In June 2018, Justify celebrated a win in the Belmont S. (G1). By September, unraced since the Belmont, he had retired to stud as the only Triple Crown winner to end his career undefeated.

The only other horse to secure the Triple Crown while unbeaten was Seattle Slew, but he went on to race eight more times after the Belmont and finished with a 17-14-2-0 record in 1978.

While many Kentucky Derby winners have raced long after their trip to the winner’s circle at Churchill Downs, quite a few disappeared from the racetrack, or struggled to win another event, following victory in one of the most prestigious races in the world.

Below we explore five of the best horses of the last 40 years to triumph in the Kentucky Derby and then fade from the limelight, whether through early retirement or an inability to replicate their success on the first Saturday in May.

1. Nyquist, 2016

Champion Two-Year-Old Nyquist owned a 7-7-0-0 record heading into the 2016 Kentucky Derby, with victories on debut at Santa Anita as well as in the Best Pal (G2), Del Mar Futurity (G1), FrontRunner (G1), Breeders’ Cup Juvenile (G1), San Vincente (G2), and Florida Derby (G1).

On May 7, 2016, he went off as the 2.30-1 favorite among a field of 20 and crossed the wire first by 1 1/4 lengths to become just the second horse to win both the Juvenile and Derby, as well as the eighth undefeated winner of the Kentucky Derby.

But Nyquist’s visits to the winner’s circle came to a halt from there. In the Preakness S. (G1), he finished more than three lengths in third to Derby second-place finisher Exaggerator, then withdrew from the Belmont due to a high leucocyte count.

He again lost to Exaggerator when 3 1/2 lengths in fourth in the Haskell (G1), before he came home sixth in the Pennsylvania Derby (G2) at Parx in September 2016.

Nyquist’s connections planned to run him in the Breeders’ Cup Classic (G1) to close out the season, but the horse was withdrawn after a sluggish workout on the Thursday before the race. He retired to stud shortly after, and by March 2023 had sired champion juveniles Vequist and Gretzky The Great among 16 stakes winners from his first three crops.

2. I'll Have Another, 2012

The son of Flower Alley showed flashes of promise during his two-year-old season, winning on debut in a maiden special weight at Hollywood Park and placing second in the Best Pal before struggling over a sloppy track in the Hopeful S. (G1) in September.

But in 2012, I’ll Have Another took a huge step forward, with victories in the Robert B. Lewis S. (G2) and Santa Anita Derby (G1). As a 15-1 choice in the 2012 Kentucky Derby, the Doug O’Neill pupil surprised 4.30-1 favorite Bodemeister when beating him by 1 1/2 lengths to claim the first leg of the Triple Crown.

Bodemeister was again sent off as the post-time favorite in the Preakness, but I’ll Have Another had his number once again.

With a chance to become the first Triple Crown winner since Secretariat, the chestnut colt drew post 11 in the 12-horse Belmont field. However, a tendon injury prevented him from running the Belmont and he was subsequently retired from racing. He was the third horse, behind Burgoo King (1932) and Bold Venture (1936), to scratch from the Belmont after winning the Kentucky Derby and Preakness.

He ended up at stud in Japan, where he sired four stakes winners from six crops, and since 2019 has been at Ocean Breeze Ranch in California.

3. Smarty Jones, 2004

A fractured skull nearly kept Smarty Jones from a career in racing when he hit his head in the starting gate during a training session in 2003. Yet, the son of Elusive Quality overcame a major setback and not only made his debut at Philadelphia Park in November 2003, but went on to win eight straight races, including the 2004 Kentucky Derby and Preakness.

On June 5, 2004, the John Servis trainee went off as the heavy favorite in the Belmont and was ultimately passed by 36-1 Birdstone in the stretch to finish second — the lone loss of Smarty Jones’ nine-race career.

The chestnut had never been passed before that day and would never race again. Voted Champion Three-Year-Old in 2004, he was retired to stud after bruising in his cannon bones was discovered ahead of a planned start in the Pennsylvania Derby (G2). At stud he’s sired 31 stakes winners, including Grade 1 victor Centralinteligence, and was champion sire in Uruguay in 2016-17.

4. Grindstone, 1996

Grindstone was a 5.90-1 winner of the Kentucky Derby and the less heralded Unbridled colt among the field of 19. Also by Unbridled, Unbridled’s Song earned 3.50-1 favoritism ahead of the race, but the D. Wayne Lukas-trained Grindstone ultimately possessed the stamina to get up by a nose and triumph in the 1996 Derby.

Prior to the first leg of the Triple Crown, Grindstone won the-then Grade 3 Louisiana Derby and placed second in the Arkansas Derby (then a Grade 2) and an allowance at Santa Anita.

As a two-year-old, he broke his maiden at Belmont Park in June 1995, before failing as the favorite in the six-furlong Bashford Manor S. at Churchill Downs.

Following the Derby, Grindstone was retired five days later, when a bone chip was found in his knee. He became the first horse since Bubbling Over (1926) to retire immediately following a Derby win. In 2019, Country House would also experience a similar fate, concluding his career with a 7-2-2-1 record.

Grindstone was also the first Kentucky Derby winner to stand in the Northwest. He sired Belmont and Travers (G1) hero Birdstone, who sired 2009 Kentucky Derby winner Mine That Bird and 2009 Belmont winner Summer Bird.

5. Spend a Buck, 1985

Never finishing out of the money in 15 career races, Spend a Buck already boasted a 7-2-2 record from 11 starts before prevailing in the Run for the Roses on May 4, 1985.

But what made the Buckaroo colt especially unique was the fact he skipped the Preakness and Belmont to instead race in the Jersey Derby, as Garden State Park owner Robert Brennan offered a $2 million bonus to the horse that came out victorious in that year’s Kentucky Derby, the May 27 Jersey Derby, and two April prep races — the Cherry Hill Mile and the Garden State S., both of which Spend a Buck had won prior to the first Saturday in May.

Following victory in the Jersey Derby, Spend a Buck would race only two more times, finishing second in the Haskell and first in the Monmouth Handicap (G1) — now the Philip H. Iselin S. (G3) — where he set a track record of 146.80 seconds for 1 1/8 miles that stood until 2022. An injury to his right ankle forced his retirement of September 1985, but Spend a Buck went on to a successful career at stud, particularly in Brazil. A number of his leading Brazilian-bred runners, including Einstein, Hard Buck, and Pico Central, became notable performers in North America.

Spend a Buck’s shocking absence in the Preakness and Belmont also prompted Pimlico and Belmont Park to offer a $5 million bonus to any colt who swept the Triple Crown series in order to encourage participation in the future. The bonus was discontinued in 2005, 10 years before American Pharoah finally broke a 37-year Triple Crown drought.