Kentucky Derby Lucky Loser – Forty Niner (1988)

Oct 16, 2026 Jennifer Kelly

Forty Niner (Photo by Coglianese Photo)

Think about your favorite racehorses and what you love about them. Is it Queen Z’s late sweep to the wire? Man o’ War’s blazing speed? Affirmed’s tenacity? Seabiscuit’s rags-to-riches story? In the case of Forty Niner, as his trainer Woodford C. ‘Woody’ Stephens put it, “he was just a dead game horse—just game as they come.”

Though Forty Niner just missed wearing roses in 1988, he went on to a celebrated career on and off the track, a champion representing a storied tradition of Thoroughbred greatness.

Golden Roots

The 1970 crop included 24,361 foals, and once all was said and done, it might be one of the best crops ever, given the names that emerged: Dahlia, Stop the Music, Café Prince, Desert Vixen, La Prevoyante, Sham, Forego, and Secretariat. Oh, and one more: Mr. Prospector.

A fair racehorse, the son of Raise a Native was speedy but prone to injury. Though he won seven of his 14 starts, no one could have anticipated what he would become as a sire. By 1985, he had produced Preakness winner Tank’s Prospect and Belmont Stakes victor Conquistador Cielo. He was Claiborne Farm’s leading stallion, a natural choice for the mare File, a daughter of Preakness winner Tom Rolfe. On May 11, 1985, File foaled a chestnut colt with a white diamond on his forehead and a hind sock.

With Mr. Prospector as sire and Gold Digger as granddam, File’s newest colt was named Forty Niner and went to the barn of Hall of Fame trainer Woody Stephens when it was time to hit the racetrack. Stephens had been behind Swale’s Kentucky Derby and Belmont Stakes wins for the famed breeder and owner. From the first, the colt showed how good he was, winning his debut, a six-furlong maiden special weight at Belmont Park, by 3 ¼ lengths.

In his next start, Forty Niner stepped up to stakes company in the Saratoga Special (G2), where he got out to a fast start and then faded to sixth. But nearly two weeks later, he reversed form and blew everyone away in the Sanford (G2), where his 3 ½-length victory put the colt’s name on the list for the 1988 Kentucky Derby. Subsequent wins in the Futurity Stakes (G1), the Champagne (G1), and the Breeders’ Futurity at Keeneland, electing to bypass the Breeders’ Cup Juvenile at Hollywood Park.

With five wins in six starts, Forty Niner earned the Eclipse Award for Champion Two-Year-Old Colt and entered the new year with roses in his eyes.

Full Steam Ahead

Stephens sent Forty Niner south to open his three-year-old season, opting for the Hutcheson Stakes at Gulfstream Park, where he was upset by Perfect Spy in the seven-furlong test. “If you’re going to lose, this is the time to get beat,” Stephens said after the race. With three months to go before the Run for the Roses, the colt had plenty of time to develop before going after the big prize.

Two weeks later, Forty Niner was back in the gate for the Fountain of Youth (G2), an 8 ½-furlong test for the son of Mr. Prospector. With regular rider Eddie Maple in the saddle, he would duel D. Wayne Lukas’s Notebook down the Gulfstream stretch to win by a nose. His trainer was pleased with the win, telling reporters, “I couldn’t be more pleased with his race. I couldn’t believe, off that one race, he ran as tough as he did. He didn’t look distressed in the winner’s circle, but he had to be a little tired after that.”

In his next race, the Florida Derby (G1), Forty Niner led from the gate but was passed in the final strides by longshot Brian’s Time. That close second did not ding his chances of going into the first Saturday in May as the favorite, but Stephens gave his star a four-week break before sending him to Keeneland for final preparations. There, he got a rider change from Eddie Maple to Pat Day, who was still searching for his first Kentucky Derby win. In their first trip together, they won the seven-furlong Lafayette, finishing five lengths ahead of Buoy. But his final Derby prep in the Lexington (G2) eight days later saw Forty Niner run into another rising star: Risen Star, the son of Secretariat, who came north from Louisiana to establish himself as another contender for the Run for the Roses. Risen Star led at the wire, denying Claiborne Farm in the same race Swale lost in 1984, right before he went on to win the Kentucky Derby.

