Brett Callaghan

Last Updated: January 31, 2026

Jockey Brett Callaghan: Horse Racing Profile and Career Overview

Who Is Brett Callaghan, and Early Racing Exposure

Brett Callaghan is a retired professional jockey whose racing career spanned nearly a decade across Barbados, Trinidad, Martinique, and Canada. He rode professionally from November 1989 through July 1998 and competed at major Canadian racetracks, including Greenwood, Woodbine, and Fort Erie, while also building early experience in the Caribbean.

Brett Callaghan grew up in a racing environment and followed his older brother, Slade Callaghan, into the profession. The two brothers rode professionally in both Barbados and Canada, forming a rare sibling presence across international racing circuits. Their careers developed through daily exposure to race riding rather than shortcuts, with emphasis on balance, timing, and judgment learned in competitive jockey colonies.

Brett Callaghan began riding professionally on November 18, 1989, at the Garrison Savannah racetrack in Barbados. His first career ride came aboard Simply Red for trainer Bill Marshall. Early Caribbean racing demanded adaptability and patience, and those skills carried forward as he expanded his career beyond Barbados.

By his seventh career ride, Brett Callaghan secured his first professional victory aboard Edgewater. That early win confirmed his ability to compete under race-day pressure and marked the beginning of a career built on steady opportunity rather than publicity.

Before arriving in Canada, Brett Callaghan recorded verified wins in multiple jurisdictions. He won 34 races in Barbados, two in Trinidad, and one in Martinique. Those results established him as a capable rider before entering the Canadian racing system.

Career Highlights

First career race
Date: November 18, 1989
Track: Garrison Savannah, Barbados
Horse: Simply Red
Trainer: Bill Marshall

First career win
Career ride number: Seventh
Horse: Edgewater
Date: Verified early career sequence

First Canadian race
Date: April 9, 1993
Track: Greenwood Racetrack
Race: Race 7, Claiming
Horse: Chili Lee
Finish: 10th

First Woodbine ride and win
Date: April 28, 1993
Track: Woodbine Racetrack
Race: Race 6, Claiming
Purse: CAD $16,600
Horse: Pleasant Courtney
Finish: 1st

Most recent race
Date: August 8, 1998
Track: Woodbine Racetrack
Race: Race 9, Allowance
Purse: CAD $33,600
Horse: Incitatus (BAR)
Finish: 3rd

Career scope
Professional jockey from November 1989 through July 1998
Raced in Barbados, Trinidad, Martinique, and Canada

Verified win totals by jurisdiction
Barbados: 34 wins
Trinidad: 2 wins
Martinique: 1 win
Canada: 135 wins at Greenwood, Woodbine, and Fort Erie

Canadian seasonal win totals
1993: 46 wins
1994: 17 wins
1995: 36 wins
1996: 9 wins
1997: 20 wins
1998: 7 wins

Steward note
Since October 9, 2021, Brett Callaghan has served as a racing official and Steward at the Garrison Savannah racetrack in Barbados.

Statistical note
Complete Equibase earnings totals from the early 1990s era remain incomplete. This profile prioritizes verified race records, win counts, and documented seasonal performance.

The Move to Canada and Entry Into Ontario Racing

Brett Callaghan entered Canadian racing in the spring of 1993. His first Canadian ride came on April 9, 1993, at Greenwood Racetrack aboard Chili Lee in a claiming race. Although the result placed him tenth, the start marked his formal entry into one of the most competitive jockey colonies in the country.

Less than three weeks later, Brett Callaghan made his Woodbine debut and won immediately. On April 28, 1993, he guided Pleasant Courtney to victory in a claiming race worth CAD $16,600. Winning on a first Woodbine mount established early credibility with trainers, racing officials, and the racing office.

Fort Erie followed shortly after. Brett Callaghan’s first three rides at the track resulted in wins, although the first victory was disqualified. He responded the same day with two official wins, demonstrating composure and professionalism under review.

The 1993 Season That Defined His Canadian Career

The 1993 season became the most productive year of Brett Callaghan’s Canadian career. He recorded 46 wins across Greenwood, Woodbine, and Fort Erie, including 37 wins at Woodbine and seven at Fort Erie.

