ball also appeared that year, with Andy, Bob, Jake, and Tom coming out on top. Record keeping from some of those early years was not perfect, but the structure and competition were very real.

The final round changed from true alternate shot to Modified Chapman. Both players hit drives, both hit each other’s second shot, then the team chooses one and alternates from there. It gave the final round the same kind of pressure without being as punishing as full alternate shot. Austin and Bob won that final round at +27. Jake and Dean tied Andy and Troy for second at +29.

Results

  • Champion: Bob Sieloff
  • 9x9 Winners: Andy Terry and Troy Seaborg
  • 4-Man Scramble Winners: Bob Sieloff, Jake Willis, Tom Seaborg, Troy Seaborg
  • Vegas Winners: Austin Willis and Bob Sieloff
  • Split Ball Winners: Andy Terry, Bob Sieloff, Jake Willis, Tom Seaborg
  • ABC-D Winners: Jake Willis, Dean Johnson, Bryan Willis, Tom Seaborg
  • Modified Chapman Winners: Austin Willis and Bob Sieloff
“Today we’re playing Bob wins.”

Defining Moments

As the weekend went on, Bob developed a line that would outlive the tournament itself. Every time he won anything — golf, cards, whatever — it became “Bob wins.” By the end of the trip, that was no longer just something he said. It was the theme of the weekend.

The shot that best summed up the tournament came in the final round. On hole four of Red, Bob hit one essentially backwards. The hole looked dead. Austin stepped up and hit a 270-plus yard three-wood over Jake and Dean’s heads in the fairway and completely flipped the situation. It was a perfect summary of the partnership: Bob never out of it, Austin capable of erasing almost anything.

Bob still sitting inside Harborside talking while the rest of the group waits outside
Everyone else was ready to leave. Bob was still inside working the room.

The dinner at Harborside in Manitowoc added another classic trip moment. Bob had watched Making a Murderer and wanted answers. The staff was much less interested in the details than Bob was, but that did not slow him down. By the end of the night, the full group had gone outside after the picture, and Bob was still inside talking while Andy tried to get him out of there. The photo taken through the glass became one of the signature images of the year.

Legacy

Jake and Tom during the long National walk with shirts off
The National walk became less about pace of play and more about survival, conversation, and waiting.

If 2018 created the trip, 2019 gave it more personality. Bob arrived as a question mark and left as one of the defining figures of the Concrete Classic. “Bob wins” became part of the vocabulary of the trip and never really went away.

It was also the year where the stories started stacking up faster. The walk on the National dragged on forever. Dean and Bryan talked their way through six hours while the group in front finished, ate lunch, and still had time to spare. Jake took his shirt off. Tom may have eventually done the same. Austin made fun of both of them for their golf etiquette. It was the last time the group ever walked like that again.

The pictures got better too. Not just more of them, but better at capturing what the trip actually was. The group shot at Harborside. The window shot with Bob still inside. The winning selfies and posed pictures that started becoming part of the trip’s visual language. The first year had the foundation. The second year had the life.

Bob on the driving range during the beginning of Where's Bobbo
“Where’s Bobbo?” began when Bob managed to be technically in play but nowhere near where anyone expected him to be.
Bryan and Dean standing by the tree from the previous year's icing moment
The callback photo by the tree was too good not to take.
Bryan and Tom taking a post-win selfie
Bryan documenting another win — a tradition that would carry forward year after year.
Bryan laying next to his golf ball during a round
Bryan fully committing to the bit — a moment that perfectly captured how seriously nobody was taking things, even as the competition got sharper.
Austin Willis, TJ Dauphinbaugh, and Bob Sieloff after the 2020 tournament
Chapter 3

Bob Wins… Austin Wins

2020
ChampionAustin Willis
Points205
The chapter12 players · A growing field

Story

Group playing on arrival day in 2020
By 2020, the trip had evolved — guys were arriving early and already playing before the full group even settled in.

2020 was not a normal year anywhere, and for a while it was not clear if the Concrete Classic was even going to happen. Wisconsin ultimately opened things up, and with that, the trip went on. Outside of flipped cups on the greens, the golf itself felt mostly untouched.

What did change was the size of the trip. The field expanded from eight to twelve players, and that shift was immediate. Harold Billings, Caleb Billings, TJ Daughenbaugh, and Fredo Gomez joined the group, turning what had been a tight core into something noticeably bigger.

The travel day changed with it. What used to be a slow roll-in became a full day of golf. Harold, Caleb, and TJ showed up around 10:30 in the morning ready to go — hours before the rest of the group was even close to arriving. By the time things were organized, they already had holes played.

Unlike the year before, there was no single personality shift that defined the weekend. Everyone more or less fit right away. The group knew what it was by now. The only real unknown was Fredo, and even that was softened by his connection to Troy.

When the shot called for it, there was no hesitation — even if it meant stepping into the water.

The increase in players forced changes in how the golf itself worked. Pairings shifted. The usual duos split. Depth of field started to matter in a different way.

