5 times Kentucky Derby favorites broke our hearts

The fastest two minutes in sports has supplied some of the most surprising and heartbreaking finishes at Churchill Downs’ historic track.

With the 146th running of the Kentucky Derby inching closer, let’s look back at the five most disappointing finishes by favorites in the first leg of the Triple Crown.

Bellamy Road, 2005

Odds: 5-2

Bellamy Road didn’t carry the most outstanding résumé as a 2-year-old, but his 17 1/2-length conquest in the Wood Memorial (G1) thrust the 3-year-old into the spotlight ahead of the 2005 Derby.

Owned by Kinsman Stable — the racing stable of Yankees owner George Steinbrenner — Bellamy Road pulled in 5-2 odds as one of five entries for trainer Nick Zito.

Guided by jockey Javier Castellano, the colt got off to a solid start from post 16 and trailed leader High Fly at the quarter pole. Far behind them, 50-1 Giacomo had pushed into 11th, while 70-1 underdog Closing Argument, raced in fourth.  

In the final turn, Bellamy Road lost steam, and to everyone's shock, Giacomo closed to win. With Closing Argument in second, the $2 exacta paid $9,814.80.

Bellamy Road suffered a minor injury to his splint bone and came in seventh, but still ran faster than all four of Zito’s other entries. Later that fall, Bellamy Road placed second at the Travers S. (G1) and retired shortly after.

Unbridled’s Song, 1996

Odds: 5-2

Heading into the 122nd Kentucky Derby, all eyes focused on Unbridled’s Song, the winner of the Florida Derby (G1) and Wood Memorial earlier that spring. The son of Kentucky Derby and Breeders’ Cup Classic (G1) winner Unbridled entered the run for the roses as the 5-2 favorite, while another of Unbridled’s offspring, Grindstone, was at 6-1.

Owner Ernie Paragallo not only predicted Unbridled’s Song would earn the garland of roses, but also capture the Triple Crown and win out the remainder of his career. That prediction may have come true, had the gray colt not cracked his hoof in the Wood.

The injury required special bar shoes for the Derby, which jockey Mike Smith compared to “wearing combat boots and trying to run a foot race.” Despite that obstacle, Unbridled’s Song set the pace early in the 1 1/4 mile race and built a two-length lead around the final turn.

From there, the 3-year-old tired and finished fifth. As for Grindstone, the D. Wayne Lukas entry bested Bob Baffert trainee Cavonnier in one of the closest finishes in Derby history.

Arazi, 1992

Odds: 4-5

Few horses generated the kind of hype Arazi did ahead of the 1992 Derby.

The chestnut colt from France claimed the Breeders’ Cup Juvenile (G1) at Churchill Downs in 1991, after he won six straight races against top European competition.

Considered one of the most impressive performances in Breeders’ Cup history, his five-length feat had the media and fans praising his potential.   

Time magazine labeled Arazi “the second coming of Secretariat,” while the New York Times described him as “mythical.”

No one expected Arazi to lose the Derby, especially after his top competition, A.P. Indy, scratched the morning of the race. Nonetheless, knee surgery prior to his Derby run and his outside post position presented steep hurdles.

Arazi finished eighth, 8 1/2 lengths behind 16-1 longshot winner Lil E Tee.

Holy Bull, 1994

Odds: 2-1

Unbeaten as a 2-year-old, Holy Bull continued his dominance early in his 3-year-old campaign, as he claimed the Florida Derby and Blue Grass (G2) in the lead-up to the Kentucky Derby.

The colt had lost just once, in the Fountain of Youth (G2), but a sloppy track on the first Saturday in May derailed his hopes of another commanding performance.

The gray owned and trained by Warren Croll Jr. finished 12th out of 14 horses. Croll later alleged Holy Bull had been drugged before the race and doubled down on that claim after the speedster reeled off six straight victories, including wins in the Metropolitan H. (G1), Dwyer (G2), Haskell (G1), and Woodward (G1).

Holy Bull earned American Horse of the Year in 1994, then retired to stud in 1995. Giacomo is his son, along with U.S. champion 2-year-old male Macho Uno and Stephen Foster Handicap winner Flashy Bull.

Point Given, 2001

Odds: 9-5

Nicknamed “The Big Red Train” and “T-Rex,” Point Given possessed the pedigree and physique to become a Triple Crown champion.

The Baffert-trained chestnut won eight graded stakes, including the Travers, Haskell, and Breeders’ Cup Juvenile.

Only once did he finish out of the money, and that result occurred on May 5, 2001.

Off as the 9-5 favorite, Point Given seemed like a shoo-in for success. But the colt appeared a bit uneasy and reared repeatedly during a routine gallop the morning of the Derby.

Later that day, he hardly pressed for the lead. Some blamed jockey Gary Stevens for making a move too early on the backstretch. Stevens believed a foot infection in one of Point Given’s back feet contributed to his unsatisfactory fifth-place finish.   

Monarchos (10-1) crossed the finish line first in 1:59:97, the second-best time by a Derby winner, behind Secretariat.

In the Preakness (G1), the gray colt came back to earth, as Point Given won the second leg of the Triple Crown by 2 1/2. If that win didn’t erase the pain of Point Given’s Derby performance, the Belmont Stakes (G1) surely helped.

In one of the fastest times in the history of the race, Point Given crushed his competition with a 12 1/4-length victory. He later collected Horse of the Year and was named champion 3-year-old male by unanimous selection.