Molitor was born in Saint Paul, Minnesota. After graduating from Cretin High School, he was selected in the 28th round of the 1974 free agent draft as a pitcher by the St. Louis Cardinals, but opted instead to attend college at the University of Minnesota. He was a three-year starter for the Golden Gophers, earning All American honors as a shortstop for his sophomore and junior years. Between his junior and senior seasons, Molitor suffered a broken jaw.

Although Molitor wanted to remain with Milwaukee when he became a free agent after the 1992 season, the franchise offered him a one-year contract with a $900,000 pay cut (to $2.5 million), while the Toronto Blue Jays offered a three-year, $13 million ($22,000,000 in current dollar terms) deal, leading to his signing with the Blue Jays. Agent Ron Simon said, "I was also talking with Milwaukee, but it became clear to us that Milwaukee didn't have the same kind of interest in signing Molitor, perhaps because of their financial situation."  Molitor quickly became an offensive juggernaut. In 1993, Molitor led the AL in plate appearances (725) and hits (211) and hit .332 with 22 home runs and 111 RBI. Returning to the playoffs for the first time since 1982, he was a key part of the Blue Jays' second World Championship. Molitor hit 2 doubles, 2 triples, and 2 home runs in the Series, earning the World Series MVP Award and tied a World Series record by batting .500 (12-for-24) in the six-game series. In addition, after DHing all season, Molitor played two games at first base and one at third base in the three Series games in Philadelphia.  In 1994, a strike-shortened season, Molitor hit .341 and led the AL in games played (115) and singles (107). He also stole 20 bases that season without ever being caught, one short of Kevin McReynolds' 1988 major league record of 21. Molitor's average dropped to .270 in 1995, his lowest mark in more than ten years.

What positions did he play for the Toronto Blue Jays?
Molitor played two games at first base and one at third base in the three Series games in Philadelphia.