[2] Born in Havana, Arkansas, Sain pitched for 11 years, winning 139 games and losing 116 in his career and compiled an earned run average of 3.49.

His best years were those immediately after World War II, when he won 100 games for the Boston Braves, before being traded to the New York Yankees during the 1951 season for Lew Burdette and cash.

In 1943, while participating in a benefit game for the Red Cross, Sain became the last man to pitch against Babe Ruth in organized baseball.

[5] That year, the Boston Braves won their second, latter National League pennant of the post-1901 era, but fell in six games to the Cleveland Indians in the 1948 World Series.

Sain won the first game of the Series, a 1–0 shutout at Braves Field that included a memorable play in which Boston catcher Phil Masi was called safe after an apparent pickoff at second base.

With the Yankees, Sain became a relief pitcher and enjoyed late-career success, leading the American League in saves with 22 in 1954.

After retiring as a player, Sain spent many years as a well-regarded and outspoken pitching coach for the Oakland Athletics, New York Yankees, Minnesota Twins, Detroit Tigers, Chicago White Sox and Atlanta Braves.

While serving as the Yankees pitching coach, Sain picked up an apple one day and poked a broken car antenna through it.

[7] An independent thinker among coaches, Sain tended to be admired by his pitchers, although he battled with at least two of his managers—Sam Mele of the Twins and Mayo Smith of the Tigers—when he disagreed with them.

Sain did not make friends among owners and general managers, either, when he would advise pitchers to "climb those golden stairs" to their teams' front offices to demand more money in salary talks.

"[8] Jim Bouton, in his book Ball Four, expressed unreserved admiration for Sain, who had been his pitching tutor in New York during his first two Major League seasons, 1962 and 1963.