The best jockeys that have never won the Kentucky Derby

April 29th, 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 jockeys in horse racing history have had their fair share of difficulty in reaching the winner’s circle.

Last week we counted down the five best trainers who have never won the “Run for the Roses.” Now we’ll highlight the five best jockeys in history who are without a Kentucky Derby triumph on their résumé.

5. Corey Nakatani

Wins: 3,909 (86th)
Earnings: $234.6 million (13th)

Corey Nakatani was wildly successful in the Breeders’ Cup, winning 10 races between 1996 and 2012. But that success did not transfer to the Triple Crown trail.

Nakatani placed in only one of the three classic races for three-year-olds, when he was second aboard Nehro in the 2011 Kentucky Derby. He was 0-for-17 lifetime in the “Run for the Roses.”

The California native was passed over for Hall of Fame induction in 2020 but could be voted in this year.

4. Javier Castellano

Wins: 5,355 (25th)
Earnings: $356.9 million (second)

At age 43, time could be running out for Javier Castellano to get that elusive Kentucky Derby victory.

The four-time Eclipse Award-winning rider – voted into the Hall of Fame in 2017 – is 0-for-14 lifetime in the “Run for the Roses.” Castellano’s best finish in Churchill Downs’ signature event came in 2018, when he was third atop Audible.

The two-time Preakness winner will be aboard the Chad Brown-trained Highly Motivated – last seen running second in the Blue Grass Stakes (G2) – in the 2021 Kentucky Derby

3. Irad Ortiz, Jr.

Wins: 2,776 (outside Top 100)
Earnings: $207 million (16th)

Irad Ortiz Jr. has already put together a résumé worthy of the Hall of Fame, and he’s only 28 years old.

The Puerto Rico native is an 11-time Breeders’ Cup winner, and has a Belmont Stakes score (2016, Creator) to boot. Ortiz Jr. has also taken each of the last three Eclipse Awards for Outstanding Rider.

However, he’s not had much luck in the Kentucky Derby thus far. Ortiz Jr. is 0-for-4, with his best finish being a fourth-place result with favored Improbable in 2019.

He’ll be aboard one of the top betting choices in Florida Derby (G1) victor Known Agenda in this year’s “Run for the Roses,” but the Todd Pletcher trainee drew the dreaded one post, which no horse has won from since 1986 (Ferdinand).

2. Garrett Gomez

Wins: 3,769 (98th)
Earnings: $205.2 million (17th)

The late, great Garrett Gomez was a 13-time Breeders’ Cup winner and a two-time Eclipse Award recipient, but he was never able to experience a Kentucky Derby victory.

Gomez came as close as second place in 2009, when Pioneerof the Nile was upset by Mine That Bird in a muddy renewal of the Derby.

Despite his shortcomings in the Triple Crown series, Gomez was inducted into the Hall of Fame in 2017.

1. Ramon Dominguez

Wins: 4,985 (37th)
Earnings: $191.6 million (21st)

Ramon Dominguez’s standing on the all-time leaderboards would be even higher had he not been forced to retire due to a traumatic brain injury suffered in a spill in 2013.

Fans of Dominguez can point to his three Eclipse Awards earned from 2010 to 2012, and his Hall of Fame status, which he earned in 2016. He was also a three-time Breeders’ Cup victor, and placed in the Top 5 in wins nationwide in every year from 2003 to 2012.

But one thing missing from Dominguez’s list of accomplishments is a Triple Crown race triumph. He placed in the Kentucky Derby only once, when second atop Bluegrass Cat in 2006.  

All stats are derived from and are accurate as of April 28, 2021.