Headliner (horse)

Headliner
SireHeadline News
GrandsireSilver Train
DamB's Passion
DamsirePrecise Sweep
SexColt
Foaled17 March 2022
CountryTrinidad
ColourChestnut
BreederMrs. Diane Scott
OwnerMrs. Diane Scott
TrainerJohn O'Brien
Record8:7-1-0
EarningsTT ~$21,2872.00
Major wins
First Citizens Juvenile Championship (2024)
Chief Commander Classic (2025)
Guineas (2025)
Midsummer Classic (2025)
Trinidad Derby (2025)
Awards
13th Trinidadian Triple Crown Champion (2025)

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.

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;[1] Headline News also won the Grade 1 Champagne Stakes in 2014.[1] 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.[2]

Headliner's dam, B's Passion, won the graded Oaks Stakes[3] and Royal Colours Classic,[4] 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.[5]

Racing career

2024: Two-year-old Season

On November 30, 2024,[6] 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.[7] 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 the 2000 meter Modified Benchmark 3 Y.O & Over (45-30), on January 25.[8] 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.[9] 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."[10]

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;[11] 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.[12] Jockey Dillon Khelawan said about the colt's "exceptional"[13] 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."[13]

On August 1, Headliner ran in the Midsummer Classic,[14] 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]."[15] Following the Midsummer Classic, on September 24 Headliner went on to win the Trinidad Derby,[16] 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;[17] Khelawan said that the colt had shown "Remarkable improvement", and he had "Never doubted [Headliner] would win the Triple Crown".[18]

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.[19]

Racing statistics

The data below has been sourced from Trinidad and Tobago Racing Authority,[20] and the Arima Race Club Official Website.[21][22][23][24][25][26][19]

Date Track Race Grade Distance HN Odds Finish Time

(race time)

Loss Margin (win margin) Jockey Winner

(Runner-up)

2024 – two-year-old season
Nov 30 Arima Native Bred 2 Y.O. Maidens 1,100 m 2 1/5 1st 1:09.4 (1) Dillon Khelawan (Valiante)
Dec 26 Arima First Citizens Juvenile Championship GII 1,350 m 5 1/1 1st 1:25.3 (2½) Dillon Khelawan (Marmalade)
2025 – three-year-old season
Jan 25 Arima Modified Benchmark 3 Y.O. & Over (45-30) 1,500 m 2 1/5 1st 1:36.4 (4) Dillon Khelawan (Schwarzenegger)
Mar 29 Arima Chief Commander Classic GII 1,600 m 6 1/9 1st 1:39.4 (4¾) Dillon Khelawan (Showtime)
May 30 Arima Guineas GI 1,800 m 7 1/9 1st 1:58.0 (10¾) Dillon Khelawan (Free Pass)
Aug 1 Arima Midsummer Classic GI 1,800 m 4 1/9 1st 1:57.4 (6¼) Dillon Khelawan (Free Pass)
Sep 24 Arima Trinidad Derby Stakes GI 2,000 m 1 1/5 1st 2:09.4 (12½) Dillon Khelawan (Have A Great Day)
Dec 6 Arima Steward's Cup GI 1,200 3 8/5 2st (1:12.0) Brian Boodramsingh Hello World

Pedigree

Source:[27]

Pedigree of Headliner (TT), chestnut colt, 2022
Sire
Headline News (TRI)
b. 2010
Silver Train (USA)
d.b. 2002
Old Trieste (USA) A.P. Indy (USA)
Lovelier Linda (USA)
Ridden In The Stars (USA) Cormorant (USA)
Shelter Strait (USA)
IGOTASPELLONU (USA) Grand Slam (USA) Gone West (USA)
Bright Candles (USA)
Dutchess Mojo (USA) Deputy Minister (CAN)
Blissful (USA)
Dam
B's Passion (TRI)
dk. b. 2008
Precise Sweep (USA)
dk. b. 1999
End Sweep (USA) Forty Niner (USA)
Broom Dance
Precisely (USA) Summing (USA)
Crisp N' Clear (USA)
Flying Millie (JAM) Sir Lal Bahadur (CAN) Vice Regent (CAN)
Forleana (CAN)
Flying Mal (USA) Aeronaut (USA)
My Gal Mal (USA)

