Winning even when I’m losing

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The clouds filled the sky in Arcadia, but it was far from a gloomy time at the Great Race Place.

The Santa Anita Preakness Challenge gave some of the best horseplayers across the country an opportunity to strut their stuff. A live-money tournament with a $3,000 bankroll, the contest added even more flavor to a sensational weekend of racing.

This would be my second trip to the scenic Southern California racetrack. I also participated in a handicapping tournament there in March, but things spiraled out of control and I walked away without a dime to show for it.

New tournament. New life. That’s what I kept telling myself as I prepared to go up against the sharpest horseplayers in the game. With my maiden voyage to Santa Anita under my belt, I was much more relaxed walking through the turnstiles this time around.

It also helped that I saw some familiar people that I once considered strangers now my friends. The camaraderie among handicappers is one of the main reasons I love the contest world. 

Jonathon Kinchen agrees.

“Before I started to play in tournaments, I only had a couple friends in racing,” he said. “Now there are 20 to 30 people I’m really close with, and I owe it all to being a part of the contest scene.”

The 32-year-old from Austin, Texas, is currently second on the National Handicapping Championship Tour.

The first day of the tournament went by, and I gave back a little bit of my original bankroll. However, I still had enough left for Sunday’s card to jump up the leaderboard if I could make good on any of my opinions.

Beyond my normal handicapping of the card, I had to get ready for my first taste of working on-air in horse racing. Santa Anita’s VIP Player Concierge Tom Quigley invited me to be the guest on his seminar show, and I had the privilege of broadcasting my top selections to the masses.

I’d be lying if I said I wasn’t a little nervous, but Tom was a pleasure to work with and the show was done before I knew it. I kept track of how my picks panned out, and I ended up with three winners, including a $60 exacta. I hope someone held the winning tickets.

Before I knew it, the horses were loading in the gate for Sunday’s finale. The horse I touted was sitting on the board at an enticing 17-1 price.

I pulled the trigger at the windows. If the horse won, there was a chance I win the whole tournament.

Sleepwalker made a decent move around the far turn, but couldn’t keep up with some of the others in the stretch and faded to finish toward the back of the pack.

Swing and a miss.

Despite holding a losing ticket after the last race, I still felt like a winner.

From hanging out with Jonathon and a few other friends, to being a part of the handicapping show with Tom, I’m grateful for all of the opportunities through my involvement in tournaments.

It’s been about a year since I dipped my toes in the contest waters, and I don’t plan on getting out anytime soon.

Billy Blake is an associate producer at WNYT NewsChannel 13 in Albany, N.Y., and news and sports reporter for iHeart Radio. At the age of 23 earlier this year he was one of the youngest contestants in the NTRA/Daily Racing Form National Handicapping Championship at Treasure Island in Las Vegas. Read more about Billy from America’s Best Racing.


More about the Santa Anita Preakness Challenge from Daily Racing Form.