Jesse Cleveland

Graduated 1975 – Winter Park Sports Hall of Fame Class of 2010

Coach Bobby Marr says of Jesse Cleveland, “He was one of the top four basketball players ever to play at Winter Park.”

Jesse was a member of the Wildcat basketball team that was State Championship Runner-Up in 1974. He was a part of the “Darrell Dawkins Era” which marked one of the biggest rivalries in Winter Park basketball history and was a major factor in the Cats’ success against the formidable Evans Trojans.

During Jesse’s three years as a Wildcat center, he was named All-Metro, All-District, All-Region, and All-State, earning him a place in the 1974 All-State Basketball Tournament. His junior year Jesse was the leading rebounder and set the school record for rebounds. During his senior season, Jesse was one of the varsity basketball team captains and was selected as team. In addition to his basketball honors, Jesse also lettered in track and field as a senior.

Jesse began his college career at the University of Southwestern Louisiana in Lafayette on a basketball scholarship before transferring to Mississippi Valley State University. While at Mississippi Valley, he was selected as team captain for both his junior and senior years, finished as most improved player, and received Southwestern Athletic Defensive Team honors.

Returning to Winter Park after graduation, Jesse spent a year with the Sheriff’s Department before transferring to the Corrections Division where he served for 24.5 years before retiring with the rank of Captain.

Jesse is married to his college sweetheart Rosie. They have three children, Alternese, Yolanda, and Jeffery and are expecting their sixth great-grandchild in November.

Of his years at Winter Park Jesse says, “It was the most fun time of my life, attending such a highly regarded school of champions which helped me prepare for life.”