Field

Jake Willis, Andy Terry, Bryan Willis, Austin Willis, Dean Johnson, Tom Seaborg, Troy Seaborg, Bob Sieloff, Harold Billings, Caleb Billings, TJ Daughenbaugh, and Fredo Gomez.

Tournament Breakdown

2020 was the only true version of 9x9x9. The bracket format fully played out across Red, White, and Blue, with teams advancing round by round and a wildcard advancing based on score. Austin and Fredo won that event.

The four-man scramble followed, won by Austin, Bryan, Fredo, and Tom. Vegas returned for its final year, with Jake and TJ winning. Split Ball was won by Austin, Bob, TJ, and Tom. ABC-D went to Bob, Jake, TJ, and Tom. The final round (Modified Chapman) was won by Andy and Bob.

Results

  • Champion: Austin Willis — 205 points
  • Runner-Up: TJ Daughenbaugh — 195 points
  • 3rd Place: Bob Sieloff — 185 points
  • 9x9x9 Winners: Austin Willis and Fredo Gomez
  • 4-Man Scramble Winners: Austin Willis, Bryan Willis, Fredo Gomez, Tom Seaborg
  • Vegas Winners: Jake Willis and TJ Daughenbaugh
  • Split Ball Winners: Austin Willis, Bob Sieloff, TJ Daughenbaugh, Tom Seaborg
  • ABC-D Winners: Bob Sieloff, Jake Willis, TJ Daughenbaugh, Tom Seaborg
  • Modified Chapman Winners: Andy Terry and Bob Sieloff
Bob wins… Austin wins.

Defining Moments

The entire tournament came down to the final round — and even then, nobody knew who had actually won.

Austin entered the round in first. TJ sat in second. The path was simple: beat TJ and win. Jake and TJ made sure that did not happen.

But Andy and Bob won the round outright, shifting the points just enough that Austin taking third became the only scenario where he still wins — and that is exactly what happened.

Bryan sitting on his ball while Andy waits to hit
One of the most iconic photos of the trip — Bryan fully committed while Andy waits behind him.

At dinner, nobody knew the result. No app. No live scoring. Just guesses. When it finally came together, Austin had won by ten.

Legacy

2020 changed the scale of the Concrete Classic. Twelve players meant more combinations, more variability, and more ways for the tournament to unfold.

It also introduced a new kind of finish — one where the winner was not obvious, even after the final round ended.

Group smoking cigars laughing together
Moments like this started to define the trip just as much as the golf.
Printed Bob meme posters
Bob Wins became something much bigger than a phrase.
Bryan and Caleb flexing together
By 2020, personality mattered just as much as performance.
Bryan holding up his winnings in his signature pose
The Bryan money pose — equal parts victory, personality, and tradition, becoming one of the defining visuals of the trip as it evolved.
Eli Schaefer and Carson Anderson holding their winnings after winning the 2021 Concrete Classic
Chapter 4

Eli Saves the Day

2021
ChampionCarson Anderson
Points220
The chapter16 players · The first Ryder Cup

Story

Austin retrieving his 3-wood in conditions no one should have been playing in.

2021 was the largest structural shift in the history of the Concrete Classic. If the trip is the iPhone, this was the iPhone 4. The field expanded to sixteen — the number it had always been building toward — and with it came the format that still defines the trip today. Outside of the inaugural year, no chapter changed more about what the Concrete Classic is.

But the week almost started without it. Two days before arrival, a late dropout left the trip at fifteen players. With almost no time to react, a search started to find a sixteenth. Carl Flint got the call. Within an hour, he was in his car driving from Missouri to Wisconsin to join a group he had not planned on being part of. He did not just fill a spot. He saved the trip.

The returning core was strong — Jake, Dean, Tom, Bob, Austin, Troy, Andy, Bryan, Harold, and TJ — but the new additions changed the feel immediately. Eli Schaefer arrived as the youngest player in trip history at just seventeen. Carson Anderson and Jackson Dillon joined through Austin. Ryan Johnson and Johnny Mack came in with a different kind of reputation — high energy, unpredictable, and potentially disruptive. There was real concern the trip could drift into something it was never meant to be. It did not.

The opening round set the tone — just not in the way anyone expected. On arrival day, the group teed it up for ABC minus D on the National. It was late May in northern Wisconsin, but it felt like February. Rain, wind, and temperatures hovering near freezing turned the round into survival. Scores reflected it. Across a field of strong players, only Jake and Andy Terry broke 50 over the nine holes.

At one point, Austin’s hands were so cold he threw his 3-wood into a pond. He did not wait until the round ended to get it. He stripped down, swam out in near-freezing conditions, retrieved the club, and finished the round. It remains one of the most absurd — and perfect — moments in trip history.

Bob and Austin during the first night wine chaos on the balcony
The first night got wild, just not for the reasons anyone expected.

That night brought a different kind of chaos. What started as concern about Ryan and Johnny quickly flipped. They came ready to compete. The real energy instead came from Bob — who turned the upstairs balcony into a full production, pouring wine down onto Austin before taking his turn getting drenched himself. The trip had been tested in two very different ways in less than 24 hours. It passed both.

