With many poker players shuttered at home due to Covid-19 lockdowns, poker fans might think there would be a shortage of the prop bets and grudge matches to keep the game interesting. One poker player is back in the spotlight after one of his previous challenges resurfaced online and garnered interest from a few well-known betters. Mike “Timex” McDonald has already successfully completed a number of bets people thought impossible but the most recent one has many questioning if he has finally pushed it too far as he seeks to become a Chess Grandmaster.

Prop bets are a Vegas and gambling tradition and are often made on the sidelines of a poker game. Some of these will be settled on the felt, either a typical side bet between two players on the colour of the next flop or something more personal like the case of the Negreanu-Polk High Stakes Feud currently ongoing.

Others though may have nothing to do with poker, or any card game, at all. Phil Hellmuth famously pledged to shave his head at the 2002 WSOP after if the player who eliminated him, Robert Varkonyi, went on to win. Amateur poker player Varkonyi ended up with the bracelet and Hellmuth ended up bald. Amongst these types of prop bettors though, McDonald stands out as one who frequently takes on the near impossible.

Netflix series inspires most recent challenge

The Queen’s Gambit has taken the world by storm showcasing the inspiring tale of an orphaned teenage girl battle both addiction and the best chess players around the globe. Along with the popularity of the Netflix series, there has been a resurgence in people trying out the classic strategy game. This led to American poker pro, Dan Smith, musing on Twitter about an old prop bet challenge from McDonald.

McDonald hails from Waterloo, Canada and began crushing the poker world as a teenager and has racked up over $13 million in career tournament winnings. Not content with mastering the poker world alone, he’s dipped his feet into a variety of other fields, including founding the Pokershares website which allows players to bet on any poker player.

Prop betting is an area McDonald seldom backs down from and he was quick to respond to Fedor Holz’s question on what the stakes would be. McDonald agreed he would take on the challenge of becoming a Grandmaster of chess within his lifetime – at a minimum of his $400,000 against a potential $4 million payday.

Becoming a chess Grandmaster requires a player to achieve a score of 2500 under ELO (the ranking system for chess players). Only one player, Davorin Komljenovic, has ever managed to achieve the title of Grandmaster when starting their quest above the age of 30. Conventional wisdom would make the bet against McDonald an easy win yet so far though, no one appears to have stepped up to the plate.

Basketball another hidden McDonald talent

It’s not just chess though that McDonald has taken a prop bet on. Back in April of this year, he took on a $100,000 prop bet which required him to shoot 90 out of 100 free throw attempts. While he did have some basketball experience, shooting 90% from the free throw line is something only accomplished on a career basis. McDonald would need to join the likes of Stephen Curry, Steve Nash, and Mark Price to take down the prize.

He ended up not even needing the full year and cleaned up on that in early September with the evidence in the video below.

Come back to YourPokerDream regularly as we provide updates on whether Timex finds enough action to go ahead with his chess quest, as well as, keeping you up to date on Negreanu-Polk heads-up battle.



Hi Guys! I am Marc Kitch and one of the Content Managers at YourPoker Dream. As a recreational poker player for over a decade, I’ll bring you the latest in news, views and general advice from the world of online and live poker.

· Published 27.11.2020 · last updated 14.01.2021