Kentucky Derby’s Lucky Losers: Skywalker (1985)

Feb 28, 2025 Jennifer Kelly

The Star Wars saga shares the heroic journey of Luke Skywalker, Han Solo, Princess Leia, and an ever-expanding cast of characters, a vast universe of stories set in a galaxy far, far away. The imminent return of another popular Star Wars series, Andor, once again brings us back into the world of the Empire and the Rebellion, where hope fuels another generation to fight back against the darkness.

Skywalker's journey to racing glory included a notable, if not victorious, appearance in the Kentucky Derby (G1). While he didn't capture the roses, his presence in the prestigious race added a chapter to his storied career. More than just a Derby participant, Skywalker went on to achieve significant wins, most famously in the Breeders' Cup Classic (G1). Much like his namesake Star Wars hero, this hard-trying racehorse overcame injury to triumph in one of the sport’s great stakes races.

A New Hope

Stone Farm has been the birthplace of Kentucky Derby winners like Gato Del Sol, Sunday Silence, and Fusaichi Pegasus, and classic winners like Risen Star. Owner Arthur Hancock III is the son of Arthur “Bull” Hancock Jr., who ran Claiborne Farm from 1957 until his death in 1972 and parlayed what he learned from his father into his breeding program at Stone Farm. His connection with Tom Tatham, the leading partner in Oak Cliff Thoroughbreds, not only yielded Sunday Silence, Hall of Famer and Japanese supersire, but also another Kentucky Derby hopeful and stakes winner in Skywalker.

Tatham spotted the stakes-winning mare Bold Captive at a California breeding stock sale in January 1982. In foal to Relaunch, Del Mar Derby (G3) victor, he got the mare for $350,000 and brought her back to Kentucky, where she foaled a dark bay colt with a smudge of white on his forehead on March 4. Tatham’s son Casey christened Bold Captive’s new foal Skywalker after the hero of the popular Star Wars movie franchise and prepared him to run in the Oak Cliff colors, sending him to the barn of Michael Whittingham, Hall of Fame trainer Charlie’s son, at Santa Anita.

Skywalker debuted in late November 1984 in a one-mile maiden race at Hollywood Park. With future Hall of Famer Eddie Delahoussaye in the saddle, the son of Relaunch was last after the first quarter but progressed nicely through the field to hook up with Fast Account late and then eke out the win by a nose. A step up to stakes company in his next start, the Hollywood Futurity (G1), was not as successful, Skywalker finishing fifth in the field of 13.

Even though the colt’s first try in stakes company was not a success, Whittingham had enough faith in Skywalker to circle the first Saturday in May on his calendar, his hopes high for his first potential Derby starter.

SKYWALKER (USA) 1982
(RELAUNCH -- BOLD CAPTIVE BY BOLDNESIAN)
B/ O Oak Cliff Stable (Ky) Mar 4, 1982
T/ Michael C Whittingham
20-8-3-3—--2,226,750 dls
Breeder's Cup Classic G1, Longacres Mile G2, Mervyn LeRoy H G2, San Diego H G3, Santa Anita Derby G1 pic.twitter.com/2PjrMlFkzV

— HORSE RACING 100 (@HORSERACING1002) April 22, 2023

The Force Awakens

Skywalker started his three-year-old season with a win in an allowance at Santa Anita with Pat Day on his back. “This colt impresses me,” the jockey said after the race. “He’s maturing quickly, and I even liked him in that race at Hollywood Park [the Hollywood Futurity]. He finished fifth but broke in a tangle, got in trouble a couple of times, and still finished with a lot of run.” With that positive report, Whittingham sent his colt to Bay Meadows for the 1 1/16-mile El Camino Real Derby (G3). Traffic issues in that race once again cost Skywalker the win; anytime Day tried to find a hole to squeeze through, it would close on him, which caused the colt to interfere with other horses enough to be disqualified from third to fourth.

Back at Santa Anita, Skywalker just missed in the San Felipe (G1) in mid-March, finishing a nose back of Image of Greatness. Then came the Santa Anita Derby (G1), where Skywalker had the lead with a quarter of a mile left to go in the nine-furlong test, but new jockey Laffit Pincay, Jr. realized that his mount was loafing and that Fast Account was looming. When the latter took over, Pincay went to the whip, which Whittingham had advised he use sparingly, and tapped Skywalker, who pulled even with Fast Account and then eked out a nose advantage at the wire. With four weeks to go, Skywalker had emerged from the Derby prep season as California’s leading candidate for the big race.

At Churchill Downs on May 4, 1985, Skywalker entered the starting gate with 12 others, including Chief’s Crown, winner of the inaugural Breeders’ Cup Juvenile (G1); Tank’s Prospect, winner of both the El Camino Real and Arkansas Derbies (G1); and Spend a Buck, third in the Breeders’ Cup Juvenile and winner of the Arlington-Washington Futurity (G1). Though Pincay was on board for his Santa Anita Derby win, the jockey took the mount on Stephan’s Odyssey for the Derby, and Eddie Delahoussaye was back in Skywalker’s saddle for the big race. Breaking from post 12, the son of Relaunch raced wide throughout, hanging out mid-pack and never progressing beyond sixth.

Skywalker came out of the race with a stress fracture in one knee, sidelining him until late in the year. Then, as he was preparing to come back, the colt popped a splint, so Whittingham decided to stop on him. This Jedi namesake would come back at age four to find the winner’s circle again.

The Last Jedi

He started with a third in an allowance at Santa Anita, 11 months after his last start in the Kentucky Derby. Then, Skywalker notched wins in the Mervyn LeRoy H. (G2), the San Diego H. (G3), and then in the Longacres Mile (G2) before arriving at the third Breeders’ Cup on familiar ground at Santa Anita. The field included Precisionist, who had won the previous year’s Breeders’ Cup Sprint (G1) as well as the 1986 Woodward (G1); Turkoman, the son of Alydar who had outdueled Precisionist in the Marlboro Cup (G!); and European star Tryptich, who had finished second in the 1985 Epsom Oaks (G1) and won the Irish 2000 Guineas (G1) at three and then the Champion (G1) at Ascot at age four.

The race was down to Precisionist versus Turkoman, but Michael Whittingham had been pointing Skywalker to the Classic since that first start in April. The goal was “not to take a lot out of him, just a step at a time, with the idea to peak here,” the trainer shared. He entered the gate at odds of 10-1, Pincay once again in the saddle. They broke cleanly, running third behind Precisionist and Herat, who set a brisk pace. By the top of the stretch, both of those horses were done, which allowed Skywalker to take over as Turkoman made his bid in the straight. The latter overtook Precisionist but could not catch Skywalker, who took the Classic by 1 1/4 lengths. While others might have been surprised at the effort, Pincay was not: “He wasn’t a surprise for me. I’ve always been high on this horse,” the famed jockey shared after the race.

At age five, Skywalker suffered an injury while training for the Santa Anita H. (G1) and was sent to Cardiff Stud near Creston, California, to cover mares while he recovered. He then unretired to pursue a second Breeders’ Cup Classic in 1987. He ran four times that season, winning once, placing in two stakes, and then finishing 12th and last in the Classic, his lack of seasoning and aggravated injury catching up to him. He stood stud at Cardiff until 1996, when he returned to his birthplace, Stone Farm, where he lived until his death in 2003.