Bryan Willis, Jake Willis, and Austin Willis together during the 2021 Concrete Classic
Two generations of the trip — Bryan alongside his sons — a snapshot of how the Concrete Classic grew without losing where it started.

Field

Jake Willis, Andy Terry, Bryan Willis, Austin Willis, Dean Johnson, Tom Seaborg, Troy Seaborg, Bob Sieloff, Harold Billings, TJ Daughenbaugh, Eli Schaefer, Carson Anderson, Jackson Dillon, Ryan Johnson, Johnny Mack, and Carl Flint.

Ryder Cup

In 2021, the Ryder Cup arrived — and immediately became the flagship event of the trip.

2021 introduced what would become the centerpiece of the Concrete Classic: the Ryder Cup. Sixteen players split into two eight-man teams. A captain for each side. Morning best ball. Afternoon alternate shot and singles. Nine total points. First to five wins.

Tom Seaborg and Bob Sieloff served as the inaugural captains. Team Tom — Andy, Carl, Jake, Johnny, Ryan, TJ, Tom, and Troy — won the first Ryder Cup, establishing what would quickly become the most anticipated event of the week. It was immediately clear this was not just another format. This was the format.

Tournament Breakdown

ABC minus D resumed the next day under normal conditions, though the scores still reflected how brutal the start had been. Bryan, Carl, Harold, and Troy won with numbers that would normally be nowhere near the top — a reflection of just how extreme the first round was. The lowest score on their winning team was 105.

The 9x9 evolved into two flights for the first time. In the A Flight, Jake and Bryan delivered one of the most meaningful wins in trip history, posting the lowest round and winning the bracket together. In that same match, Eli announced himself. From 150 yards, at seventeen years old, he holed out for eagle — a shot that immediately cemented him as a factor on the trip.

The B Flight was won by Johnny Mack and TJ Daughenbaugh — a breakthrough moment for Johnny that marked the beginning of his real competitive presence. The four-man scramble was won by Bob, Dean, Jake, and Ryan. Ramble & Scramble — the format where one player plays his own ball while the other three play a three-man scramble and the two scores are combined — was won by Austin, Bob, Carson, and Johnny, giving Carson his first event win.

The final round changed permanently in 2021. Vegas was removed. In its place came a true aggregate format — two-man teams, both scores counting. Carson Anderson and Eli Schaefer won the final round. Eli shot an 84, one of the best rounds of the week, and the duo finished two shots clear of Austin and Carl and three ahead of Ryan and Tom.

Carson finished the tournament with 220 points, powered heavily by a large final-round award. He joined Bob and inaugural champion Tom among the players who won on their first trip. The original 2021 awards remain unchanged: applying the later point schedule would change that year’s champion.

Results

  • Champion: Carson Anderson — 220 points
  • ABC-D Winners: Bryan Willis, Carl Flint, Harold Billings, Troy Seaborg
  • Ryder Cup: Team Tom
  • 9x9 A Flight Winners: Jake Willis and Bryan Willis
  • 9x9 B Flight Winners: Johnny Mack and TJ Daughenbaugh
  • 4-Man Scramble Winners: Bob Sieloff, Dean Johnson, Jake Willis, Ryan Johnson
  • Ramble & Scramble Winners: Austin Willis, Bob Sieloff, Carson Anderson, Johnny Mack
  • Final Round Winners: Carson Anderson and Eli Schaefer
The modern Concrete Classic started here: sixteen players, Ryder Cup, permanent structure.

Defining Moments

This year produced more than one defining moment, but the one that gave the chapter its name came from Eli. At seventeen years old, in his first trip, he holed out from 150 yards for eagle during the 9x9. It was not just a great shot. It was an arrival.

The Austin pond swim will always live near the top of the list, but so will the first Ryder Cup, the first night balcony chaos, and Jake winning the A Flight alongside his dad. 2021 felt like a week where the trip stretched into its full size without losing the thing that made it special in the first place.

Eli’s hole-out eagle at seventeen years old felt like more than just a great shot. It felt like the future arriving early.
Jake, Dean, Ryan, and Bob posing with winnings
The four-man scramble winners: one more example of how quickly the larger field raised both the ceiling and the energy of the trip.
Champions wearing blue polos after the 2021 event
The blue champions polos became part of the trip’s visual identity — another tradition that started once the event reached full scale.

Legacy

Jake and Harold together during the 2021 trip
By 2021, the trip was no longer becoming something. It had become it.

2021 established the modern Concrete Classic. Sixteen players became permanent. The Ryder Cup became the centerpiece. The final round format evolved into what it is today. The structure locked in.

But more importantly, the identity held. The trip absorbed new personalities without losing itself. Competition intensified without breaking culture. And a new generation of players arrived — not just to participate, but to win.

For Jake, the year carried something more personal. Winning the 9x9 alongside his father became one of the most meaningful moments the trip has ever produced. In the years that followed, those pictures — once just part of the weekend — would take on far greater significance.

The trip had grown up. And it was not slowing down.

