Weakly began competing in athletics (Track and field) at St. Elizabeth Technical High School.

After graduation Weakly attended Southwestern Christian College where he won both silver and bronze at the 1994 & 1995 NJCAA National Championships.

[1] Also during his time at Southwestern Christian College Weakly qualified for the 1994 Commonwealth Games final where he finished eighth.

Weakly then transferred to George Mason University being a part of the 1995 Indoor National Championship winning team.

Later that year he would sign a professional contract with Nike.Weakly is best known for winning the gold medal in the 400m hurdles at the 2001 Jamaican Athletics Championships.