The 2026 Kentucky Derby is less than four weeks away. The annual event is not only the most anticipated, most watched Thoroughbred race in the world but an essential part of American sports culture.
Memories are made with each Run for the Roses, but some over the passage of time become legend, not only to day-to-day followers of horse racing but to the general public.
The first Saturday in May memories usually involve a heavily favored horse Winning and thus etching his or her name into the history books, but there have been some upsets for the ages as well.
This year’s Kentucky Derby is May 2nd. Over the next few weeks, the Daily Racing Blog will look back at some of the biggest Derby upsets at Churchill Downs.
That said, first up we give you:
GIACOMO (2005) The epitome of the old axiom: pace makes the race. Derby 131 featured two solid favorites in Wood Memorial Winner BELLAMY ROAD (ML 5-2) and Arkansas Derby Winner AFLEET ALEX (ML 9-2) but otherwise a wide-open race in terms of handicapping.
The race unfolded like something from the Ruidoso Downs Quarter Horse circuit early on, as SPANISH CHESTNUT led the field through opening quarter-mile splits of :22.28 and 45.38.
By the time the field turned for home, there were about 10 horses seemingly with a chance, but most of them were already dropping anchor.
CLOSING ARGUMENT, a 71-1 shot, dueled with AFLEET ALEX in the final sixteenth of a mile, but then both were passed on the outside by a grinding 50-1 shot named GIACOMO.
GIACOMO entered the Kentucky Derby with one Win from seven starts for his connections and had previously finished 4th in the Santa Anita Derby.
But on this day in May with Mike Smith in the irons, the big gray colt trained by John Shirreffs Won by a half-length over CLOSING ARGUMENT, while AFLEET ALEX hung on for 3rd place.
The payouts were, as you would expect with a $102 dollar Winner on top, astronomical.
The $1 Superfecta paid a record $864,253.50. A two-dollar Trifecta brought back $133,134, while the 2-dollar Exacta paid a measly $9,814.
AFLEET ALEX would go on to Win the Preakness after nearly falling at the top of the stretch and then dominate the Belmont.
GIACOMO finished 3rd in the Preakness, 7th in the Belmont, and Won one more Stakes race in 2006 before retiring.