Full 16-man group photo from the 2021 Concrete Classic
The full sixteen-man group — the number the trip had always been building toward.
Bryan in his classic money pose with Jake beside him
The Bryan money pose returned, this time with Jake in the frame — one of the year’s strongest images.
Bryan Willis with his mouth open in a candid moment
One of the great candid Bryan photos — the kind of image that started carrying more weight as the years went on.
ABC minus D winning team from the 2021 Concrete Classic
The ABC minus D winners survived the ugliest scoring conditions the trip has ever seen and still found a way to win.
Team Jake celebrating around the golf cart with the American flag after winning the 2022 Ryder Cup
Chapter 5

It Pays to Be Number 2

2022
Kevin arrives, the brothers become captains, and a Ryder Cup comeback produces one of the trip’s defining photographs.
ChampionKevin Pacholski
Points267
The chapter16-player field · A new schedule

Story

Jake and Tom taking a sunset selfie after the 2022 Ryder Cup
Jake and Tom at the end of Ryder Cup day, with the sun setting behind them. A comeback, a playoff, and one more winning photo together.

For four years, the trip had competed with Memorial Day. Guys wanted to get home for the holiday, and a Thursday-to-Monday schedule kept running into that reality. In 2022, the group moved to the Wednesday through Sunday afterward. It was a practical change that ended up changing the competition, too.

The new dates finally made it possible for Kevin Pacholski to come. Austin and Troy had spent years trading places behind Jake, but Kevin arrived as a clear number two. For the first time, Jake had another golfer in the field who played in his stratosphere. Kevin was not coming just to fill a spot.

He started winning immediately. But the week’s biggest story would involve a coin flip, two brothers, and a team that looked a lot more comfortable before the Ryder Cup started than it did at lunch.

The brothers become captains

Two Team Jake players in matching flag shirts, flag trousers, patriotic cowboy hats, and sunglasses
Flag shirts, flag trousers, and patriotic cowboy hats—the morning pairings did not do the USA theme halfway.

Jake and Austin were the captains. Jake won the coin flip, chose to pick first, and took Kevin. With Caleb helping Jake and Bob helping Austin, the rivalry had plenty of familiar faces around it. Jake’s side liked its chances. Having the two best golfers on the same team will do that.

The outfits added another layer. Team Jake went all-in on USA gear, even coordinating the morning pairings. Austin’s team wore Iowa colors, a little jab at his Illinois brother. The Cup had only existed for a year, but guys were already treating it like something worth dressing for.

Then Team Jake went down 3–1. Jake and Dean were the only morning pairing to win. The one-two punch was still there. So was a very real possibility that it would not be enough.

In the afternoon, Jake and Caleb sent out Dean and Harold first to see what Austin would do. He put Bob and Jim against them. That looked like a match Team Jake might have to give away while finding its points somewhere else. Instead, Dean and Harold halved it. Kevin still had to get past Troy, who took him to seventeen holes, but that unexpected half kept the comeback alive. The Cup finished tied for the first time.

Team Jake posing outside the villa in coordinated USA uniforms before the Ryder Cup
Team Jake outside the villa before the Ryder Cup. The coordinated USA uniforms were ready; the comeback from a 3–1 deficit was still ahead of them.
Team Austin posing outside the villa in black and gold Iowa uniforms
Team Austin outside the villa in Iowa black and gold. With Jake’s Illinois loyalties on the other side, even the uniforms joined the brothers’ rivalry.

A putt over the water

Jake standing on a golf cart holding the American flag after Team Jake won the Ryder Cup playoff
Jake flying the American flag from the cart after the playoff win. The long birdie putt over the water had turned a morning deficit into a celebration.

With no precedent to follow, the captains settled on a three-hole, four-man scramble playoff. Both sides tied the opening par five on White. Then came the par three over the water.

Jake was putting last. He holed a long birdie putt, and Austin’s side made par. One more hole still had to be played, but that was the moment the comeback felt complete. Team Jake finished the job.

The picture afterward became one of the trip’s defining images: Jake holding the American flag, his teammates gathered around the golf cart in their USA outfits. The rivalry, the uniforms, the unlikely half, and the playoff all ended up in one photograph. The Ryder Cup had found its identity.

It was not the only late putt that week. Harold holed a huge one on White seven as darkness approached to win the four-man scramble for Kevin, Caleb, Tom, and himself. Around the start of that playoff, Ryan appeared in a golf cart. His honeymoon plans had changed, and he had come to replace Jim for the final day. Nobody knew he was coming. The timing made him look like a knight in shining armor.

Dean Johnson playing a playoff approach beside the water with Eli Schaefer and Johnny Mack watching
Dean hitting his approach during the four-man scramble playoff, with Eli and Johnny watching. The playoff would eventually end with Harold’s long winning putt on White seven.
The guys drinking shots together from a long wooden shot board on the golf course
The guys line up for shots off the board. One board, several drinks, and not much chance of a quiet celebration—the golf was competitive, but the finish had its own kind of chaos.

It pays to be number two

Kevin Pacholski in the green jacket holding the championship trophy after winning on his first trip
Kevin with the green jacket and trophy after winning on his first trip. The newcomer who arrived as the number two golfer left as the champion.

