The son of MLB second baseman Sandy Alomar Sr., Alomar followed in his father's footsteps, signing with the Padres as an amateur free agent in 1985. He made his major league debut with the team three years later, establishing himself as an exceptional base-stealing, hitting, and fielding threat before becoming an All-Star in 1990. He was traded to the Blue Jays the following off-season, leading the team to three consecutive American League Championship Series (ALCS) appearances and being named the 1992 ALCS Most Valuable Player (MVP), culminating in back-to-back World Series championships in 1992 and 1993. Alomar signed with the Orioles after the 1995 season, led the team to two ALCS appearances, and won the 1998 All-Star Game MVP Award in his final year with the team. He then joined the Indians for three seasons and had the most productive years of his career in 1999 and 2001, again leading his team to the playoffs and becoming an AL MVP Award finalist both years. Alomar spent the final years of his career with the Mets, White Sox, and Diamondbacks before retiring at spring training in 2005.