About Brett Callaghan

Thoroughbred Horse Racing Jockey

  • How I got involved in horse racing?
  • Where did I race?
  • Racing Accidents
  • Jockey Profile
  • North American Racing Statistics
  • compliments of Equibase.com
  • Back to School
  • Working at CIBC Mortgages Inc.
  • Return to Barbados
  • Barbados Island Guide
  • Totally Barbados Real Estate
  • Totally Toronto
At the age of ten years old, while returning from primary school with my Mom, I told her of how the kids were calling me names such as “shorty,” “smurf,” “midget,” “pip-squeak,” etc… while in tears.
Now, to give you an idea of how short and lightweight I was, imagine how small I was, if at the age of fourteen my body weight was only 66 lbs? How much shorter was I four years younger?
In trying her best to console me, my Mom suggested that as my older brother Slade had wanted to become a jockey but was told he might be too heavy and much taller; that “maybe” if I started learning how to ride horses, that I could one day be a jockey.
The next week, I began equestrian riding at Big C Stables to be a professional thoroughbred jockey.As I turned fourteen years old, while weighing only 66 pounds and was merely four foot, seven inches tall,  I applied and received my exercise jockeys license at the Garrison Savannah in Barbados.

I rode racehorses on mornings at the Garrison Savannah racetrack in Barbados for twelve months from 6 am – 8 am, before dressing in the jocks room and going to school five days a week while exercising as much as I could on weekends.

Apprentice Jockeys License

At the age of fifteen, Darren Fortune and I applied for and successfully received our apprentice jockeys license by jumping out of the starting gates.

I then took part in and rode my first professional race in November 1989 at the Garrison Savannah in Barbados, following my older brother’s footsteps who had already been racing for a few years.

I won 34 races in Barbados from 388 rides from period of November 1989 to March 1993.

Racing in Trinidad and Martinique

I also rode ten races in Martinique in those years, with one winner, and 14 rides in Trinidad with two winners. They race about 25 times a year in Barbados, as the horse population is pretty small. But, it is a great track to learn a lot of the basics of race riding.

Racing Accidents

During those years, I was off for four months due to an accident that happened just after a race, as the horse fainted (while I was still aboard) while galloping out.
I was in a coma for two weeks, but thank God I made a complete recovery, with no lasting side effects.
Nevertheless, I continued racing as it is a great love of mine, in four months, two months earlier than the Doctors expected. On my first ride back, I finished 3rd on one of my favorites, “Man’s Wish,” which I won 7 races on during my Barbados career.

Racing in Canada

In 1993, I moved to Toronto, Canada, to further pursue my racing career at Woodbine (www.woodbineentertainment.com), Fort Erie (www.forterieracing.com) Greenwood racetracks in Ontario region of Canada.

In Canada, I’ve ridden in over 1,200 races with a total of 135 wins (As of September 21st, 1998), mostly at Woodbine, Fort Erie, and Greenwood racetracks. In all, I have ridden 174 winners (As of November 17th, 1998).

Career Statistics in North America:
Starts: 1,503
Firsts: 135
Seconds: 166
Thirds: 199
Earnings: $2,084,172
Avg. Earnings Per Start: $1,387

Year Starts Firsts Seconds Thirds Earnings
1998 52 7 6 5  $106,233
1997 236  20 21 37  $270,433
1996  119  9 19 14  $150,853
1995 344  36 43 42  $574,394
1994 236 17 26  32  $280,759
1993  516  46 51  69 $701,500

See Racing Stats for Jockey Brett Callaghan at Equibase for North America Racing.


I was also off for five months in 1996 due to an operation I had to have on my knees due to a cyst in one knee and a chipped bone in the other, all wear and tear from racing.

I then decided to place my racing career on ‘HOLD’ for the remainder of 1998, to take a Microsoft Skills 2000 computer Course (Microsoft Certified Systems Engineer Course). This course required full-time participation for five days a week, for five months or 21 weeks (June 22nd – November 13th ’98).

Needless to say, since completing the program by sitting and passing all 6 of the Microsoft Exams, I am now a “Microsoft Certified Systems Engineer (MCSE).

During my studies, I continued exercising racehorses at the racetrack (Woodbine) on weekends. During these months, I continued to ride in three-horse races at Woodbine (Up to November 17th, ’98) on a horse from my homeland in Barbados, racing in Toronto since 1997.

His name is “Incitatus,” who also won the 1997 Gold Cup in Barbados. Out of those three rides on him, I’ve managed to get a win, a third, and a fifth; pretty well indeed for an ex-jockey!

I decided to take this opportunity while I was still young (24 years) as a means of “having something to fall back on” in case my racing career does not work out to be beneficial in the long run !!!!!!!! I’m proud of my decision to go back to school and am extremely happy about my decision to retire entirely from racing (February 2004).

Since February 1999, I’ve been working at CIBC Mortgages Inc. in Toronto as a Senior Technical Analyst and have thoroughly enjoyed the learning experience in the business sector of Toronto.

In March 2005, I decided to return to Barbados, my homeland, to begin a project called Totally Barbados. This project is designed to promote all of the incredible beauty of the Barbados Tourism Product.

Read all about my success Barbados Island Guide – Totally Barbados.

I developed and launched Totally Barbados Real Estate in October 2008 to help real estate agents and brokers and individuals sell and rent property in Barbados.

In 2010 I then began another project of mine, called Totally Toronto. This site was launched on November 19th, 2010, and is designed to encourage tourism in Toronto.

Other sites and projects have included:

  1. Barbados To Do, Mobile Apps, and Email Guide.
  2. Sell It Barbados, the place to list, buy or sell used items.
  3. Barbados Web Design for all of your web development and management.
  4. Totally Barbados Events Calendar Guide
  5. Totally Toronto City Guide