Steve Wolfson Jr. Continues Family Tradition With High Rollers Contest Win At Tampa Bay Downs

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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Tampa Bay Downs: High Rollers Handicapping Contest Set For Jan. 8

The annual High Rollers Handicapping Contest Presented by HorseTourneys is Saturday, Jan. 8,  at Tampa Bay Downs in Oldsmar, Fla., with first prize (based on 100 players) of $20,000. Players are required to deposit $1,000 to enter, with $500 serving as the player's bankroll for wagering and the remaining $500 going to the prize pool. At the conclusion of the tournament, any dollar amount remaining in the bankroll remains the property of the player.

Wager types permitted are win, place and show only, with each player making five $100 win, place and/or show bets during the tournament.

The player with the highest bankroll takes top prize (50 percent of the prize pool), plus a seat in either the 2022 or 2023 National Thoroughbred Racing Association National Handicapping Championship in Las Vegas, plus accommodations.

To enter, register at www.tampabaydowns.com and make the required $1,000 payment by noon Eastern on Jan. 8. For details, contact Margo Flynn at mjflynn@tampabaydowns.com or (813) 855-4401, extension 1368.

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Tampa Bay Downs, HorseTourneys Teaming Up For Jan 8 High Rollers Handicapping Contest

The annual High Rollers Handicapping Contest Presented by HorseTourneys is Jan. 8 at Tampa Bay Downs in Oldsmar, Fla., with first prize (based on 100 players) of $20,000. Players are required to deposit $1,000 to enter, with $500 serving as the player's bankroll for wagering and the remaining $500 going to the prize pool. At the conclusion of the tournament, any dollar amount remaining in the bankroll remains the property of the player.

Wager types permitted are win, place and show only, with each player making five $100 win, place and/or show bets during the tournament. The player with the highest bankroll takes top prize (50 percent of the prize pool), plus a seat in either the 2022 or 2023 National Thoroughbred Racing Association National Handicapping Championship in Las Vegas, plus accommodations.

To enter, register at www.tampabaydowns.com and make the required $1,000 payment by noon on Jan. 8. For details, contact Margo Flynn at mjflynn@tampabaydowns.com or (813) 855-4401, extension 1368.

Thoroughbred racing continues Sunday, Dec. 26, with a nine-race card beginning at 12:15 p.m. ET. Sunday is also the first day of the track's annual “Calendar Giveaway,” with the 2022 edition given away free to the first 5,000 patrons. The calendar features a variety of images certain to enhance fans' enjoyment of the track and the horses.

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Tampa Bay Downs: ‘Plan B’ Helps Chenvert Win High Rollers Contest

When he crunched the numbers for the last race of Saturday's High Rollers Handicapping Contest at Tampa Bay Downs in Oldsmar, Fla., Bill Chenvert determined 6-year-old mare Pugilist was the horse to beat in the one-mile claiming event on the turf.

Quick math also revealed Chenvert could not make enough money on the even-money favorite to win the contest. So he turned to his second choice, 4-year-old filly Caribbean Kitten, who had won her previous race and carried more generous odds of 9-2. After placing his contest wager of $100 to win, Chenvert, along with his son Brian and grandson Will, watched things unfold in the Skye Terrace Dining Room.

Pugilist moved first, but Caribbean Kitten was flying on the outside. Her 1 ¾-length victory from 12-1 shot Shes Dynomite added $570 to Chenvert's contest bankroll, giving him $2,090 and enabling him to edge past Greg Lewis by $30 for the top spot and first prize of $17,000.

Lewis won $6,800 for second. Both men also won seats in either of the next two National Thoroughbred Racing Association National Horseplayers Championship in Las Vegas. There were 83 entries in the High Rollers contest.

“We were making a little bit of noise in the restaurant” (during the last race), said Chenvert, a 70-year-old resident of The Villages in central Florida. “It's exciting when you win any tournament, but that was kind of an unbelievable finish. It's just a thrill when you compete against that quality of players.”

Success in the world of big-money Thoroughbred handicapping contests is nothing new for Chenvert. He finished second to Brian, his son, in last year's Pegasus World Cup Betting Championship at Gulfstream Park and was second in the 2019 Breeders' Cup Handicapping Tournament at Santa Anita. On top of that, he is competing this weekend in the Flo-Cal Faceoff and the HorsePlayers BCBC contest.

Chenvert, who owns a nursery and landscaping company in The Villages with his wife, said the High Rollers Handicapping Contest more than meets his competitive instincts. “Tampa Bay Downs is kind of close by, and I enjoy the track,” he said. “The contest is easy to enter and they do a good job running everything. We look forward to playing it again.”

Chenvert got off to a rip-roaring start, collecting $1,520 in contest cash on his first wager of the contest, a $100 bet on 14-1 shot Blueyed Princess in the fourth race on the turf. He chose the first-time starter based on her bullet five-furlong workout of 1:02 from the gate on New Year's Day at Classic Mile Training Center in Ocala.

Lewis, a Columbus, Ohio, resident who finished fifth in last year's High Rollers, also had $100 to win on Blueyed Princess (are these guys lucky or just dang good?). Lewis said the High Rollers Handicapping Contest – which required a $1,000 buy-in – is a great option for handicappers ambivalent about paying a five-figure entry fee to chase six-figure prizes.

“It's a good contest for the medium-to-small player,” Lewis said. “It's well-organized, you don't have to be a heavy player to have a shot and all the money goes back to the players. I'm extremely happy with what happened. I got more than I deserve.”

Finishing third with a final bankroll of $1,987.50 was John Kaiser of Krotz Springs, La. He earned $5,100. Fourth was Scott Prestridge of Euless, Texas, who finished with a bankroll of $1,750 to collect $3,400. Fifth was John Fisher of Leesburg, Fla., whose bankroll of $1,595 was worth $1,700.

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