Born in Denver, Jester threw and batted right-handed and was listed as 5 feet 11 inches (1.80 m) tall and 188 pounds (85 kg).

[1] Jester signed as a free agent in 1947 with the Boston Braves[2] and worked his way through their farm system for 51⁄2 years before being recalled in June 1952.

After seven appearances as a relief pitcher, he received his first starting assignment in the second game of a doubleheader on July 13 against the cellar-dwelling Pittsburgh Pirates.

Jester threw a complete game, 2–1 victory at Forbes Field, allowing seven hits and three bases on balls, with three strikeouts.

He never returned to the majors, playing in the Braves' system through 1954 and then, after a four-year hiatus, getting into 14 games with the 1959 Denver Bears of the Triple-A American Association.