Kevin and Harold became an unlikely but remarkably effective partnership. They closed the week by winning the final round together, and Kevin left his first trip as champion. He had won almost everything he entered, joining Bob and Carson among the newcomers who arrived and immediately took the title.

Dean Johnson holding the on-course prize markers after winning the closest-to-the-pin prizes
Dean showing off the on-course prize markers. He took home the closest-to-the-pin prizes alongside a week that included helping keep the Ryder Cup comeback alive.

Bryan had his best trip, too. He won alongside Kevin in the opener, won the B Flight with Carson, and finished third overall. He was playing well and helping different teammates all week. Nobody knew it would be his last trip.

2022 gave the group a stronger field, a schedule that worked, and a Ryder Cup finish that still stands among its best. It also gave Bryan one more full week in Mishicot—with his sons, his friends, and his best golf of the trip.

Chapter 6

For Bry

2023
A week of support for Bryan, three memorable newcomers, and a championship Jake would share with his dad.
ChampionJake Willis
Points235
The chapter16 players · The Concrete Classic finds its name

Story

By the time the group returned to Mishicot in 2023, the trip meant something different. Bryan Willis had been diagnosed with brain cancer the previous November. He had been there every year since the beginning. Now, for the first time, he could not come.

Jake and Austin were not sure they would make it either. Their dad had spent about a month in the hospital, and leaving depended on how he was doing. He improved enough for them to go on Wednesday. On Friday, while they were away, Bryan finally came home.

The name Concrete Classic grew out of his diagnosis. Bryan was a concrete finisher by trade, and the trip became a way to honor a man who had helped give it its personality. He was a competitor, called things as he saw them, and never met a stranger. Even in his absence, he was everywhere that week.

Team Bryan wristbands were on wrists throughout the group. Harold arranged shirts and ribbons, and Team Ryan wore the tribute shirts in the Ryder Cup. Jake made a video for his dad. These were gestures of support, with everyone still hoping Bryan would return to Mishicot one day.

Three guys who belonged

Jeremy Flint, Reed Tomsheck, and Garrett Gusloff arrived together, and all three were home runs. Jeremy, Jake’s oldest cousin, added depth near the top of the field. Reed had wanted to join his friends Ryan and Johnny for two years. Garrett came as Jake’s close friend and longtime coworker. They brought different games and personalities, but each found his place.

Garrett’s golf took longer to settle in. His opening round was rough, and the introduction to competitive golf left him discouraged. By Saturday, the same player would be helping decide the championship.

The improvement was not limited to the newcomers. Dean’s rebuilt swing produced a 100 in the opener and helped Jake, Tom, Dean, and Bob win together. Ryan broke 100 in every own-ball round. Guys were putting work into their games, and it showed. The trip was still full of jokes and familiar personalities, but it was becoming a better golf tournament.

Best friends, opposing captains

Ryan and Johnny became Ryder Cup captains, bringing the kind of rivalry only best friends can provide. Team Ryan won the outfits. Team Johnny won the Cup. Jake and Tom were part of the afternoon alternate-shot sweep that settled it, and Johnny left with bragging rights Ryan was not going to hear the end of.

The scoring app changed the experience, too. Now guys could follow what was happening elsewhere instead of waiting for everyone to get in. Caleb, home with a new baby, followed the entire trip from afar. The group had its first spectator—and he was watching closely.

One stroke

Jake and Tom spent much of the week playing well together. In the final round, they had to play against each other. Both entered with a chance to become champion. Tom had Andy, a reunion of the partnership that won the inaugural trip. Jake had Garrett.

Garrett came out strong. The player who had struggled so badly on the first day was suddenly giving Jake exactly what he needed. Tom and Andy stayed right with them, and other teams were close enough on the app to keep every hole uncomfortable. Jake watched the scores. Garrett would rather not know.

On seventeen, Jake and Garrett found trouble off the tee. Garrett took a drop, then hit two of his best shots of the week to get back in position. Jake was about 250 yards out with a decision to make: lay up, or keep his foot on the gas? Garrett told him to go for it. Jake hit a three-wood pin high.

Garrett salvaged a seven. Jake made birdie. They took a narrow lead to the last hole and held on to beat Tom and Andy by one stroke. After years of knocking on the door, Jake had finally won.

Tom and Andy had not given an inch, but they were among the first to hug him and say how happy they were for him. Kevin gave a speech Jake would never forget. Caleb called from home. The competition had been real all the way through, and so was the happiness for the guy who came out on top.

For Bry

Jake FaceTimed his dad after the win and cried while sharing the news. Bryan, finally home from the hospital, asked why he was crying. A game could feel small beside everything the family was facing, and still mean an enormous amount.

Jake came home Sunday and told Bryan about the trip. On Monday, June 5, Bryan passed away—two days after his son’s championship.

The group had gone to Wisconsin hoping he would join them again. Instead, that week became the last championship Jake could share with him. The wristbands, the shirts, the calls, and the win took on a meaning nobody could have known when the trip began.

2023 changed the Concrete Classic. The golf kept getting better. Three new guys became part of its future. But the year belonged to Bryan, and to a group that showed how much it loved him.

