After Just Five Years of Playing the Horses, Riley Drexler, 27, Achieves Life-Changing Victory in the Players Championship at HorseTourneys

High-stress, big-money tournaments are not normally Riley Drexler’s milieu.

“Seeing so many impressive names on the leaderboard…” the Chicago resident said, his voice trailing off. “To say I was nervous would be an understatement.”

As a 27-year-old working in sales for a carrot and fruit-beverage company, paying the $2,000 entry fee for the $451,780 Players Championship on April 9-10 at HorseTourneys was never an option for Drexler. However, he won his way into the event via a $118 qualifier in March.

“It was a full-card Gulfstream contest, and it was chalky,” Drexler recalled. “I only had one winner, but it was an 18-1 shot on the synthetic, and it was ridden by Leonel Reyes. I wouldn’t be here if it wasn’t for him. I guess I owe him a drink.”

Maybe a couple of drinks. 

After two days of consistently fine play, Drexler, playing just one entry against many of the best handicappers in the country, finished first in the 253-entry contest and earned the grand prize of $161,212.

“The feeling is unmatched,” Drexler said. “It reminds you why you got into the game.”

Of course, in Drexler’s case, the decision to start playing the horses really wasn’t that long ago. It happened in 2017, when he was still studying—and playing football—at Grinnell College, a small, liberal arts school in Iowa with a very well regarded academic reputation. He started out mainly just playing the races on big days, but got more serious a couple of years later, following horse racing people on Twitter and reading as many racing books and listening to as many podcasts as time would permit. In 2020, he opened up his first account at HorseTourneys.

“It’s a very fun website. I recommend it to my friends a lot. I grew up in South Florida and so I really like the $12 Gulfstream tourneys. I play in those and just have a blast. It’s a good way to be engaged in the sport.”

Drexler did once finish just 10 cents shy of qualifying for the 2020 Breeders’ Cup Betting Challenge at HorsePlayers. And he once hit a Gulfstream Pick 4 for $10,000 on just a $24 ticket. More often than not, though, he can be found—just as he said—playing not for big stakes, but in those $12 cash games at HorseTourneys.

Which makes his performance in the Players Championship all the more impressive. Here were his plays on Day 1:

And here’s what he did on Day 2:

Many in the contest world believe that to conquer a lucrative handicapping contest, you need to really smoke out whatever bombs are out there, you need to be able to weather the inevitable dry spells within the game…and, strategically, you need to save a bunch of picks for the end of the tournament. Drexler did none of those things.

Drexler never went more than three plays without adding to his total. He didn’t have the one cap horse over the two days — 76-1 winner Power Surge in the final race of Day 1. And he left himself but one play for the final three races on Sunday. In fact, he never went longer than three contest races without making one of his requisite 15 plays per day.

“I definitely wanted to get some plays in early,” he said. “I’ve done well at the Big A during their winter meet, and I saw a couple of opportunities there. But I also didn’t want to be in a position of sitting on a bunch of picks and having to play races later where I didn’t like anything. I just went with what I liked.”

It won’t make the headlines, but Drexler believe a key moment in his eventual victory came towards the tail end of Saturday play when his score had him in contention for Day 1 bonus money if he could land something big with his final two selections.

“Instead I took the long approach and played two Santa Anita horses I really liked, even though I knew they wouldn’t get me any day money. I wound up getting $25 in those last two picks on Day 1, and that put me in a really good spot for Day 2.”

 Indeed. Buoyed by his unobtrusive late rally, Drexler finished Saturday in 7th place.

After missing with his first three plays on Sunday, Drexler went on another, under-the-radar mini-run that was both unspectacular, and highly effective.

“In the 4th at Aqueduct, I hit a Jose Gomez/Rudy Rod horse at 2-1 that got me on the board. Then at Keeneland, I had a Larry Rivelli horse…he’s a Chicago guy! Then right afterward I played a George Weaver/Cancel horse that got me almost $15. I think no one played that race because there was a 3-5 chalk in it. That race moved me from 5th to 2nd, and it might have been the first time the leader felt any pressure. 

About an hour later, Drexler came up with 6-1 winner Empress Ellie in Gulfstream’s 7th, and he found himself in a dogfight with Steven Meier who also had Empress Ellie, and was now leading Drexler by less than a dollar.

With four contest races, and just two picks remaining, Drexler was able to wrest the lead away from Meier.

“I jumped him with Lunatic in the 7th at Santa Anita,” Drexler recounted. “Now I said to myself, ‘Let’s just pray for chalk and get to the last race.’”

Prayer answered and then some.

Not only did 7-5 and 5-2 shots take the next two races, Meier spent his final two plays unsuccessfully in those two events. Drexler’s lead was now effectively up to $13.40 — over Michael Solakis, his nearest pursuer among those still with a play left. 

Despite the unfortunate turn of events for Meier, Drexler was fully impressed by his approach.

“I thought it was a good move,” Drexler commented. “He went for the win. If the roles had been reversed and I had not had the lead, I would have played something too…to zig when everyone was zagging.”

Drexler knew he would be unbeatable now if the Santa Anita race 10 favorite, Barrister’s Ride, won. So he opted to “get equity,” as he put it, with a second horse, 9-2 second choice She’s a Bit Sassy. Solakis went with 8-1 first-time starter Big Attraction. When neither hit the board, and Barrister’s Ride got up late, Drexler was suddenly $161,000 richer.

“It’s a race I’ll never forget—even though I didn’t pick the winner—and it was such a special feeling to win. For me, it validated a lot of the work I’ve put in over the last few years. Maybe I didn’t have the experience that most of the others had, but the result made me believe that I can do this too…and that I SHOULD be doing this. I do feel that the game can appeal to a younger generation, and I’d love to be in the forefront of that.”

To be sure, $161,000 is a lot of money to anyone, and especially to a 27-year-old. So what will Riley Drexler do with his winnings? His answer to that question was immediate.

“Well..I’ve got a couple of student loans that will be wiped. That’s a really good feeling.”

Beyond that, Drexler envisions taking a nice trip to South America at some point with his girlfriend Haley. Perhaps he’ll step up his efforts to qualify for his first BCBC or NHC or Keeneland Grade One Gamble.

“It’s life-changing money, but I don’t want to get too crazy,” he chuckled. “I’m still saving up, trying to find a place. I’ll keep playing at HorseTourneys, though.

“And I’ll definitely have a seat in the Spa & Surf Showdown,” he laughed. “Most definitely!”