The Special’s Halloran wins Keeneland’s Grade One Gamble

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Paul Halloran (center) and other top finishers at last weekend’s Grade One Gamble handicapping contest at Keeneland.

Paul Halloran made his first trip to the Lexington area last week to work on a book project. He did that, and so much more.

Halloran, a lead correspondent for The Saratoga Special and This Is Horse Racing since 2019, took in the scene at Keeneland Race Course, visited personal favorites Catholic Boy and Curlin, noshed on a steak at Tony’s and beat out nearly 300 other horseplayers to take down one of the country’s most prestigious handicapping contests. Halloran topped a record field of 292 to win first prize of $73,000 in Keeneland’s Grade One Gamble contest, earning spots in the 2023 Breeders’ Cup Betting Challenge at Santa Anita Park and the 2024 NTRA National Horseplayers Championship in Las Vegas. 

“I’m sure there are people looking at the final leaderboard wondering who the hell is this Halloran guy, and you couldn’t blame them. I’ve played a decent number of smaller contests, mainly the Saturday $300 NYRA contests and the Sunday Low Roller at Saratoga,” Halloran said. “I made a last-minute decision to enter the Keeneland contest Saturday and everything just came together.”

The Grade One Gamble featured players participating onsite at Keeneland and throughout the U.S. and Canada on XpressBet, TVG, 4NJBets, NYRABets and HPI.  The event featured a $3,500 entry fee with $2,500 going toward a live bankroll and $1,000 to the prize fund. Players were required to wager a minimum of $400 in at least five races at Keeneland.

Halloran, a resident of Lynn, Massachusetts, finished the event with a final bankroll of $60,105. A majority of that haul came from his $10,000 late daily double wager on odds-on favorite In Italian in the Grade 1 Jenny Wiley Stakes and 5-2 favorite Tarabi in the finale, yielding winnings of $59,900. He finished more than $22,000 ahead of runner-up Drew Coatney of Columbus, Ohio.

“The strategy going in was to play a big double with In Italian into Tarabi in the last race,” Halloran said. “After hitting the double ending in the Lexington, I was in position to play three doubles starting in the 10th, and put more than originally planned on the 2-12. In Italian romped, and Tarabi was getting caught, but held on by a neck. That was the difference between winning and finishing with nothing.

“I can’t say I had any clever opinions. The highest odds of the horses I cashed on was 5-2. It was just a matter of being willing to bet amounts that I am certainly not accustomed to betting on a regular day at the races. I had a plan and stuck to it and everything fell into place.”

Paul Halloran visited with Cody Dorman, namesake of multiple Grade 1 winner Cody’s Wish, last weekend in Kentucky.

Halloran’s trip to Keeneland came on the heels of visiting Cody Dorman, the courageous young man who was the inspiration of 2022 Breeders’ Cup Dirt Mile winner Cody’s Wish, and his family. Halloran earned an Eclipse Award honorable mention for his story about Cody’s Wish and Cody Dorman that appeared in the August 31, 2022 edition of The Saratoga Special and he’s working on a book about the pair.

“The contest win is obviously a career gambling highlight, but it was far from the highlight of the weekend,” Halloran said. “Meeting Cody Dorman and his family in person for the first time and spending a lot of time with them was absolutely the best thing that happened to me last weekend. I covered a lot of ground with interviews for the book I am working on, so all in all it could not have been a better weekend.”

After visiting with the Dormans he came to Keeneland with Howard Kravets, friend and cohost of the HHH Racing Podcast. 

“I had a seat in the room the contest was being held (Phoenix Room) and had friends who were playing, so I decided to hop in,” said Halloran, whose entry in Turf writing was covering Diggin Ditches’ victory in the 1985 Suffolk Downs Spring Handicap at his home track. “I had no strong opinions in the first half of the card and only bet one of the first five races in the contest, and lost. Barber Road – ridden by Reylu Gutierrez, whom I have written about for The Special a few times – was my play of the day, so I used him in big daily doubles and placed a large win bet on him. If he lost (he won by a neck), I would have been out of the contest with four races left on the card.”