Born in Daisy Station, near Winston-Salem, North Carolina, Gentry first pitched in organized baseball as part of the company team when he worked for Hanes Hosiery in Winston-Salem. From 1939 to 1941, he played minor league ball for Landis in the North Carolina State League, Fulton, Kentucky in the Kitty League (where he struck out 167 batters), and Winston-Salem in the Piedmont League.\n', '

In 1942 and 1943, Gentry pitched for the Buffalo Bisons in the International League. Gentry had good speed on his fastball but lacked control. He struck out 80 batters in 1942, but walked 122. Gentry followed in 1943 with the best season of his career. He pitched an 11-inning no-hitter for the Bisons on Easter Sunday and finished the season with 20 wins and a 2.65 earned run average. He led the league in innings pitched (285), strikeouts (184) and walks (143).\n', '

Gentry\'s performance in 1943 won him a promotion to the big leagues in September 1943. He went 1–3 for the Tigers in 4 starts, but lost two games by the score of 1–0. So his 1–3 record could have just as easily been 3–1 with any run support from a Tigers batting order depleted by the war.\n', '

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