On Thursday, August 6, in the Jamaica Derby, jockey Calvin Bailey aboard Maverick delivered what the racing commentator aptly described as “the surprise of the party.”
With a furlong to go, Maverick looked every inch the winner, yet, in the final strides, London Spirit under Tevin Foster stormed home to snatch victory by the narrowest of margins, a nose.
For Bailey, who had not tasted success all year, the defeat was devastating.
Then came Saturday, August 15. The opening race of the day carried a special condition: only jockeys who had not won since February 15 could ride. It was a race designed to give the winless a chance at redemption. Nine horses lined up, Bailey partnering the 3‑1 shot Starlight Princess for trainer Omar Williams.
From the off, Bailey rode with quiet determination. Starlight Princess tracked the leader, poised in second, before surging to the front entering the straight. With a furlong and a half left, the crowd sensed it, Bailey was finally about to break the drought. The maiden tag was about to be shed, the burden lifted. It did not happen.
On Sunday, August 30, 2026, the Heartbreak Kid finally got his winner.
Riding in the afternoon’s seventh race, a three-year-old and up claiming event ($1,000,000 – $800,000) over seven furlongs, Bailey partnered with the Michael Cain Jr-trained Crown Chaser.
Intent on seizing his own fate, Bailey broke sharply and aggressively snatched the lead early.
Once Crown Chaser established command, the contest turned into a rout. Expanding his advantage with every stride down the stretch, Crown Chaser drew off to win by eight lengths, leaving second-place finisher Mr Senator (Shaheem Gordon) far in his wake.
Crown Chaser stopped the clock in 1:28.1, setting fractions of 24.0, 47.3, and 1:14.0.
The victory marked Bailey’s first win of 2026 after 30 agonizing attempts, while giving trainer Cain Jr his fourth 2026 triumph from 25 starts.
Yet Bailey’s Day extended beyond the statistic sheet. Bailey’s career has been shadowed by the Jamaica Derby, where he once suffered a loss by the narrowest margin imaginable.
That his breakthrough victory came aboard Crown Chaser, a former Jamaica Derby champion, brought an enthralling racing journey full circle, turning lingering heartbreak into a narrative of redemption.
