At 29 years old, Tyler Gaffalione is among the most sought-after jockeys in the racing business by owners and trainers.
If he wins Saturday’s $5-million Kentucky Derby presented by Woodford Reserve, he may learn what it’s like to be in demand among a much wider audience.
The personable star, whose winning smile is imprinted in the minds of many of his fans, will ride Sierra Leone, one of the favorites for the 150th Run for the Roses at Churchill Downs. They have won two races on the Triple Crown trail: the Grade II Risen Star Stakes on Feb. 17 at Fair Grounds and the Grade I Toyota Blue Grass on April 6 at Keeneland.
The race will be simulcast at Tampa Bay Downs at 6:57 p.m., after the conclusion of the Oldsmar oval’s season-ending 10-race card. Advance wagering on the race will be available Friday and Saturday.
Tampa Bay Downs, which has hosted three Kentucky Derby winner since 2007, will roll out many of the race’s trademark traditions throughout the day, with an emphasis on fashion, food and the traditional Kentucky Derby drink – a mint julep – in souvenir glasses listing the race’s 149 previous winners.
Gaffalione and Sierra Leone, who is trained by Chad Brown, are slated to break from the No. 2 post position against 19 other potential legendary 3-year-olds. Their morning-line odds are 3-1, behind only Fierceness and John Velazquez at 5-2.
A 2013 graduate of Sunlake High School in nearby Land O’ Lakes, Fla., Gaffalione expects to be soaring high if Sierra Leone wins.
“I’m living a dream right now. It’s hard to put into words. … I’ve definitely never had these feelings before. It’s pretty special,” he said in a recent Youtube interview at Churchill Downs.
“Growing up in the industry, this race has always meant the world to me. This is the one race we all want to win. Just to be able to ride in it is a privilege.”
The race will be simulcast at Tampa Bay Downs at 6:57 p.m., after the conclusion of the Oldsmar oval’s season-ending 10-race card. Advance wagering on the race will be available Friday and Saturday.
Gaffalione, who won last year’s Longines Kentucky Oaks on Pretty Mischievous and the 2019 Preakness on War of Will, competed on two occasions this year at Tampa Bay Downs. On the track’s March 9 Festival Day program, he won the Grade III Lambholm South Tampa Bay Derby for trainer Brown on Domestic Product, as well as the Grade III Michelob Ultra Challenger Stakes on Skippylongstocking.
Any thoughts Gaffalione might have had about riding Domestic Product in the Kentucky Derby ended after Sierra Leon’s performance in the Toyota Blue Grass. Instead, Domestic Product will be ridden by five-time Eclipse Award-winning Outstanding Jockey Irad Ortiz, Jr., who shares something in common with Gaffalione: neither has won a Kentucky Derby.
“To actually come here (Churchill Downs) and have a chance, I can’t think of anything better,” said Gaffalione, the son and grandson of jockeys. “Just to get a horse like this (Sierra Leone), it’s so exciting.”
The local excitement begins Friday with a nine-race Tampa Bay Downs card beginning at 12:15 p.m. Throughout the course of the afternoon, the track will honor its 2023-2024 human champions: Leading Trainer Kathleen O’Connell; Leading Jockey Samy Camacho; Leading Owner Juan Arriagada; and Leading Apprentice Jockey Gabriel Maldonado.
Following the ninth race, Tampa Bay Downs will simulcast the $1.5-million Longines Kentucky Oaks for 3-year-old fillies from Churchill Downs. Tampa Bay Downs fans have a major rooting interest in the track’s Suncoast Stakes winner, Power Squeeze, who will be ridden by six-time Oldsmar jockey champion Daniel Centeno.
Power Squeeze is on a four-race winning streak, scoring most recently under Centeno on March 30 in the Grade II Gulfstream Park Oaks Presented by FanDuel TV.
In the Kentucky Derby, four of the 20 horses, including Domestic Product, have competed at Tampa Bay Downs (there could be a fifth if there is a late scratch, allowing Mugatu to move from the also-eligible list into the race).
Already in the field with Domestic Product are West Saratoga, who finished third here in the Grade III Sam F. Davis Stakes and second in the Pasco Stakes; Grand Mo the First, who was third in the Lambholm South Tampa Bay Derby; and Catalytic, who finished second on March 8 in an allowance/optional claiming race.
West Saratoga will be ridden by two-time Tampa Bay Downs jockey champion Jesus Castanon.
Horses that won the Kentucky Derby after racing at Tampa Bay Downs are street Sense, who won the 2007 Tampa Bay Derby; Super Saver, the third-place finisher in the 2010 Tampa Bay Derby; and 2017 Kentucky Derby champion Always Dreaming, who broke his maiden here on Jan. 25 of that year.
Admission at Tampa Bay Downs on Saturday is $10, with children 17-and-under free. Valet parking is $25. The gates will open at 10 a.m., and the first local race will begin at 12:15 p.m. Automatic wagering terminals will be set up outside in front of the main Grandstand entrance for fans who decide to grab their tickets early and watch at home or elsewhere.
With post time for the Kentucky Derby seemingly getting later each year, the final minutes before the race are electric, as the realization sinks in that this is it for another year.
Plenty of Kentucky Derby souvenirs will be available in the Gift Shop, including glasses listing all 149 winners of the race. The cost is $14.95; if you want the traditional mint julep, the cost is $19 ($10 for the glass and $9 for the drink).
There will also be food-truck specials on the grounds, in addition to the usual concession and restaurant fare.
