“The Heartbreak Kid” finally breaks through

After months of close calls and crushing defeats, Calvin Bailey finally had his day in the sun.

The jockey, affectionately dubbed The Heartbreak Kid, broke a 30-race winless streak on Sunday, August 30, 2026, guiding Crown Chaser to an emphatic 8-length victory in the afternoon’s seventh race at Caymanas Park. It wasn’t just any win. It was redemption.

Bailey’s season has been defined by near-misses. On Thursday, August 6, in the Jamaica Derby, Bailey aboard Maverick looked certain to win with a furlong to go. The commentator even called it “the surprise of the party”. But in the final strides, London Spirit, under Tevin Foster, stormed home to steal it by a nose.

Two weeks later, on Saturday, August 15, racing gave Bailey another shot. The opening race was restricted to jockeys winless since February 15 — a race built for redemption.

Bailey partnered the 3-1 shot Starlight Princess for trainer Omar Williams. She tracked in second, surged to the front entering the straight, and with 1 ½ furlongs to go, the crowd sensed it, the drought was over, but it wasn’t.

Sunday was different. In a three-year-old and up claiming event ($1,000,000–$800,000) over seven furlongs, Bailey was aboard Crown Chaser for trainer Michael Cain Jr.

Calvin Bailey winning aboard Crown Chaser on Sunday, August 30, 2026.Naphtali Junior

Determined to control his own destiny, Bailey broke sharply and aggressively took the lead. Once Crown Chaser established command, it was over. Crown Chaser kept expanding the margin down the stretch, drawing off to win by 8 lengths over Mr Senator (Shaheem Gordon).The time: 1:28.1 with fractions of 24.0, 47.3, 1:14.0.

The win was Bailey’s first of 2026 from 30 attempts. For Cain Jr, it was his fourth winner from 25 starters this year.

What made it poetic was that Crown Chaser is a former Jamaica Derby champion. The same race that broke Bailey’s heart aboard Maverick this year.