The 5 greatest trainers that have never won the Kentucky Derby

April 22nd, 2021

Whether it’s fair or not, a horseman’s greatness is often determined by their level of success in the Triple Crown races, particularly the Kentucky Derby (G1). It’s the race that everyone in the sport wants to win, so even some of the most accomplished trainers in horse racing history have had their fair share of difficulty in reaching the winner’s circle.

Here are the five best trainers who have never won the “Run for the Roses.”

5. Chad Brown

Wins: 1,944 (outside Top 50)

Earnings: $199.6 million (eighth)  

A winner of four straight Eclipse Awards for Outstanding Trainer from 2016 to 2019, Chad Brown still has plenty of chances to win the Kentucky Derby, as he’s only 42 years old.

Brown is generally considered a world-class turf trainer, but he’s had plenty of success with dirt runners, three-year-olds included. He’s had five starters in the “Run for the Roses,” with Good Magic’s runner-up finish in 2018 being the closest he’s gotten to a victory.

Brown has at least a puncher’s chance in the 2021 Derby with Highly Motivated, the Blue Grass S. (G2) runner-up.

4. Bobby Frankel

Wins: 3,654 (20th)

Earnings: $227.9 million (sixth)

A five-time Eclipse Award-winning conditioner, the late, great Bobby Frankel came painstakingly close to Derby glory in his esteemed career, but never quite got over the hump.

His first close call came in 2000 with Aptitude, who beat all comers except favored Fusaichi Pegasus.

In 2003, Frankel boasted public choice Empire Maker, but he was upset by Funny Cide. Empire Maker would avenge that defeat in the Belmont S. (G1), but it didn’t fill the hole in an otherwise impeccable Hall of Fame résumé for Frankel.

3. H. Allen Jerkens

Wins: 3,859 (17th)

Earnings: $103.8 million (25th)

The venerable H. Allen Jerkens is often remembered as a destroyer of legends, not a builder of them. “The Giant Killer” twice beat the mighty Secretariat, with Onion in the Whitney (G1) and Prove Out in the Woodward (G1).

But Jerkens wasn’t just some dog who had his day in 1973, the year he won his lone Eclipse Award. He was inducted into the Hall of Fame in 1975 at just 46 years of age, and trained many noteworthy Grade I winners over his career, like 1993 Triple Tiara victress Sky Beauty.

However, Jerkens trainees made just three appearances all-time in the Kentucky Derby, and none hit the board. Longshot Round Stake was 11th in 1975, Sensitive Prince finished sixth in 1978, and Devil His Due checked in 12th in 1992.

2. Jerry Hollendorfer

Wins: 7,679 (third)

Earnings: $202.9 million (seventh)

West coast mainstay Jerry Hollendorfer has been blessed with many talented runners over his illustrious career. Breeders’ Cup Juvenile Fillies victress Songbird was his biggest earner on-track ($4.69 million), with Kentucky Oaks (G1) winner Blind Luck a close second ($3.27 million).

His most talented male runner was arguably Shared Belief, but an injury unfortunately delayed the 2013 CashCall Futurity (G1) winner’s three-year-old debut until after the “Run for the Roses.”

The closest Hollendorfer has come to capturing the Derby was in 2017, when Battle of Midway ran third.

1. Steve Asmussen

Wins: 9,288 (second)

Earnings: $352.9 million (second)

A two-time Eclipse Award-winning trainer, Steve Asmussen is within range of passing Dale Baird for most all-time wins this year. His powerhouse stable has been represented in over 45,000 races, by far the most in history. Asmussen has won the Preakness (G1) twice and the Belmont once, but the Derby has proven elusive.

The Texas native has entered 21 horses in the Kentucky Derby, but has not yet managed to win the nation’s most prestigious race. He ran second on two occasions, with Nehro in 2011 and Lookin At Lee in 2017.

If all goes according to plan, he’ll saddle Arkansas Derby (G1) winner Super Stock and Lecomte S. (G3) winner Midnight Bourbon in the 2021 Kentucky Derby.

All stats are derived from and are accurate as of April 21, 2021.