A Letter From Your Champion Jake’s complete message to the group · 2023

In the final round I told Garrett, it’s hard to believe how a simple meaningless game can mean so much. You guys did an incredible job with everything. I apologize for the length but I have a lot to say.

First and foremost, I would like to thank Harold for putting together the Team Bryan shirts and the ribbons. I absolutely loved them. I think in future years we will make a point to all have one or possibly 2 separate colors and make it the official Ryder Cup shirts? Each team with a different color? Most of you don’t know but our dad came home while we were on the trip after 4 weeks in the hospital. I told him about the trip today and he really enjoyed hearing about it. It’s been a long journey that’s not done but please keep praying and hopefully Bryan will return to Mishicot one day.

I thank both of our Ryder Cup Captains as they brought all the drama that we’d expect from best friends. Team Ryan may have won the outfits, but Team Johnny won overall. Never forget that Ryan.

Bob Wins… *Bob Swims!

This is a very fun trip, but this is a golfers trip and it showed. It’s obvious that everyone has made a point to improve their game and I am very proud. Dean-O took close to 12 strokes off his trip average and shot his best trip round by 14 strokes. Dean has rebuilt his swing and I think everyone agrees he has arrived. Ryan shot every round under 100, all being the first time he’s ever broke 100 in Mishicot. Eli shot 78 in the final round which is the 3rd best score ever on the trip and has solidified him the number 3 spot. We’ll see how long Kevin will keep him from the 2 spot lol. Troy got back into the mid 80’s in the final round and I’m sure he’d tell you he could have shot a few strokes better. Austin got back into the 80’s after a 2 year hiatus. Tom shot 7 strokes better than his average. Andy shot his best round ever… More on that to come. Bob refuses to give up strokes to the field keeping his average for the year at 100 which is top half of the field. Johnny shot his best round ever on the trip which was one lower than Ryan’s lowest if we’re still keeping score. The Kevin and Harold duo still is lights out.. more to come. The Carson Reed duo was incredible. I didn’t see that one coming. Austin Troy took care of business in the scramble, would still like you 2 to play me and Tom. Austin and his ramblers played well. Just a lot of great golf. I am so happy that everyone keeps improving on their game, which makes the trip just a bit more fun.

Our 3 new guys were an absolute pleasure to be around all week. Jeremy, Garrett, and Reed all played great meaningful golf and all played a huge part in numerous victories. They were also 3 of the best guys we’ve ever had.

The app will be here to stay. How we rank players with pass trip rounds will now be the previous two years and the current year. So guys with six years of golf will not be plagued if they have improved.

The final round: Winston Churchill once said that “history is written by the victors”, so I’ll tell the story of the final round lol. Right out of the gate I knew it would be a dawg fight. 2 champions in the final group, one paired with Troy who could firmly take second. The Kevin Harold duo in effect, the rebirth of Ryan and Carl but this time with his better golfing offspring Jeremy. Final Round Eli and a new Dean paired with who I was told was the record breaking cart in drinks drank for a round in Johnny and Bob. Finally the reload of the first winning final round duo in Tom and Andy. So the fight was on. I am a huge score watcher, which wasn’t ideal for Garrett who didn’t really want to know. Anyways, Garrett comes out of the gate like a 2019 Bob. He torched the first 6 holes. Meanwhile I was +3. Meanwhile Andy and Tom are lock step with us through 9. After 9 we see Jeremy and Ryan are up but we’re still in it. Troy and Carson stayed in it until we hit like hole 17. At hole 17 the I think Tom and Andy would agree the nerves hit an all time high. Both of them hit well off the tee, Garrett and I had one in the trees and one by the cart path. Garrett hit 2 of his best shots of the trip after taking the drop. Lovely 6 iron back into the fairway, and hybrid from 220 which rolled over the green to the back rough. I was around 250 out, had hybrid in hand. I told Garrett think we lay up or keep the foot on the gas? He said gas it. We hit 3 wood pin high. Me and Tom had identical chips, both hit on in a decent spot. Garrett took the best 7 you’d ever seen after the early drop. We then hit birdie on my ball which got us a 2 shot lead. I knew Jeremy and Ryan were in with +44 but I didn’t think it would matter with how Andy and Tom were playing. I knew one of us would beat it. Long story short, Me and Garrett went +2 on the hole which kept us better than Tom and Andy going +1 and Ryan and Jer’s +44. We did it. Garrett played incredible in the final stretch. Tom and Andy played incredible, shades of 2018. Andy shoots 90 which is his best score ever and first time back in the 90’s in 3 years. The hugs from those 2 after just showed how great this trip is. They didn’t give an inch but were the very first to tell me how happy they were for me. I took a FaceTime call with our first ever spectator in Caleb who tracked the entire trip all weekend while holding that new baby. How great was the app?! I am so grateful that we have the group of people we do. Thank you to Kevin for your wonderful speech, it’ll never be forgotten. I will be taking our lovely jacket and trophy on tour, I’ll try to update you on the places that it ends up.

