Lester Leroy "Wimpy" Caywood (August 18, 1903 – February 4, 1986) was an American football player from Sapulpa, Oklahoma. Caywood played professionally in the National Football League (NFL) as a guard and tackle.
Caywood made his National Football League debut with the Buffalo Rangers in 1926. Over the next nine season he played for the Cleveland Bulldogs, Cincinnati Reds, St. Louis Gunners, Detroit Wolverines, Brooklyn Dodgers, Pottsville Maroons, Chicago Cardinals and the New York Giants, where he was a part of the Giants 1927 NFL Championship team. He also was a member of the Kansas City Cowboys in 1926, although he never actually played in a game with the team.