Double the Joy: Trainer/Jockey Duos Who Won Roses and Lilies

The 150th Kentucky Oaks (G1) and Kentucky Derby (G1) were memorable for more than the milestone anniversaries for both classics. When Thorpedo Anna took the Oaks and then Mystik Dan eked out a Derby victory, they gave Kenny McPeek and Brian Hernandez Jr. a rare double victory, just the third trainer/jockey combo to win both races in the same year. The previous pairs include multiple Hall of Famers, each leaving their mark on the sport through their achievements under the Twin Spires. 

Don Meade, Herbert Thompson, and Colonel E.R. Bradley (1933)

Herbert J. Thompson was nicknamed “Derby Dick” for a good reason: by 1933, the trainer had won three for owner Colonel E.R. Bradley’s Idle Hour Farm. Bradley had plunged into racing and breeding in the early years of the 20th century while Thompson had taken over the Idle Hour stable in 1918. Together, the pair had top two finishers in both 1921 and 1926 and then turned the Derby-Preakness double in 1932 with Burgoo King. Don Meade was only 20 years old and four years into his riding career when Thompson tapped him to ride in the 1933 Derby on Brokers Tip and the Oaks on Barn Swallow. 

Brokers Tip came to Louisville winless in his five lifetime starts, but with three in-the-money finishes already on his resume. The race was wide open with the entry of Ladysman and Pomponius as tepid favorites while Brokers Tip went off at 9-1. Turning into the stretch, Meade and Brokers Tip had only Charley O and Head Play ahead of them. The rider sent his colt to the rail and came up on Head Play’s inside. Herb Fisher on Head Play tried to box Brokers Tip in so Meade reached over to grab his rival’s saddlecloth. The two jockeys duked it out, exchanging pushes and blows all the way to the wire, their mounts head-to-head at the finish. With no photo finish camera, the decision came down to the stewards who ruled in favor of Brokers Tip. 

Two weeks later, Meade was aboard Barn Swallow in the nine-furlong Oaks. The filly had been a stakes winner at two and came to Louisville as the favorite in a short field of five. Meade sent her straight to the lead and made every pole a winning one, taking the 59th Kentucky Oaks by three lengths. Her victory was the first and only Oaks for the trio and the first Oaks/Derby double for the same jockey, trainer, and owner. 

Eddie Arcaro, Ben Jones, and Calumet Farm (1952)

Given Calumet Farm’s dominance in the 1940s and 1950s, their presence on this list is unsurprising. The devil red and blue silks produced eight Kentucky Derby and six Kentucky Oaks winners, most coming in those two decades. As the first weekend in May 1952 approached, the era’s leading owner had the favorites for both classics. Guiding those favorites were trainer Ben Jones and jockey Eddie Arcaro, the duo who had already teamed up to win two Triple Crowns in the 1940s and continued that relationship into the following decade. 

Real Delight approached her turn in the Oaks with just four lifetime starts under her belt. A splint had kept her off the racetrack until her three-year-old season, but the duo of Jones and his son Jimmy had the filly more than prepared for the nine-furlong feature. With Arcaro in the saddle, Real Delight broke cleanly, sat fifth early, and then wound her way through the front four to take the lead in the stretch and win by 1 3/4 lengths. 

The next day, Arcaro was back in the saddle for Jones and Calumet, this time on Hill Gail in the Kentucky Derby. After winning the San Vicente and the Santa Anita Derby, the Bull Lea colt came east to win the Derby Trial four days before the big race. Breaking from the inside post, Hill Gail swerved toward the outside, trailed Hannibal until the six-furlong mark, and then powered home two lengths in front at the wire. 

An injury sustained in the Derby prevented Hill Gail from pursuing a Triple Crown and from finding that consistent form again. Real Delight went undefeated for the remainder of her three-year-old season, taking the Black-Eyed Susan and the Coaching Club American Oaks among her nine stakes wins that season. 

RELATED: 10 Top Winning Kentucky Derby Jockeys of All Time

Brian Hernandez and Kenny McPeek (2024)

This year’s winning trainer and jockey duo of McPeek and Hernandez both achieved their respective career milestones of winning these two classic races.

McPeek took out his trainer’s license in 1985 and has built his career with modestly priced horses that become graded stakes winners. He won the 2002 Belmont S. (G1) with longshot Sarava and then a pandemic-delayed Preakness S. (G1) with Swiss Skydiver in 2020. Mystik Dan’s Derby victory gives the Arkansas native a win in all three Triple Crown races. 

Hernandez started his professional riding career in 2003 and won the 2004 Eclipse Award for apprentice jockey. His Oaks win on Thorpedo Anna is his first in that fillies’ classic after five previous tries. He has ridden in all three Triple Crown stakes, including four previous Derby mounts, before winning with Mystik Dan. He has been in the saddle for all of Thorpedo Anna’s five starts, including her two stakes wins, and has piloted Mystik Dan in all but one of his seven starts, including the Goldencents colt’s victory in the Southwest S. (G3).