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Betting Highlights
Favorite Bet of All-Time
I grew up with the great David "Chip" Reese as a mentor. Many in the poker world consider Chip the greatest cash-game player in history because of his ability to play his A-game when any amount of money was on the line. My favorite gambling memory doesn't stem from pure monetary value. Instead, it comes from the first bet I ever placed when I was only five or six years old. My family flew up with Chip on his private jet to stay in his Montana home. His son, Casey, made a wager that I couldn't eat an entire plate of marshmallows one night around the campfire. One thing led to the next (most notably me puking in the backwoods), although a winning bet was made on my part that night when 50-pound me devoured the entire plate and caused Casey to run to Chip to retrieve 20 dollars. Who else can say they won their first bet and got paid out by the greatest poker player ever?
Most Heartbreaking Bet
2018 Kentucky Derby — Nine months before the Kentucky Derby, I placed multiple futures wagers on Mendelssohn at 150/1 to win what would have been my most significant amount ever. Let's just say it was large. Mendelssohn ended up closing as the second-favorite behind Justify when the race came around in May. Bumped out of the gate and slop thrown in his face resulted in a heart-breaking last-place finish —the high of highs before the race to the low of lows.