Those results reflected consistent daily production rather than isolated success. Brett Callaghan won aboard a wide range of horses and for multiple trainers, a key indicator of trust within a competitive jockey colony.

The season established him as a reliable professional rider capable of delivering results across tracks and conditions.

Sustained Riding Through the Mid-1990s

From 1994 through 1997, Brett Callaghan continued to ride actively across Ontario. His win totals reflected the natural rhythm of professional race riding.

1994 produced 17 wins.
1995 followed with 36 wins, marking his second strongest season numerically.
1996 resulted in nine wins after he missed four months due to surgery on both knees.
1997 closed with 20 wins.
1998 closed with 7 wins.

These seasons reflected steady participation in a demanding environment where mount availability, trainer relationships, and racing office decisions shift continuously.

Riding Risks and Career Challenges

Thoroughbred horse racing carries inherent risk. Brett Callaghan experienced his first fall early in his career at the Garrison Savannah in Barbados. The incident was documented through a series of race photographs and reinforced the profession’s physical realities.

He continued riding through physical setbacks without allowing injury or adversity to define his career trajectory. No career-ending injury forced retirement. Brett Callaghan stepped away from race riding on his own terms.

Final Rides and Closing the Career at Woodbine

Brett Callaghan’s final rides came in 1998 at Woodbine aboard the Barbadian-bred Incitatus for Barbadian-born trainer Ronald G. Burke. That partnership carried personal and professional significance.

His final three recorded rides were:

July 1, 1998, Woodbine
Race: Optional Claiming
Purse: CAD $33,100
Horse: Incitatus (BAR)
Finish: 1st

July 19, 1998, Woodbine
Race: Twist the Snow Handicap
Purse: CAD $48,000
Horse: Incitatus (BAR)
Finish: 5th

August 8, 1998, Woodbine
Race: Allowance
Purse: CAD $33,600
Horse: Incitatus (BAR)
Finish: 3rd

The final win closed the career with intention rather than decline.

Life After Race Riding

Brett Callaghan retired from professional race riding in 1998. Following retirement, he transitioned into digital work and promotion rather than remaining in the saddle.

From 1999 to 2005, he worked in Toronto, Canada, including time at CIBC Mortgages Inc. He returned to Barbados in 2005 and founded Totally Barbados – Barbados Island Guide, a long-running digital platform that promotes Barbadian businesses, culture, tourism, and community initiatives.

Since October 9, 2021, Brett Callaghan has served as a racing official and Steward at the Garrison Savannah racetrack in Barbados. His background as a former professional jockey provides practical insight into race dynamics, rider decision-making, and safety considerations, contributing to informed and balanced officiating.

Why Brett Callaghan Matters to Canadian Racing History

Brett Callaghan represents a generation of riders who moved fluidly between Barbados and Canada, built reputations through daily work, and contributed meaningfully to Canadian racing during a competitive era.

He won races at Greenwood, Woodbine, and Fort Erie. He rode internationally. He retired on his own terms. He later returned to the sport as a racing official and steward.

That full-circle involvement gives his career lasting relevance within Canadian thoroughbred racing history.

Frequently Asked Questions

Q1: Who is Brett Callaghan
Brett Callaghan is a retired professional jockey who rode from 1989 through 1998 in Barbados, Trinidad, Martinique, and Canada, including Greenwood, Woodbine, and Fort Erie.

Q2: When did Brett Callaghan begin his riding career
He began riding professionally on November 18, 1989, at the Garrison Savannah in Barbados.

Q3: When did Brett Callaghan first ride and win in Canada
His first Canadian ride came on April 9, 1993, at Greenwood. His first Woodbine ride and win came on April 28, 1993.

Q4: How many wins did Brett Callaghan record in Canada
He recorded most of his career wins in Canada, including 46 in 1993 and consistent production through 1998.

Q5: When did Brett Callaghan retire from riding
He retired from professional race riding in July 1998.

Q6: Is Brett Callaghan still active in horse racing
He has retired from race riding. He currently serves as a racing official and Steward at the Garrison Savannah in Barbados and remains involved in racing through media, promotion, and historical documentation.

This article was enhanced using AI tools for drafting, but was thoroughly reviewed and edited by our team of experts at Jockeys Canada.

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