Inspired by Chris Moneymaker’s impactful win in the 2003 World Series of Poker Main Event, Kirk “Pudge” Caldwell, Steven Kerr, and their group of poker buddies assembled a satellite to send one of them to a $1,500 bracelet event at the 2011 WSOP. Winning the seat, Caldwell made the journey to Las Vegas to live out every poker player’s dream.
Las Vegas, Nevada (March 25, 2025) - Native Canadians residing in Orangeville, Ontario, along with their love of poker it is unsurprising Kirk “Pudge” Caldwell and Steven Kerr have a deep affection for hockey as well.
During the National Hockey League (NHL) lockout of 2005, Caldwell, Kerr and their group of friends suddenly needed something to pass the time with the sudden lack of hockey games to watch.
In the absence of NHL games, TSN, the channel where Canadians tune in to watch hockey action, began airing footage from some of the most notable Main Events in World Series of Poker (WSOP) history.
Suddenly exposed to some of the best moments that helped trigger the Poker Boom, it was only natural Kerr would have the idea to start a poker group.
“TSN started playing the Chris Moneymaker year when he won the Main Event. Some of us watched it and saw this accountant win a satellite then win $2.5 million dollars,” Kerr recounted. “After that they started showing Greg Raymer’s win where he won $5 million dollars, so I just started a group in my basement where we played poker.”
Orangeville, Ontario’s very own Kirk “Pudge” Caldwell.
Initially starting with ten players, Kerr’s poker group, which they refer to as OPT for Orangeville Poker Tour, regularly played with Caldwell eventually joining in 2009.
As the group grew, the collective progressively started taking the game more seriously, with Kerr beginning to look at tournament structures and considering running satellites to events at the WSOP.
In 2011, the group played their first satellite, a $150 buy-in amongst ten players with the winner receiving a seat to a $1,500 event.
Recounting the inaugural WSOP satellite of the OPT, Caldwell and Kerr shared how a fellow player from the group, Greg, had to spot him for the buy-in.
Exchanging the $150 buy-in for an additional 10% of equity if Caldwell won the seat, Greg’s generosity would pay off after Caldwell defeated Kerr heads-up to punch his ticket to the WSOP.
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Joined by Kerr and a number of fellow OPT players, Caldwell made his way to the Rio in Las Vegas in 2011 to play not only in his first WSOP event, but his very first poker tournament ever in a casino.
Playing his first poker tournament with his OPT members having a 20% share of his action (plus Greg’s additional 10%), Caldwell recounted the swings he experienced during Day One of the $1,500 event.
“The first few hours before the first break was a roller coaster,” Caldwell said. “At first break I was down to 1,100 chips, back when we started with 4,500. After break it just turned around from there, I went crazy after that.”
Not only did Caldwell advance to Day Two, but Kerr, who was also playing the tournament, bagged Day One as well.
Celebrating their early success over drinks at the end of Day One, the duo likely had no idea what laid in store for them.
Continuing his momentum into Day Two, early in the day Caldwell successfully reached the money in his very first WSOP event.
“I was ecstatic,” Caldwell said. “I had made my money back, so I was like ‘okay now lets have some fun’. I was playing for the money at that point, I didn’t care about the bracelet. I was flat broke when I went down to play, so from there I was just looking at pay jumps.”
Cashing a WSOP event, especially when it is your very first, is certainly an accomplishment, but the best was yet to come for the Canadian poker player.
Securing a cash himself, once eliminated Kerr made his way over to Caldwell’s table to rail him for the remainder of Day Two, and watched him play his way to yet another bag.
Already hitting a substantial pay day considering he had satellited into the event, Caldwell ended Day Two with an average stack, and looked to make even more money the next day.
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Joining the other 53 poker players who remained at the start of Day Three, Caldwell was on a deep run and the precipice of reaching the final table.
Getting “hit by the deck” and continuing to crack premium pocket pairs from opponents, Caldwell paired his luck with shrewd play to eventually make it to the final table.
Racking up and making his way to the final table, Caldwell told the WSOP Media Team how all of the great luck at the poker table could not save him from bad luck off of it.
