A right-handed pitcher, McDowell played for the Chicago White Sox, New York Yankees, Cleveland Indians, and Anaheim Angels of the Major League Baseball (MLB).

[3] After the 1994 season, McDowell was traded to the New York Yankees for minor league pitcher Keith Heberling and outfielder Lyle Mouton.

He was perhaps best known for giving the finger to the fans at Yankee Stadium while being booed off the field after getting bombed by the White Sox on July 18, 1995, in the second game of a doubleheader.

[5] 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.

This, coupled with the emergence of Andy Pettite who became the Yankees' ace the following season, resulted in McDowell becoming a free agent in the offseason.

McDowell's first band, V.I.E.W., which consisted of him and fellow baseball players Lee Plemel and Wayne Edwards, had two albums, Extendagenda and Replace the Mind.

[11] 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 McDowell and a confession that a long night of drinking with the musicians may have led to the infamous finger to the crowd.