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Piersall became a professional at age 18, signing a free agent contract with the Boston Red Sox in 1948. He would reach the majors in 1950, playing in six games as one of the youngest players in baseball. In 1952 he earned a more substantial role with the Red Sox. The young outfielder frequently referred to himself as "The Waterbury Wizard", a nickname which was not well-received by teammates.
It was at this time that Piersall's mental condition began to deteriorate, culminating in an on-field nervous breakdown. Piersall immediately entered treatment and would not return that season. According to his autobiography, Piersall blamed much of his condition on his father, who placed excessive pressure on him to succeed as a baseball player as a small child. Nevertheless, not only would Piersall return to baseball by the opening of the 1953 season, but he finished ninth in voting for the MVP Award. The next year he became the Red Sox's regular center fielder, taking over for Dom DiMaggio and playing well enough to remain a fixture in the starting lineup through 1958. Piersall was selected to the American League All-Star team in 1954 and 1956, and his consistently solid outfield play (which earned favorable comparisons to Joe DiMaggio) earned him a Gold Glove Award in 1958. Piersall was then traded to the Cleveland Indians, with whom he earned a second Gold Glove in 1961. After that season, he was traded to the Washington Senators where his career began to decline. He would play in a backup role for the New York Mets and the Angels before his retirement in 1967.
In a 17-season career, Piersall was a .272 hitter with 104 home runs and 591 RBI in 1734 games. His most productive season came in 1956 with the Red Sox, when he posted a league-leading 40 doubles and 156 games played with 91 runs, 87 RBI, and a .293 batting average. In 1957 he collected 19 home runs and 103 runs. For the Indians, Piersall hit .282 with a career-high 18 steals in 1960, and finished third in the batting race in 1961 with a .322 average, behind Detroit Tigers Norm Cash (.361) and Al Kaline (.324).
Piersall dealt with his illness and notoriety with an affable, jovial disposition and occasionally eccentric on-field behavior. He once played a game in a Beatles wig, led cheers for himself in the outfield during breaks in play, "talked" to Babe Ruth behind the center field monuments at Yankee Stadium, and ran the bases backwards after his 100th home run. His attitude towards his illness can be summed up in a quote from his autobiography –"Probably the best thing that ever happened to me was going nuts. Whoever heard of Jimmy Piersall, until that happened?"
Piersall later had a broadcasting job with the Chicago White Sox from 1977 to 1981, and was teamed with Harry Caray, but was ultimately fired after excessive on-air criticism of team management. He became the subject of a movie based on Piersall's writings, Fear Strikes Out, where he was portrayed by Anthony Perkins (directed by Robert Mulligan, 1957). While still highly regarded for its merits as a film, Piersall would eventually disown the film due to its distortion of the facts. The film, and Piersall's life, are frequently cited today as cautionary tales for parents who pressure their children to succeed in youth sports. Besides Fear Strikes Out, Piersall authored The Truth Hurts, in which he details his ouster from the White Sox organization. Piersall, who winters in Arizona and still does a sports radio show in Chicago, was delighted to receive an invitation to White House event honoring the 2004 World Champions Boston Red Sox on March 2, 2005. According to a Sox official, the White House prepared a guest list of about 1,000 for the event, scheduled to be staged on the South Lawn. "This is a real thrill for a poor kid from Waterbury, Connecticut," Piersall said. "I'm 75 years old. There aren't many things left". He also said he visited the White House once before as guest of President John F. Kennedy.
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