As an infielder, Walewander's advancement to the majors was delayed by shortstop Alan Trammell and second baseman Lou Whitaker. "Wales" was finally summoned to Detroit on May 31, 1987, going 1 for 2 against the Minnesota Twins. Walewander primarily appeared as a defensive substitute or pinch-runner in the late innings. He was a key figure as the Tigers battled the Toronto Blue Jays for the division crown. In the 12th inning of the season's penultimate game against Toronto, pinch-hitter Walewander scooted home with the game-winning run after Trammell drilled a game-winning single through Toronto shortstop Manuel Lee's legs. Detroit won the division title the next day via a Frank Tanana 1–0 shutout. Walewander was not on the playoff roster, and Minnesota defeated Tigers in the ALCS.