In 1995, the A's traded Sierra to the New York Yankees for Danny Tartabull. After helping the Yankees reach the playoffs for the first time in 14 years in 1995, Sierra was traded to the Detroit Tigers with Matt Drews for Cecil Fielder. Sierra was considered a journeyman because of playing for numerous teams during the late-1990s, including the Reds, Blue Jays, White Sox and Indians. After making a comeback with the Rangers in late 2000, he would go on to achieve moderate success with the Rangers in 2001, winning AL Comeback Player of the Year, and Mariners in 2002. In 2003, during Sierra's third stint with the Rangers, he was traded back to the Yankees, who were looking for a power-hitter off the bench. Sierra was an important part of the 2004 Yankees, a team that hit over 240 home runs. Sierra himself slugged 17 of those homers as the usual designated hitter, playing in 56 games at the position.