Drew Wynkoop

Christopher Wynkoop, a real estate broker from Indianapolis, Indiana, began his poker journey playing low-stakes cash games at local clubs. In 2019, he entered a $150 single-table satellite at the Speedway American Legion charity poker club, winning entry to a second satellite which he also won, securing a seat in the WSOP Main Event along with $2,000 for expenses.

The 2019 WSOP Main Event marked Wynkoop's first time playing the tournament. Starting from Day 1C, he accumulated chips steadily, reaching a peak as chip leader on Day 4 after a pivotal hand where he held a pair of eights against Thomas Drinkwater's Kx8x on a Kx8x6x flop. He finished Day 4 ninth in chips and continued to advance through Day 5 with aggressive plays, including a successful all-in bluff with J♠9♠ on a busted flush draw and a six-high semi-bluff against Kevin Rand. Wynkoop ultimately finished 48th out of 8,569 players, earning $173,015—his largest live cash to date.

Wynkoop has recorded several other cashes in major events. In 2014, he finished 8th in a WSOP Circuit event at Horseshoe Hammond for $12,042. He cashed in the 2024 WSOP Event #20: $300 Gladiators of Poker, finishing 523rd for $1,420. More recently, in May 2025, he placed 178th in the MSPT Main Event at FireKeepers Casino for $3,387. According to WSOP.com, his total live earnings stand at $189,864, while The Hendon Mob lists $193,125.

Wynkoop's typical game is $1/$3 no-limit hold'em, occasionally moving up to $2/$5. He describes his Main Event run as "surreal" and credits the support of the Speedway American Legion poker community. His style is aggressive and adaptable, as demonstrated by his willingness to bluff and apply pressure in deep-stacked situations. Despite limited experience in high-stakes tournaments, he has shown an ability to compete against top players.