The 1959 pennant-winning season was by far his best in the majors. It included 210 of his 241 career at-bats, as McAnany, a contact hitter with little power, batted .276 for the White Sox with no home runs but just 26 strikeouts.
Called up to the majors in late 1958, McAnany made his MLB debut on September 19, 1958 in Kansas City, pinch-hitting for White Sox pitcher Early Wynn in the fifth inning. He struck out against Ralph Terry and ended up a hitless 0-for-13 for the '58 season. He then had his breakout season in 1959, becoming an integral part of a Sox team that captured the American League pennant for the first time since 1919.
After the Sox won Game 1 of the World Series with the Los Angeles Dodgers 11–0, McAnany started in right field for Game 2 against Dodger left-handed pitcher Johnny Podres. He went 0-for-3 as the Sox, after taking a 2–0 lead, lost the game 4–3.
In baseball's 1960 expansion draft, the new Los Angeles Angels franchise claimed McAnany with the 49th pick. He was then traded on April 1, 1961 to the Chicago Cubs in exchange for Lou Johnson. Hampered by injury, he had 16 at-bats as a Cub and 12 in the minors before retiring in 1963.
McAnany was mentioned in Jane Leavy's 2010 book The Last Boy: Mickey Mantle. In it is a story in which McAnany was hit by a Mickey Mantleline drive during the 1959 season and stated, "I think I have a hole in my chest."[citation needed]
According to a Chicago Tribune column of Oct. 21, 2005 by Mike Downey, McAnany, employed by an insurance agency in Southern California, returned to Chicago to participate in a "Turn Back the Clock" weekend sponsored by the White Sox in June 2005 when the Los Angeles Dodgers played at Comiskey Park for the first time since the '59 World Series. Four months later, the White Sox would return to the World Series for the first time in 46 years.