Steve Wolfson, second from right, won the High Rollers Handicapping Contest. Others (left to right) are Evan Trommer (3rd place), Vincent Griffo (5th), John Kaiser (2nd), Mackey Smith of sponsor HorseTourneys, and Jose Giron (4th)
Steve Wolfson Jr., and his father, Steve Wolfson Sr., had one of those afternoons Saturday at Tampa Bay Downs that horseplayers file away in their memory banks for a lifetime.
The high school social studies teacher and the long-time horseman made the three-hour drive from Ormond Beach on Florida’s east coast to enjoy an afternoon of racing at Tampa Bay Downs in Oldsmar and, not coincidentally for Steve Jr., to compete in the High Rollers Handicapping Contest Presented by HorseTourneys.
“We haven’t traveled much the last couple of years because of COVID,” said the younger Wolfson, “so it was a chance enjoy great racing, and it was a glorious day to be outdoors. It never gets old, but it’s best when it’s shared.”
And by coming home with the top prize of $23,000, plus his final contest bankroll of $1,779.20, Wolfson Jr., couldn’t have had a more fulfilling day. “It was a wonderful time with the person who introduced me to racing,” he said. “It was a really good ride over, and better coming back.”
Both Wolfson Jr., and second-place finisher John Kaiser of Krotz Springs, La., qualified for the National Thoroughbred Racing Association/National Handicapping Championship from Jan. 28-30 at Bally’s Las Vegas. Kaiser’s final bankroll was $1,690, and he earned an additional $9,200 for finishing second (top-10 below).
Individuals who play handicapping contests are rarely lacking for confidence, but many in the field of 112 players with an appreciation for the challenge involved were respectful – if not fearful – of the Wolfson name. Steve Jr., and his dad, who did not compete, are members of the National Handicapping Championship (NHC) Hall of Fame.
Wolfson Jr., won the 2001 NHC Championship at Bally’s Las Vegas, collecting a cool $100,000, while his father finished fourth. In 2017 at Treasure Island in Las Vegas, the younger Wolfson finished second, earning $250,000.
Wolfson Sr., had put on some handicapping tournaments in the 1990s that were the forerunner of the NHC events, setting the standard for subsequent contests in terms of player hospitality and amenities. Wolfson, Jr., praised Saturday’s Tampa Bay Downs event as a first-class production, with all the intensity, camaraderie and ups and downs serious players thrive on.
“Whenever you bring people together like that, there is so much energy flowing that it’s tremendous fun. It’s just nice to have people there in person sharing the excitement and not at home behind their computers,” Wolfson Jr., said.
The High Rollers champion comes by his love of racing, and his knowledge of handicapping, through vast experience around Thoroughbreds. Wolfson Sr., and his brother, the late Gary Wolfson, were prominent Florida breeders and owners who owned 497-acre Happy Valley Farm in Marion County, and young Steve often traveled with them to major racetracks for big races throughout the country. Another uncle, Marty Wolfson, was a successful trainer from 1972-’18.
Going back another generation, Wolfson’s grandfather, the late Louis Wolfson, owned Harbor View Farm, which bred and owned 1978 Triple Crown winner and two-time Horse of the Year Affirmed. Young Steve attended the 1978 Kentucky Derby as a 10-year-old and the 1978 Belmont Stakes nine days after turning 11, wondering like so many others how the heck 18-year-old jockey Steve Cauthen did it.
“That was a wonderful introduction to the highs of horse racing. It has been in my blood a long time,” Wolfson said.
In Saturday’s contest, Wolfson displayed his bona fides in the fourth race, placing $100 of his bankroll to win on Dos Vaqueros. “It was such a weak condition (horses 4-years-old-and-upward who had never won two races, sprinting six furlongs for a claiming price of $8,000), and he showed a bullet workout and a five-furlong workout in (1:00 1/5). It seemed like that was enough,” Wolfson said.
It was, but hardly anyone else followed suit, both in the contest room and elsewhere. Dos Vaqueros, 5-1 on the morning line, paid $24 to win.
Wolfson managed his bankroll judiciously after that big score, and his $60 win wager in the ninth race on Cajun Casanova, who paid $5.80 to win, clinched the top position.
John Kaiser staged a whirlwind rally to finish second, hitting the last three races on the card at $100 to win a pop. He will be making his seventh appearance at the NTRA/NHC and hoping to cash big for the first time.
“I didn’t have that early long shot, so I had to stay patient,” Kaiser said. “I didn’t want to reach too far, and I was able to stay consistent.” He won four of his five wagers on the day, with his score on first-time starter In the Union, a Todd Pletcher-trained colt who paid $13.60 to win in the eighth race, fueling his comeback.
“The atmosphere was excellent and having HorseTourneys step up to sponsor the tournament was really nice,” Kaiser said. “I really enjoyed it, and the people who ran the contest did a great job.”
Here are the top-10 finishers, along with their final bankroll figures and additional earnings in parentheses:
Steve Wolfson, Jr., $1,779.20 ($23,000); John Kaiser, $1,690 ($9,200); Evan Trommer, $1,590 ($6,900); Jose Giron, $1,356 ($4,600); H. Vincent Griffo, $1,200 ($2,300); Edward Enbong, $1,180; Andy Muhlada, $1,145; Brody Wolfgram, $1,070; Andrew Hennosy, $1,010; Henry Gruss, $1,000.
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