“I was nervous as hell, I even dropped all of my chips on the floor,” Caldwell said. “I tripped over one of the cables, it caught me and my whole tray of chips went flying! Everybody was trying to pick up my chips.”
Gathering every one of his strewn about poker chips, Caldwell eventually arrived at the final table for the climax of the $1,500 event.
“I was nervous of course, but I was just enjoying the ride. At that point I had already won $60-70 thousand dollars, so anything more was just a bonus.”
Kirk Caldwell at the final table during the 2011 WSOP.
As the first few players were quickly eliminated at the beginning of the final table, Kerr recounted how Caldwell continued coming up to him on the rail to ask how much money he had earned.
“‘So what am I guaranteed now?’ I’m not telling you right now! It’s a lot of money, just play poker right now.”
Running hot and continuing to get dealt strong hands, Caldwell dominated the final table as one by one players were eliminated.
“I just kept getting good hands, the cards were rolling,” Caldwell said. “It’s easy poker when you’re getting hit by the deck. I was just playing poker and having fun.”
Watching his buddy from the rail, after every big hand Kerr and the rest of Caldwell’s supporters understandably hooted and hollered in support.
At one point, tournament staff instructed the rail to quiet down, as WSOP legend Phil Hellmuth
was playing at a final table in the nearby Thunder Dome.
Even as he began to doze off when there were lulls in the action, there was no way Kerr was going to leave the rail as he supported his poker comrade.
Following the elimination of Marc-Etienne McLaughlin in 3rd place, all that stood in the way of the bracelet and $668,276 for Caldwell was heads-up opponent Corbin White.
In 2011, the WSOP adhered to hard stop times for tournaments, and at the start of heads-up play only 42 minutes remained before the Tournament Director would instruct the two players to bag for the evening.
With only a few minutes left in the level, tournament staff told both Caldwell and White that they would only play three more hands before ending play.
After three full days of grueling WSOP action, Caldwell was dead set on either winning or losing the tournament that evening.
“I’m not coming back tomorrow.” Caldwell announced to all in attendance.
Sticking to his word, following a preflop three-bet from White, Caldwell moved all-in.
Looking down at ace-queen offsuit, White made the call and was flipping with Caldwell’s pocket eights.
With his pocket eights holding through the entirety of the runout, the reserved Caldwell let out a joyous shout as he threw his hands in the air, officially becoming a WSOP champion in the very first tournament he had ever played in a casino.
Jumping the rail and embracing Caldwell, Kerr enthusiastically congratulated his friend as they began their night of celebration.
Kirk Caldwell posing with Steven Kerr (right), other supporters, and his WSOP bracelet.
With play ending at 2 o’clock in the morning and the two hour time difference between Las Vegas and Ontario, friends and family back home would wake up to see that Caldwell had taken down the $1,500 event to win $668,276 and the bracelet.
Returning home from the WSOP, Caldwell would eventually use his winnings to buy himself a house and a car as well as put some aside for a rainy day.
The nine other players in the OPT group, with the 20% equity they shared, each earned $8,000 from Caldwell’s win, with Greg earning even more after spotting him $150 for the initial satellite buy-in.
Since Caldwell’s bracelet victory, the OPT continues to play regularly, growing in size with sometimes up to 70 players participating, each trying to earn their own chance at WSOP glory and recreate their friend’s magical run in 2011.
“Sometimes we have to use the basement, living room and kitchen,” Kerr said. “Me being the Tournament Director running it, I’m always trying to do it right, so I’ll be running up and down the stairs breaking tables!”
While Caldwell’s bracelet victory in 2011 certainly changed the OPT forever, the group’s love for poker was something that existed prior and continues to this day.
Regardless of whose house they play at and who is in attendance, the group continues to enjoy the community they have maintained and creates lifelong memories through their shared love of poker.
While no one from OPT has yet to recreate the success Caldwell had at the 2011 WSOP, after countless hours spent at the poker table having fun times with friends, it’s fair to say every member of the group has turned out a winner regardless.