I love all of you. Thank you for a great trip, thank you for loving golf. God Bless all of you and God Bless the Concrete Classic.

Chapter 7

The Brotherly Shove

2024
A trophy carries Bryan’s name. A new peer-selected award honors improvement. Austin returns to the top.
ChampionAustin Willis
Points227.5
The chapter16 players · The Bryan Willis Trophy

Story

A year after Bryan’s passing, the group returned to Mishicot with a way to make his place in the trip permanent. Jake had a new championship trophy made: a deer, honoring his dad’s love of hunting, bearing the Bryan Willis name. Austin had banners made and a presentation planned.

Jake stood outside in his green jacket while Austin began upstairs, walking through the chapters of the trip and lowering the banners from the back of the villa. On the balcony, Austin held it together. When he came downstairs and stepped outside to the group, the emotion caught up with him. It caught up with everyone else, too.

Austin presented the trophy to Jake as the reigning champion. His brother had won just before their dad passed away. Being the first to hold a trophy named for Bryan felt fitting. It would also be brief.

Old friends, new traditions

For the first time, everyone in the field had been on the trip before. Caleb was back after following 2023 from home with a new baby, and Carl returned as well. There were no introductions to make. The group already knew one another.

The old championship trophy found a new purpose. With a new plaque, it became the Dean Johnson Most Improved Golfer Award, selected by the players themselves. Caleb won the inaugural vote. He had missed 2023, but the difference between the golfer who left in 2022 and the one who returned in 2024 was clear to his peers.

Caleb also captained the Ryder Cup against Troy. After the tribute shirts the year before, his side was determined to make its own impression. The camouflage uniforms did that, and the golf backed them up. Team Caleb won 6–3, the most decisive Cup to that point.

A final round in the rain

Dean reached the final day with the lead and a chance to win the championship he had been chasing since the first trip. Jake was right behind him. Jake wanted to repeat, but if he could not win, he wanted it to be Dean.

The rain made the final round difficult, and Dean and Kevin could not find the golf they needed. Jake played with Carl, who was playing well. In front of them, Austin and Andy were doing the same. The scores on the app kept pulling Jake’s attention forward.

Much of Jake’s round was among the best golf he had played on the trip. Hole eleven was the exception. An ill-advised shot from the beach helped turn it into an eight, with two balls finding the water. He stayed in the fight, but on eighteen he needed to attack. That ball found the water, too.

Austin and Andy finished three strokes ahead of Jake and Carl. Andy had helped Tom win the first trip and had nearly helped him win again in 2023. Now he had helped another Willis brother take the title.

The Brotherly Shove

Austin was champion again, four years after his first win. His game had slipped from that earlier form, but he had played well when it mattered, in weather that had taken plenty of others out of contention. Jake had come close to repeating. Austin pushed him out of the way.

The trophy presentation began the week with one brother holding Bryan’s name. The championship ended it with the other. Jake’s win came just before their dad passed away; Austin’s came on the first trip afterward. The Brotherly Shove had its rivalry, but underneath it was a connection neither brother could miss.

Chapter 8

A Tale of Two Champions

2025
A late addition reshapes the Ryder Cup, Dean calls his shot, and the week ends with two champions.
ChampionGarrett Gusloff & Caleb Billings
Points195 each
The chapter16 players · The first shared championship

Story

After a year with no newcomers, 2025 brought Big Jeff. Jeff Peterson had played sanctioned events with the group the previous fall, so several guys already knew his game. His short game was outstanding, his golf was steady, and he arrived as the number two player behind Jake.

He also arrived late, replacing Harold. That mattered immediately. Dean and Andy had already drafted their Ryder Cup teams, and substituting Jeff for Harold changed the balance considerably. Troy moved to Team Dean, Reed went to Team Andy, and the Cup had its first trade.

Behind the scenes, the trip was becoming more organized. Garrett had taken over the money as treasurer, and Jake had sent the Constitution of Golf to the committee for approval. What began as a weekend idea now had enough moving parts to need a structure of its own.

Dean gets his comeback

Dean and Andy were finally opposing captains. Both had been there from the start, but Dean’s improvement had narrowed the gap enough to give their rivalry the competition it deserved. Jake served as Dean’s assistant.

The morning looked familiar. Jake and Dean won, everyone else on their side lost, and Team Dean went to lunch down 3–1. Jeff and Reed had rolled Caleb and Tom. The late replacement was making his presence felt.

Dean and Jake borrowed the opening move from 2022: send out a pairing and see how the other side responds. Dean and Garrett drew Austin and Jeremy, who won. That left no room for another loss.

When Jeff and Bob came out in alternate shot, Jake wanted the match. Wherever Jeff went, Jake was going, with whatever partner Dean chose. Dean gave him Tom. They won. Caleb and Troy won theirs, and Eli and Ryan delivered in singles. Team Dean had come all the way back to win 5–4.

Watch this

Garrett put himself in championship position by winning both scramble events on the same day. Caleb stayed close. Then Ramble in the Scramble went to a playoff, and Dean supplied one of the year’s best moments.

