Shackleford, winner of the Preakness Stakes this spring, held on for third. Longshot Tres Borrachos added value to the trifecta.
Shackleford took over the lead from pacesetting The Factor at the end of the run down the backstretch and appeared to have the advantage. But when jockey Rajiv Maragh booted Caleb's Posse into gear well out in the middle of the track, he quickly closed to the lead and drew off to win by 4 lengths.
"The last sixteenth, we just got to celebrate," said winning trainer Donnie Von Hemel.
Caleb's Posse, a 3-year-old, Kentucky-bred colt by Posse, finished in 1:34.59 over a fast track.
Earlier in the year, he was on the Kentucky Derby trail before finishing 12th in the Arkansas Derby. After that race, he took a break, then won the Ohio Derby at Thistledown and the Amsterdam and King's Bishop at Saratoga. In the latter race, he beat Uncle Mo by a nose.
In his last start before the Breeders' Cup, however, Caleb's Posse finished third in the Indiana Derby, a race in which Shackleford finished second.
Caleb's Posse now has won half of his 16 lifetime starts.