by Mike Henry

Steve Wolfson, Jr., and his father, Steve Wolfson, Sr., had one of those afternoons Saturday that horseplayers file away in their memory banks for a lifetime.

The high school social studies teacher and the long-time horseman made the 3-hour drive from Ormond Beach on Florida’s east coast to enjoy an afternoon of racing at Tampa Bay Downs 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.”


Saturday's High Rollers Handicapping Contest Presented by HorseTourneys winners included, from left to right: Evan Trommer, 3rd place; Vincent Griffo, 5th; John Kaiser, 2nd; sponsor Mackay Smith, HorseTourneys; Steve Wolfson, Jr., champion; and Jose Giron, 4th; Wolfson and Kaiser are headed to Las Vegas

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 1972-2018.

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 6 furlongs for a claiming price of $8,000), and he showed a bullet workout and a 5-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.

Make way for the sophomores. Saturday’s Skyway Festival Day card includes three stakes races, highlighted by a pair of $125,000, 7-furlong events for 3-year-olds: the Pasco Stakes for males and the Gasparilla Stakes for fillies. The third stakes on the card is the $50,000 Wayward Lass Stakes, for fillies and mares 4-years-old-and-upward going a mile-and-a-sixteenth.

The expected entrants for the Pasco include Corinne Heiligbrodt, William L. Heiligbrodt and Spendthrift Farm’s colt Cattin, who won the 6-furlong Inaugural Stakes here on Dec. 4, and Granpollo Stable and Ricardo R. Vallejo’s colt Grand Valley, who finished third in the Inaugural. Also likely are Provocateur, who broke his maiden here on Dec. 23, and Cyberviking, a winner of three of his four career starts.

The top three finishers from the 6-furlong Sandpiper Stakes on Dec. 4 are expected to return in the Gasparilla: winner Strategic Bird, owned by Gary Barber; runner-up Devine Charger, owned by J D Farms; and third-place finisher Chasing Happiness, owned by William A. T. Rainbow. Another possible starter is LNJ Foxwoods’ filly Outfoxed, a Bill Mott-trainee who won back-to-back Florida Thoroughbred Breeders’ and Owners’ Association stakes last year at Gulfstream.

In the Wayward Lass, the 4-year-old filly Allworthy – owned by Slam Dunk Racing, Saffie Joseph, Jr., Daniel Damen, Dominique Damico, Steven Bouchey, Parkinson Goodrich, LLC, K-Mac Stables, LLC and Brian Martin – looms as a serious threat, should she start. Her last four races have been in stakes company, with third-place finishes in the Grade III Charles Town Oaks on Aug. 27 and the Rampart Stakes at Gulfstream on Dec. 18.

Around the oval. In today’s third race, the $31,000 Pelican Prep, 7-year-old horse Mr. Jagermeister overpowered five rivals, drawing off to a 7-length victory under jockey David Cardoso. About Today finished second and Awesome Anywhere was third.

Mr. Jagermeister extended his career record to 13-for-37 while raising his lifetime earnings to $700,839, the most of any Minnesota-bred horse. His time for the 6-furlong distance was 1:08.95, .28 seconds off It’s Me Mom’s 2012 track record.

Trainer Valorie Lund, who owns Mr. Jagermeister with her sister, breeder Kristin Boice, said he is likely to return for the $100,000 Pelican Stakes on Feb. 12. Mr. Jagermmeister has won seven stakes races at Canterbury Park in Minnesota and one at both Colonial Downs in Virginia and Turf Paradise in Arizona.

Cardoso also rode the winner of the seventh race, 5-year-old Florida-bred mare Smooth as Glass, for owner Juvenal Sanchez and trainer Angel M. Rodriguez.

Pablo Morales rode three winners today, giving him eight this weekend. Morales won both halves of the early daily double, capturing the first race on Jack Rabbit Quick, a 4-year-old Florida-bred gelding bred and owned by Endsley Oaks Farm and trained by Rafael Schistl. Morales added the second race aboard Lucky Lover Boy, a 7-year-old gelding owned by Averill Racing and trained by Gerald Bennett. Lucky Lover Boy was claimed from the race for $5,000 by trainer Douglas Nunn for new owner Winner Circle Stables.

Morales added the eighth race on the turf, the Cody’s Original Roadhouse Race of the Week, with Pharaoh’s Prophecy, a 3-year-old colt owned by Chester A. Bishop and trained by Michael Maker. Morales leads the Oldsmar jockey standings with 26 winners.

Wilmer Garcia rode back-to-back winners today. He won the fourth race with U Know I B Lion, a 6-year-old mare owned by Jill Ciperski and trained by Victor Russo. Garcia added the fifth on Spanish Delight, a 4-year-old filly bred in Florida by her owner, Carlos Giraldo, and trained by Mario Lorito.

Thoroughbred racing continues Wednesday with a nine-race card beginning at 12:20 p.m. Tampa Bay Downs races on a Wednesday-Friday-Saturday-Sunday schedule, with the exception of Easter Sunday, April 17, when the track is closed.

Otherwise, the Oldsmar oval is open every day for simulcast wagering, no-limits poker action and tournament play in The Silks Poker Room and golf fun and instruction at The Downs Golf Practice Facility.