Jeff made birdie playing the solo ball. On the scramble side, Dean was the last to face a bunker shot of about thirty yards. “Watch this,” he said. Then he stuck it beside the pin. The birdie that followed gave Caleb, Dean, Jeff, and Tom the playoff win. Calling the shot would have been funny either way. Pulling it off made it unforgettable.

The final round did not belong to the leaders. Andy and Eli, playing in the first foursome, set a standard nobody else could reach. Ryan and Jeremy finished right behind them. Eli’s golf that week also earned him the Most Improved award.

Farther back, Caleb and Tom had started unevenly. Jake, playing alongside them, reminded them they were still in it. Tom picked up his game down the stretch and helped Caleb finish just high enough to keep the championship in reach. Garrett and Kevin had played a solid round of their own. Once everyone was in, the title was not as settled as it first appeared.

A tale of two champions

After Jake got home and audited the points, Garrett and Caleb were tied. They had played on different final-round teams and reached the same total through different weeks. There was no agreed overall tiebreaker that fairly separated two individuals competing in nothing but team games.

The group talked it through, including the two players involved, and decided both should be champions. Garrett and Caleb were happy to share it. The trip had its first co-champions.

Caleb had gone from following the trip at home to Most Improved to champion. Garrett had gone from a discouraged newcomer in 2023 to a champion and one of the people helping run the tournament. Neither needed the other’s win taken away for his own to matter. Chapter 8 ended with two guys who had earned it.

Chapter 9

The Fall of Tom

2026
An unfamiliar field, Andy’s fifty-yard eagle, and a final-round partnership that changes the championship.
ChampionJake Willis
Points242
The chapter16 players · A second championship

Story

Chapter 9 started with a lot of familiar faces missing. Dean’s appendix nearly ruptured just before the trip, and surgery kept him home for the first time since the beginning. Ryan and Johnny were home with babies. Caleb and Garrett were absent, too. The trip had two reigning champions, and neither was coming back to defend.

Carl stepped in for Dean, and four newcomers joined the field: Jason Flint, Mauricio Santiago, Brennan Bryan, and Max Petrungaro. Jason added to the family contingent. Mauricio finally made the trip with his best friend Troy. Max brought another strong game near the top of the field and spent the week looking simply happy to be there.

The newcomers fit. Jake, Andy, Max, and Jason won the opener together. What looked like a year of disruption was already producing a few new combinations worth keeping.

The Cup goes the distance

Garrett had been scheduled to captain against Reed, so Tom took over in his absence. Andy also had to leave for his daughter’s graduation during the afternoon, meaning Tom’s side would have to concede a point. There was little room for anything else to go wrong.

At one point in the morning, the team appeared to be down in every match. Jake and Carl had their hands full with Jeff and Reed, while Austin and Kevin were working through a close match of their own. They recovered to split the morning. On the other side, Troy played out of his mind alongside Jason.

The afternoon came down to Jake and Jeff. Jake said as much when they teed off, and the match made him play every hole to prove it. Jeff pushed him all the way to the last green. Jake barely got through, and Tom’s side won the Cup 5–4.

Three holes to remember

Jake and Jeremy were paired again in the two-man scramble. They improved on the previous year’s last-place finish, but third was still third. That put them with Andy and Jason for the four-man event, where the afternoon took a very different turn.

They birdied seven. Then they birdied eight. By nine, they believed a par would put them into a tie. From about fifty yards out, Jason played first. As Andy stepped up, Jake turned to Jeremy and said he had a feeling Andy would hit it close.

Andy holed it for eagle.

Birdie, birdie, eagle. Three holes, one win, and a celebration that made the shot an instant part of trip history. Andy had done better than anyone was asking him to do.

The Fall of Tom

Tom won Ramble in the Scramble and went into the final round in control of the championship. Jeremy was his partner, with Jake and Brennan chasing them. For sixteen holes, Tom and Jeremy played well enough to keep it that way.

Jake approached the day as a teammate. Brennan was one of the least experienced players in the field, and helping him save strokes offered more than trying to produce a spectacular round alone. The partnership worked. They enjoyed playing together, and Brennan kept getting better.

Then seventeen and eighteen changed everything. Tom and Jeremy both found the water on seventeen. On eighteen, Tom took another big number. A championship that had looked like Tom’s was suddenly available.

But Austin and Mauricio had already posted a good score. Getting past Tom and Jeremy was not enough: Jake and Brennan needed to get past them, too. Brennan made bogey on the last, one of the most important bogeys the trip has seen. Whether he knew everything riding on it or not, it was exactly what the team needed.

Jake and Brennan won the final round by one stroke. Jake became champion for the second time. Brennan had improved eighteen strokes from his Ryder Cup round on the same course two days earlier, and his last hole had helped decide the whole trip.

A different group, the same trip

Reed left with the Most Improved award after breaking 100 for the first time on the trip—and doing it twice. He had been part of the new class in 2023. Now he was a captain, an award winner, and an established part of the group.

2026 began with absences and replacements. It ended with Andy’s eagle, a Cup decided on the last green, and a newcomer helping Jake win another championship. The field had changed. The kind of moments it produced had not.