Sara Hess was a “horse-obsessed kid” from the time her grandfather put her on a pony before she could walk. She wanted to become a jockey after a rider gave her a pair of goggles in the Timonium Fairgrounds winner’s circle in Maryland when she was 4 or 5.
Despite achieving her ambition, the 26-year-old apprentice goes through times when she is plagued by self-doubt. She has always been comfortable on horseback, but adjusting to the rough-and-tumble world of the racetrack, she has discovered, requires much more than the 526 races she has ridden since beginning her career in November of 2021 at Laurel.
“There have been many times when I’ve thought to myself, ‘What am I doing?’ I know I can ride a horse, but am I going to have the skill set to do this (for a career)?” said Hess, whose career total of 39 winners leaves her one shy of becoming a journeywoman and losing her 7-pound apprentice weight allowance.
“There are things I need to work on. I want to clean up my riding a lot and focus on riding smart races and being as strong of a rider as I can. I’m putting my all into it, so I’m proud of myself in that aspect,” Hess said. “But there are things I need to get better at. I practice on the Equicizer (mechanical horse) and I pick myself apart on replays, but I’m still working on transferring everything I’ve learned to my races.”
For now, Hess has come far enough to earn the Mother’s Restaurant Jockey of the Month Award, climbing into 11th in the Tampa Bay Downs standings with 19 winners. And if desire and a willingness to learn from her mistakes count, the likelihood of Hess sticking around appears high.
“She’s a worker. I’ve never seen her miss a day,” said trainer Dennis Ward, a former jockey and the father of 1984 Eclipse Award Outstanding Apprentice (now top trainer) Wesley Ward.
Ward has teamed with Hess for a pair of allowance victories, two seconds and a third in the Lightning City Stakes on the turf with his 8-year-old Florida-bred mare, Bahamian Moon.
“Sara has a real good attitude, and riding a lot of horses doesn’t tire her out. She knows she has a lot to learn, but she pays attention and she’s learning quick.
“She can get them to break well, then settle back two or three lengths and sit cool. Pretty soon, they take off for her,” Ward said. “She is very confident and very competent, and the weight (allowance) doesn’t mean anything to me. It’s who is riding your horse and how they fit it.”
Other trainers whom Hess has made a strong connection with include Alejandro Olais Mendieta and Aldana Spieth.
“I like her hands and her demeanor on a horse,” said Spieth, the wife of veteran jockey Scott Spieth. “She comes to my barn with a really good attitude, and she likes to try to get to know each horse she rides for me. She is learning a lot every day, and if something doesn’t go the way it’s supposed to one time, she’ll make a suggestion about trying something different.
“She wants to do things the right way, and she listens. You don’t always find that with some of the younger riders,” Spieth added.
Hess began working in earnest toward being a jockey when she was 14, going to work for well-known Maryland horsewoman Ann Merryman. “I walked horses, rubbed horses and learned how to break babies at her farm, and when I was 17 and she felt I was mature enough, she took me to the racetrack with some 2-year-olds I helped break and taught me how to gallop,” Hess said.
“I can still hear her voice in the back of my head when I get on a naughty one out there – ‘Do this’ or ‘do that!’ ”
Along the way, Hess came to understand that her best chance of achieving her dream of competing on the racetrack rests with immersing herself totally in the lifestyle. Being around horses all the time was a dream come true, but finding the means to support herself required nothing less than 100-percent commitment.
“I’m really good on horses in the mornings. Before I got my license, I’d been breezing and galloping racehorses for years. But that’s nothing compared to racing,” Hess said. “Just because you can break one out of the gate and breeze 5/8s in the morning does not mean you are ready to ride races.
“I didn’t really have anybody to guide me at the beginning, which is why I had a very slow start to my career,” said Hess, who does not currently employ an agent. “I had to figure out a lot of stuff on my own, so I absorbed as much information from as many people as I could and figured out what would work best for me.”
After riding one race in 2021, Hess rode primarily in Maryland the following year, then branched out to Turfway Park in Kentucky and Belterra Park in Ohio in 2023. On May 12 of that year at Belterra, in her 54th career race, she scored her first victory on Endless, a (then)-4-year-old filly owned in partnership by her close friend Janey Adams and trained by Nancy Adams, Janey’s mother. The following winter, Hess rode Endless to a pair of victories at Turfway Park in Kentucky.
Hess has competed at 15 tracks, including a scattering of mounts at Churchill Downs, Keeneland and Gulfstream Park. Based on her experiences this season coming to Tampa Bay Downs from the Ohio and Kentucky circuits, her concerns about “making it” in the business continue to lessen.
“I really didn’t have many expectations when I came here – just to get more opportunities, ride more horses and maybe some better horses, make more connections and get more experience,” she said. “It’s turned out better than I could have thought. There have been so many trainers here who have given me amazing opportunities.
“Knowing that trainers like Dennis Ward have that kind of confidence in me makes me feel I have the confidence and ability to do it. I know I just have to stay positive, because tomorrow you could have the best racing day of your life.”
Hess feels good about crafting a few candidates for “best racing day ever” at the Oldsmar oval. There was Bahamian Moon’s third-place finish on Feb. 22 in the Lightning City at odds of 28-1 (the jockey’s first-ever stakes mount), and their subsequent victory against males on March 15 in an allowance/optional claiming race.
