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 1 races in the Guineas, Midsummer Classic, and Trinidad Derby, completing the Trinidadian Triple Crown while undefeated.

Background 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 another Grade 1 in the 2014 Champagne Stakes. 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, also 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, a successful American sire who won the Jersey Shore Breeders' Cup Stakes in 1994.

Racing career

2024: Two-year-old Season On November 30th, 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 26th, 2024. He was once again ridden by Khelawan, and won by two and a half lengths.

2025: Three-year-old Season His first race of the year was with a 2,000 meter modified benchmark on January 25th. Headliner led the pack until the end, leading by six lengths, but ultimately finishing by four. After his three-year-old debut, he was onto the 1,600 meter Chief Commander Classic on March 29th. 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.

After the Chief Commander Classic, the next goal was the Trinidadian Triple Crown. The first jewel was the Guineas on May 30th, an 1,800 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 Valiante in third; The race's final running time was 1:58.10. His jockey, Dillon Khelawan, said about his "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 1,800 meter race, and the second of the Triple Crown races. 1/9 in the betting, Headliner took first by six and a forth lengths. Following the Midsummer Classic, on September 24th 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 went on to say he had "Never doubted [Headliner] would win the Triple Crown".

On December 6th Headliner ran in the Stewards Cup, placing second to Hello World by five lengths, making the race his first loss in his career.

2026: Four-year-old Season After his loss at the Stewards Cup, he was entered in for the Grade 1 Gold Cup on December 26th, however he did not show for the race.

Headliner was then transported to Barbados to run in the Grade 1 Tanglewood Stakes & Trophy, arriving in the country on January 23rd. Despite starting strongly, he fell behind as the race continued, and ultimately placed last among the eleven horse field. Headliner's loss in the Tanglewood Stakes was followed by a three-month stay in Barbados, before returning to Trinidad on March 20th.

On April 6th, Headliner was entered to race in the 1,600 meter Champagne Stakes as his return race; He led the race from start to finish, beating six-year-old Gold Cup shower El Chico Malo by a length in the process.

After a win in the Champagne Stakes, Headliner competed in another 1,500 benchmark race. Similar to his performance in the Tanglewood, he started strongly out the gate, was challenged by Sneaky Cheeky into second, lost speed as the race approached the final furlongs, and placed last for a second time in his career.

Headliner returned to racing three weeks later on June 19th, where he ran in the Grade 3 President's Cup; In an improvement from his last start, he won the 1,900 meter race by fourteen and a half lengths, with The Goddess Nike coming in second. He continued on August 31st to win the Grade 1 Independence Cup, returning a month later to secure another benchmark win.

Racing statistics The data below has been sourced from Trinidad and Tobago Racing Authority, and the Arima Race Club Official Website. DateTrackRaceGradeDistanceHNOddsFinishTime (race time)Loss Margin (win margin)JockeyWinner (Runner-up)2024 – two-year-old seasonNov 30ArimaNative Bred 2 Y.O. Maidens1,100 m21/51:09.4(1)Dillon Khelawan(Valiante)Dec 26ArimaFirst Citizens Juvenile ChampionshipGII1,350 m51/11:25.3(2½)Dillon Khelawan(Marmalade)2025 – three-year-old seasonJan 25ArimaModified Benchmark 3 Y.O. & Over (45-30)1,500 m21/51:36.4(4)Dillon Khelawan(Schwarzenegger)Mar 29ArimaChief Commander ClassicGII1,600 m61/91:39.4(4¾)Dillon Khelawan(Showtime)May 30ArimaGuineasGI1,800 m71/91:58.0(10¾)Dillon Khelawan(Free Pass)Aug 1ArimaMidsummer ClassicGI1,800 m41/9 1:57.4(6¼)Dillon Khelawan(Free Pass)Sep 24ArimaTrinidad Derby StakesGI2,000 m11/52:09.4(12½)Dillon Khelawan(Have A Great Day)Dec 6ArimaSteward's CupGI1,200 m38/5(1:12.0)4¼Ricky JadooHello World2026 – four-year-old seasonFeb 7Barbados TurfXXIII Tanglewood Stakes & TrophyGI2,000 m66/111th(2:09.4)24½Arron DanielPussykatApr 6ArimaChampagne StakesGIII1,600 m28/51:38.4(1)Tristan Phillips(El Chico Malo)May 30ArimaModified Benchmark 3 Y.O. & Over (70+)1,500 m61/56th(1:31.1)2¼Dillon KhelawanThe Goddess NikeJun 19ArimaPresident's CupGIII1,900 m53/52:00.314½Dillon Khelawan(The Goddess Nike)Aug 31ArimaIndependance CupGI1,800 m64/51:51.2 DISTNobel Abrego(Hello World)Sep 24ArimaModified Benchmark 3 Y.O. & Over (70+)1,35031/21:20.44¾Dillon Khelawan(Valiante)

Pedigree Source:

References