Jesse Kirkland

Jesse Kirkland is a native of Bermuda, and grew up sailing there. He attended college in the United States at St. Mary's College of Maryland in southern Maryland, and sailed while a student. Two years prior to the 2012 Summer Olympics in London, Kirkland and his brother Zander Kirkland began training full-time in an attempt to qualify as Bermuda's representatives in the Olympics 49er competition. The 49er, a small two-person racing dinghy, is a relatively new sailing competition for the Olympics, having debuted for the first time at the 2000 Summer Olympics in Sydney, Australia.

At the 2012 World Championships in Croatia at the Sailing Club Uskok, the Kirkland brothers arrived early to gain experience sailing in local conditions. They advanced to the gold fleet after the preliminary qualifying races and later became the first team to secure one of the five remaining Olympic qualifying places that remained at the time after finishing in eighth place out of seventy-four in the final standings. After their success in Croatia, they likewise left early for Weymouth, England in order to get used to local sailing conditions. They finished in 19th place.

Jesse Kirkland (born January 22, 1988) is a Bermudan competitive sailor. Kirkland was involved with sailing from a young age, and sailed in college at St. Mary's College of Maryland. Following college, he and his brother Zander Kirkland began training in an attempt to qualify for the 2012 Olympic Games in London in the 49er event. During the 2012 49er World Championship in Croatia, the brothers finished in the Gold fleet and thereby qualified to represent Bermuda in the 2012 Olympics.