New Jersey Poker Player Jeremy Sissman Pursues the Ambitious ‘25 Wins of Christmas’ Poker Challenge
The Origin of the ‘25 Wins of Christmas’ Poker Quest
Jeremy Sissman, a dedicated New Jersey poker pro and father of two, has set out once again to conquer his unique “25 Wins of Christmas” challenge—a personal mission inspired by PokerStars’ 25 Tournaments of Christmas promotion introduced in 2022. Rather than simply entering 25 events, Sissman aims to claim outright victory in 25 separate tournaments before December 26. Having accomplished this feat in 2022, he narrowly missed the mark last year but is determined to go the distance in 2024, tackling tournaments on PokerStars, BetMGM, and Global Poker platforms.
Sissman explains the difficulty of his pursuit: “The tournament field sizes are even bigger this year, making it even harder, but I have a few tricks up my sleeve. I just have to get first place in 25 tournaments before Dec. 26, and the fields need to have at least 25 entrants. Although, the smallest fields I’m playing are generally around 50 players.”
Inside the Grueling Challenge: Strategy, Progress, and Stakes
Securing a tournament victory demands not only sharp poker skills but a bit of good fortune—winning 25 events in less than a month is a test of both. Sissman’s progress throughout December has been strong. As of December 12, he had clocked 13 wins, including a payout of more than $2,900 on PokerStars, and remained on track to meet his ambitious goal. To maximize his odds and allow for quality family time around Christmas, Sissman aims to stay ahead of schedule.
He is competing exclusively on New Jersey’s regulated platforms—sharing player pools with Michigan—as well as social gaming site Global Poker. The challenge features a mix of cash games and tournaments in No Limit Hold’em, Pot Limit Omaha (PLO), and PLO Hi/Lo, typically with buy-ins under $500. Sissman is also targeting online World Series of Poker Circuit events as part of his challenge.
While much of the feedback from fellow poker enthusiasts has been positive, Sissman admits the challenge does draw some criticism online. Despite occasional detractors, the overwhelming majority of supportive comments and likes on social media help keep him motivated.
Sissman notes, “The reaction has been like 90 percent positive, but some people freak out about it. I guess it’s just because it’s the Internet—people get mad. Honestly, the support and engagement from those following my progress really helps keep me going.”
Poker Journey: From Hobbyist to Professional
Sissman’s poker career began at an early age, learning the ropes at nine years old. His journey to professional status wasn’t planned. After graduating college in 2008 amid a struggling job market, Sissman turned his profitable hobby into a full-time commitment. He devoted 40 hours a week to online poker and, sixteen years later, continues to thrive in the game.
Alongside grinding online tournaments, Sissman spends his free time with his family, enjoying activities like hockey with his son and playing guitar. He also enjoys winding down with his wife for Saturday movie nights—though these sometimes take a back seat during the intense “25 Wins” grind.
He shares, “I’ll be working most Saturday nights during this challenge. I need every day I can get to have a shot at completing it.”
Expanding Horizons: Coaching, Content, and Giving Back
Looking beyond the end of the challenge, Sissman is planning to launch a new YouTube channel to offer free poker coaching, aiming to share the nuances and strategies behind his play to benefit beginner, intermediate, and even seasoned players.
“It’s been a dream of mine to start a free poker coaching channel, and I’ve already been working on it. I’ll be producing a lot of coaching videos. Beginners and intermediate players can learn a lot. Even experienced players might pick up something new,” says Sissman.
He also revealed he’s been recording all of his winning sessions for the “25 Wins of Christmas,” planning to turn those successes into instructional content for the channel. His goal: to upload all the challenge wins by the end of January.
It’s stormy outside and on the tables tonight in NJ.
Win #12 for the challenge and it’s a banger.
Wednesday Storm win on @PokerStarsUSA pic.twitter.com/PxlZ0nqruF— DeadMoneyJermz (@PokerJermz) December 12, 2024
The Final Stretch: Eyes on the Prize
With only a dozen more victories standing between Sissman and his 2024 goal, all eyes are on his progress as the finish line approaches. His journey highlights the dedication, skill, and resilience needed to stand out in the competitive online poker world.
From enthusiast to professional, and now educator, Jeremy Sissman’s “25 Wins of Christmas” reflects not just a personal feat, but a broader passion for the game—one he’s eager to share with a growing community.