Hess has also ridden two winners on a single card here three times. For pure joy, it would be hard to top March 7, when she rode a pair of winners for trainer Arnoud Dobber with her mother Mia Hess, her grandmother Sondra Hess and her kid brother Jack visiting from Maryland.
“Jack just turned 11, and we took him to Universal Studios for an ‘early’ birthday present and had a fantastic time,” Sara said. “Then to have them come to the races and see me win twice – it was the first time Jack got to see me ride, so that was super cool.’ ”
After the current meet, Hess plans to compete at Belterra Park and Horseshoe Indianapolis, perhaps getting to Ellis Park or maybe Churchill later in the summer. She is eager to find what awaits her in this exciting journey she shares on a daily basis with her Australian Shepherd Rocky, her orange cat Cheeto and the racetrack community.
Plus her friends the horses, whom she feels as close to as she dreamed when she first rode a pony and received a pair of goggles.
“Things were not always great when I was young, and the horses were always the one constant in my life. I was able to get on my pony and run off into the woods when I needed to get away,” she said.
“I do this for the love of the horses. That is the whole point of the sport, to me. People can lose sight of that because it’s so tough to survive (financially) in this industry. But none of this happens if we don’t have that love for the animal and the sport, and for me there is no better feeling than putting my all into it.”
Around the oval. Leading jockey Samuel Marin rode two winners today, giving him 90 for the meet. He won the second race on Utopia Rose, a 4-year-old filly owned by Akamai Racing Stables and trained by Chelsey Moysey. Marin added the fifth on the turf aboard Miss Taptress, a 4-year-old filly owned by Frank D’Amato and trained by Gregg Sacco. Miss Taptress was claimed from the race for $16,000 by trainer Gerald Bennett for his Winning Stables.
Trainer Michael Yates each sent out two winners. O’Connell won the first with 5-year-old mare One Violent Affair, He captured the fourth race with Bohemian Style, a 3-year-old Florida-bred gelding owned by Stonehedge, LLC and ridden by Sonny Leon. Bohemian Style was claimed from the race for $16,000 by new owner-trainer Juan Arriagada.
Yates also won the sixth with 3-year-old Florida-bred colt Forthelonghaul, owned by the conditioner’s Shadybrook Farm and ridden by Marcos Meneses. Forthelonghaul was claimed for $25,000 by trainer Jon Arnett for new owner Charles D. Nielsen.
Defending Florida Cup ESMARK Turf Classic champ Forever Souper is the 2-1 morning-line favorite for Sunday’s $110,000 renewal, one of 11 races, including six Florida Cup Day stakes, on the 11-race card. Post time for the first race is noon and the ESMARK Turf Classic, which is the eighth race, should go off around 3:48 p.m. There are 12 entered.
All of the Florida Cup races are for registered Florida-breds.
Forever Souper, a 6-year-old gelding bred and owned by Live Oak, is trained by Michael Trombetta and will be ridden in the mile-and-an-eighth grass event by Paco Lopez, his first assignment on Forever Souper since last year’s ESMARK Turf Classic.
The first Florida Cup race Sunday is the fourth, the Ocala Breeders’ Sales Sophomore for 3-year-olds at 7 furlongs on the main track. The 1-2 morning-line favorite in the seven-horse field is Macho Music, owned by Rohan Crichton, Mark Fletcher Taylor and Daniel L. Walters and trained by Crichton. Javier Castellano is the jockey.
The seventh race, the 7-furlong Stonehedge Farm South Sophomore Fillies, is headed by 3-1 morning-line favorite Bella Cleopatra. Castellano will be aboard for owners Black Type Thoroughbreds, Swinbank Stables, Steve Adkisson and Campeche Stables and trainer George Weaver. There are eight entered.
Dancing N Dixie is the 5-2 morning-line favorite in a 12-horse field for the Pleasant Acres Stallions Distaff Turf, the ninth race Sunday at a mile-and-a-sixteenth on the grass. Owned by Gary Barber, Rocky Top Stable and LEMB Stables and trained by Mark Casse, the 4-year-old filly will be ridden by Dylan Davis.
The 10th race is the 6-furlong NYRABETS Sprint for horses 4-years-old-and-upward on the main track. The 5-2 morning-line favorite in the 10-horse field is Comedy Town, owned by Ten Twenty Racing and Saffie A. Joseph, Jr., and trained by Joseph. The jockey is Edgard Zayas.
Rounding out Florida Cup Day is the 11th race, the Equistaff Sophomore Turf for 3-year-olds at a mile-and-a-sixteenth. The morning line shows Tank, a colt bred and owned by Arindel and trainer by Carlos David, at 3-1 in the 10-horse field with Luis Saez in the irons.
Thoroughbred racing at Tampa Bay Downs continues Saturday with a nine-race card beginning at 12:15 p.m. Two “Road to the Kentucky Derby” prep races, the Grade I, $1-million Curlin Florida Derby from Gulfstream Park and the Grade I, $1-5-million Arkansas Derby from Oaklawn Park, will be simulcast, with post time for the Curlin Florida Derby at 6:42 p.m., and post time for the Arkansas Derby at 7:48 p.m. (Eastern Time).
Tampa Bay Downs races Wednesdays, Fridays, Saturdays and Sundays and is open every day except April 20, Easter, for simulcast wagering, no-limits action and tournament play in The Silks Poker Room and golf fun and instruction at The Downs Golf Practice Facility.