References

  1. ^ a b "Headline News not good at all". www.guardian.co.tt. A commanding victory over Bigman in Town in the Republic Bank Gold Cup was followed by a thrashing of his rivals this year in the Caribbean Turf Championship, the Starlight Stakes, the Champagne Stakes and the Carnival Messiah Stakes. He defeated Bigman in Town for a second time in the Starlight Stakes and some of the best imported turf stayers in the Champagne Stakes. One could not help but get the impression that this colt was still improving and the sky was the limit in terms of what he could have achieved.
  2. ^ "In The Headlines wins Derby and Triple Crown". www.guardian.co.tt. Retrieved 2026-02-21.
  3. ^ "Oaks stakes (Fillies - 3 y.o. w.i. bred)" (PDF). www.ttra.net.
  4. ^ "Royal colours classic (gr. III) nominated 3 y.o. creoles" (PDF). www.ttra.net.
  5. ^ "Equibase". www.equibase.com. Retrieved 2026-02-21.
  6. ^ "Raceday 12 – Saturday, November 30th 2024 – Race 3 Track Sloppy Turf Off – Arima Race Club". Retrieved 2025-12-09.
  7. ^ "Raceday 13 – Thursday, December 26th 2024 – Race 3 – Arima Race Club". Retrieved 2025-12-09.
  8. ^ "Raceday 01 – Saturday, January, 25th 2025 – Race 6 Turf Good – Arima Race Club". Retrieved 2026-01-02.
  9. ^ "Raceday 03 – Saturday, March 29th 2025 – Race 6 – Arima Race Club". Retrieved 2025-12-09.
  10. ^ Walcott, Roneil (2025-04-03). "Champion trainer O'Brien lines up Champagne Stakes after Chief Commander win". Trinidad and Tobago Newsday. Retrieved 2025-12-09.
  11. ^ "Raceday 05 – Friday, May 30th 2025 – Race 5 – Arima Race Club". Retrieved 2025-12-09.
  12. ^ Arima Race Club (2025-05-30). Arima Race Club - Day 5 May 30th 2025 Race-5. Retrieved 2025-12-09 – via YouTube.
  13. ^ a b "Headliner won as he liked". www.guardian.co.tt. Retrieved 2025-12-09.
  14. ^ "Raceday 07 – Friday, August 01st 2025 – Race 7 – Arima Race Club". Retrieved 2025-12-09.
  15. ^ "Headliner wins second jewel impressively". www.guardian.co.tt. Retrieved 2025-12-09.
  16. ^ "Raceday 09 – Wednesday, September 24th 2025 – Race 6 – Arima Race Club". Retrieved 2025-12-09.
  17. ^ "Khelawan first Triple Crown success". www.guardian.co.tt. Retrieved 2026-01-02.
  18. ^ "Khelawan first Triple Crown success". www.guardian.co.tt. Retrieved 2025-12-09.
  19. ^ a b "Raceday 11 – Saturday December, 06th 2025 – Race 5 Track: Wet-Fast – Arima Race Club". Retrieved 2026-01-02.
  20. ^ "HorsesInfo". www.ttra.net. Retrieved 2025-12-10.
  21. ^ "Raceday 12 – Saturday, November 30th 2024 – Race 3 Track Sloppy Turf Off – Arima Race Club". Retrieved 2025-12-11.
  22. ^ "Raceday 13 – Thursday, December, 26th 2024 – Race 3 Track Fast Turf Good – Arima Race Club". Retrieved 2026-01-02.
  23. ^ "Raceday 01 – Saturday, January, 25th 2025 – Race 6 Turf Good – Arima Race Club". Retrieved 2025-12-11.
  24. ^ "Raceday 03 – Saturday, March, 29th 2025 – Race 6 Track: Fast Turf: Firm – Arima Race Club". Retrieved 2025-12-11.
  25. ^ "Raceday 05 – Friday May, 30th 2025 – Race 5 Track: Sloppy Turf: Off – Arima Race Club". Retrieved 2026-01-02.
  26. ^ "Raceday 09 – Wednesday September, 24th 2025 – Race 6 Track: Sloppy – Arima Race Club". Retrieved 2026-01-02.
  27. ^ "Headliner Horse Pedigree". www.pedigreequery.com. Retrieved 2025-12-10.