Jesse Winker competed at Cooperstown Dreams Park twice, both times with the Central Florida Express (FL). His first trip was Tournament 1 in 2004 when the team won the Around the Horn skill competition with a time of 27.13 seconds, Jesse posted a 4th place finish in the Golden Arm, and the team reached the Sweet 16. The second trip was Tournament 5 in 2006. Jesse helped his team to an undefeated record in pool play for the top seed and reached the championship game where they fell to the Houston Heat, 9-5.

Jesse graduated from Olympia High School (Orlando, FL). The outfielder committed to playing baseball at the University of Florida (Gainesville, FL), however, he decided to go professional when the Cincinnati Reds selected him in the 2012 Major League Baseball draft. Jesse made his Major League debut on April 14, 2017.

Jesse was traded to the Seattle Mariners prior to the 2022 season then moved to the Milwaukee Brewers following the same season. In February of 2024, he went to the Washington Nationals until the New York Mets acquired him on July 28, 2024. Jesse helped the Mets reach the 2024 National League Championship Series where they fell to the Los Angeles Dodgers in six games.