He made his Major League debut with the Orioles in 1991, and played his first full season with the team in 1992. While with the Orioles, he was a five-time All-Star selection, and a four-time Gold Glove winner. He signed with the New York Yankees in 2001 and continued to play excellent ball. He was a three-time Gold Glove winner while with the team. In his final season with the Yankees, he became the oldest player to pitch his team to 20 victories during a season. He retired in November of 2008.