While learning to play football on the streets, Gaynor was given the nickname Cobra by one of his friends, who just felt like giving him a name.
It was the Bull Bay under fifteen Corner League where his team, Lodge United, was the eventual champion.
In 2003 and 2004 he won the Jamaica High School Alumni Competition in Bronx New York, representing his Alma Mater.
In 1988 Gaynor was awarded a four-year football scholarship in the United States of America at Alderson Broaddus College in Philippi, West Virginia.
In 1983, Gaynor made his big career move at the age of eighteen when he joined neighboring Club Harbour View.
While representing Harbour View with some excellent performance, Gaynor was given the nickname Cabrini, who was the Italian left full back from the 1982 World Cup winning team.
During his tenure as a national player, Gaynor was dubbed by one reporter as "the man who doesn't know how to play a bad game".
The following year Gaynor's Bull Bay team's hard work paid off again when they were awarded the Major League champions.
In 2001, Gaynor transferred from Harbour View and went back to Bull Bay where he becomes a player coach.
He got various colleges to give young football players, both boys and girls from Jamaica, a full four- or two-year scholarship.
The Barrington Gaynor Foundation kept its first Back To School Treat in 2007 at his home in 9 Miles Bull Bay, where they cater for 1,000 children in the community, and this was held again in 2008.
Gaynor was diagnosed with Amyotrophic lateral sclerosis (ALS) or Lou Gehrig's disease in January 2008.
In August 2008 a benefit match featuring George Weah was held for him in New York City.
[6] On 27 February 2011, Gaynor was honoured and handed several donations to facilitate medical expenses while he attended a Jamaica National Premier League match between Harbour View and Boys' Town.