That led to the first Saturday in May and another meeting between many of the year’s best three-year-olds. The field included Seeking the Gold, another son of Mr. Prospector also foaled at Claiborne; Brian’s Time, who defeated Forty Niner in the Florida Derby; recent rival Risen Star; and Winning Colors, the filly who defeated the boys in the Santa Anita Derby (G1). At the break, jockey Gary Stevens gunned the filly to the lead, building a four-length advantage by the three-quarters mark, and held off the late-charging Forty Niner to win by a neck.

In the Preakness, Stephens saw the writing on the wall and sent Forty Niner to the lead rather than let Winning Colors run unchallenged and duplicate her Derby trip. However, that strategy burned the son of Mr. Prospector out in the stretch, and he faded to seventh. However, the filly also couldn't hold on to second and finished third behind Risen Star and Brian’s Time.

Stephens gave Forty Niner a breather after seven races over the first half of 1988. With late-summer stakes ahead, the colt needed the freshening.

Legacy of Longevity

With their sights set on the Haskell, Stephens brought Forty Niner back in a one-mile allowance at Monmouth Park. With Julie Krone in the saddle, the colt sat second until the stretch, where he moved to an easy lead and bested the track record for a mile by 4/5 of a second. The Haskell was another battle, this time with Seeking the Gold, the pair dueling down the Monmouth stretch, with Forty Niner coming out on top by a nose.

Next came a trip to Saratoga and the Travers, the Midsummer Derby. Again, Seeking the Gold and Brian’s Time were among the challengers, as was Dynaformer, the Jersey Derby winner. But the 10 furlongs came down to another battle between Forty Niner and Seeking the Gold, who hooked up in the stretch and again finished head-to-head to the wire, with the Claiborne Farm color-bearer coming out on top by a nose. His Travers victory gave Woody Stephens his first win in that Grade 1 classic.

Ahead of the Breeders’ Cup Classic at Churchill Downs later that fall, Forty Niner faced older horses for the first time in the 10-furlong Woodward. Waquoit led throughout the first six furlongs, but both the three-year-old and 1987 Kentucky Derby winner Alysheba moved to challenge him on the far turn. Forty Niner led at the top of the stretch, but Alysheba, carrying seven more pounds, ran him down in the final strides to win by a neck.

A victory in the inaugural NYRA Mile at Aqueduct gave Forty Niner some winning momentum going into the Breeders’ Cup. The field he would face, though, was stacked: Seeking the Gold, Cryptoclearance, Alysheba, and more. With Julie Krone in the saddle, the son of Mr. Prospector did not have enough in the tank to challenge Alysheba as night descended on Churchill Downs. He passed tired horses late to finish fourth in his final start; retirement at his birthplace was Forty Niner's next move.

He spent six years at Claiborne, siring Belmont Stakes winner Editor’s Note; Distorted Humor, who later became the sire of classic winners like Funny Cide himself; and stakes winner Roar, Hall of Famer Rachel Alexandra’s damsire. The Japan Bloodhorse Breeders' Association bought the son of Mr. Prospector for a reported US$10 million in 1995, keeping him at Shizunai Stallion Station until he was pensioned in 2007. This fan favorite lived to be 35 and died of old age in Japan on May 17, 2020.

Though he just missed by a neck under the Twin Spires, Forty Niner showed his gameness again and again, prevailing over his peers in races like the Travers Stakes by the barest of margins. Called “my most favorite horse” by Seth Hancock, this chestnut son of Mr. Prospector lives on in the memories of those performances against some of his era’s best, from Kentucky Derby winners to Hall of Famers, a lucky loser who made his mark on the sport we love.