Headliner (foaled March 17, 2022) is an active Thoroughbred racehorse, best known for winning the Trinidadian Triple Crown in 2025. He was undefeated for two starts in 2024, including the Grade 2 First Citizens Juvenile Championship. He maintained his winning streak for five more starts during 2025, consecutively winning three Grade 1s in the Guineas, Midsummer Classic, and Trinidad Derby, completing the Trinidadian Triple Crown undefeated.
Headliner is a chestnut colt with a white star and strip that widens to the left side of his nose. He has one white pastern on his back left leg. He races in the Canary colors of his owner, Diane Scott, and is trained by John O'Brien.
Headliner's sire, Headline News, is notable for defeating multiple time Jamaican Horse of the Year Bigman In Town twice, once in the Gold Cup Grade 1 and once in the Starlight Stakes; Headline News also won the Grade 1 Champagne Stakes in 2014. Headline News is sired by Silver Train, a Breeders' Cup Sprint (2005) winner. Headline News' other notable progeny include Making Headlines, In The Headlines, and Headlines Again; Headliner's full sister, In The Headlines, completed the Triple Crown two years prior in 2023, being similarly undefeated during the achievement.
Headliner's dam, B's Passion, won the graded Oaks Stakes and Royal Colours Classic, being Grade 2 and Grade 3 events respectively. She is sired by Precise Sweep, a son of End Sweep, the winner of the Jersey Shore Breeders' Cup Stakes in 1994.
On November 30, 2024, Headliner debuted with The Native Bred 3 Y.O Maidens, at Arima Race course, covering 1100 meters. Jockeyed by Dillon Khelawan, Headliner was out of the gate slow, but won by a length. His next race was the 1350 meter Grade 2 First Citizens Juvenile Championship on December 26, 2024. He was once again ridden by Khelawan, and won by two and a half lengths.
His first race of the year was with the 2000 meter Modified Benchmark 3 Y.O & Over (45-30), on January 25. Headliner lead the pack until the end, leading by six lengths, but ultimately finishing by four. After his three-year-old debut, he was onto the 1600 meter Chief Commander Classic on March 29. He maintained a four length lead throughout the race, winning the race with a four and a third length gap between him and second placer Showtime. His trainer, John O'Brien was not surprised by his win, saying, "The Commander Classic was won by Headliner, who we all expected to run very well, as he has been unbeaten so far. He did perform really well, and won by four or five lengths."
After the Chief Commander Classic, the next goal was the Trinidadian Triple Crown. The first jewel was the Guineas on May 30, an 1800 meter race; Starting on the outside in post seven, the final ruling was Headliner first by ten lengths and a third, with Free Pass in second and Valante in third. The final running time was 1:58.10. Jockey Dillon Khelawan said about the colt's "exceptional" performance in the Guineas, "I thought that coming to the corner I should expect some challenges but that did not happen, [...] Headliner just kept up the gallop all the way up the straight. That is how classy he is."
On August 1, Headliner ran in the Midsummer Classic, another 1800 meter race, and the second of the Triple Crown races. 1/9 in the betting, Headliner took first by six and a forth lengths. Trainer John O'Brien said that it would "Take a super-performance by another three-year-old to stop him from winning [The Derby]." Following the Midsummer Classic, on September 24 Headliner went on to win the Trinidad Derby, the final leg of the Trinidadian Triple Crown. He finished the race twelve lengths and a half over second place colt Have A Great Day.
Headliner was jockey Khelawan's first Triple Crown success; Khelawan said that the colt had shown "Remarkable improvement", and he had "Never doubted [Headliner] would win the Triple Crown".
On December 6 Headliner ran in the Stewards Cup, placing second to Hello World by five lengths, making the race his first loss in his career.
The data below has been sourced from Trinidad and Tobago Racing Authority, and the Arima Race Club Official Website.
Source: