Jack McDowell was drafted by the Boston Red Sox in the 20th round of the 1984 amateur draft, but did not sign and instead chose college. After attending Stanford University(Stanford won the College World Series in 1987), McDowell was drafted by the Chicago White Sox in the first round (fifth pick) of the 1987 amateur draft and made his Major League debut on September 15, 1987.
By the early 1990s, he had established himself as one of the most dependable pitchers in the game, pitching effectively and recording over 250 innings each season from 1991 to 1993. Jack won 20 games in 1992 and 22 in 1993, when he won the American LeagueCy Young Award and led the White Sox to the postseason (they lost in the American League Championship Series to the Toronto Blue Jays). From 1988 until 1995, his season ERA was consistently between 3.00 and 4.00, well below the league average . In 1993, he set a modern (post-1950) record by recording a decision in each of his first 27 starts.
After the 1994 season McDowell was traded to the New York Yankees for minor league pitcher Keith Heberling and outfielder Lyle Mouton. McDowell spent one rocky season in New York with the Yankees and put up decent numbers, but was perhaps best known for giving the finger to the fans at Yankee Stadium after being booed off the field after getting bombed by the White Sox on July 18, 1995 in the second game of a doubleheader. McDowell was also the pitcher who gave up the walk-off, series-winning hit to Edgar Martínez in Game 5 of the 1995 American League Division Series, scoring Joey Cora and Ken Griffey, Jr. to eliminate the Yankees from the playoffs and send the Seattle Mariners to the American League Championship Series.
McDowell struggled over his final seasons, starting in 1996, and eventually retired in 1999. During this time he played for the Cleveland Indians and Anaheim Angels.
Even during his baseball career, McDowell played guitar in various groups in the alternative rock genre, usually performing during the baseball off-season.
McDowell's band, Stickfigure, was formed in 1992, following a tour with his former band, V.I.E.W., as the opening act for The Smithereens.
In 2008, musicians Scott McCaughey (of The Minus 5), Steve Wynn, Linda Pitmon, and Peter Buck formed The Baseball Project to pay homage to America 's greatest pastime. Their album Volume 1: Frozen Ropes and Dying Quails contains the song The Yankee Flipper, a tribute to their friend Jack McDowell and a confession that a long night of drinking with the musicians may have led to the infamous finger to the crowd.