Upshaw was drafted by the Blue Jays from the Yankee organization in 1977. After a couple of seasons in the minors and as a part-time first baseman and outfielder, Upshaw took over as the regular Blue Jay first baseman from John Mayberry, who had been the franchise’s premier power hitter. In 1982 (his first season as regular first baseman), Upshaw set a team record for extra-base hits. He broke the record the following year, hitting .306 with 27 HR, 99 runs scored, and a team-record 104 RBI. He had at least one RBI in a team-record eight straight games in September 1983.
Although he remained a good defensive first baseman, Upshaw’s offensive production declined over the next several seasons. The Blue Jays were deterred from getting rid of him by his penchant for hitting well in spring training and the early season, and because Upshaw was highly respected and popular. But the emergence of Fred McGriff led to Upshaw’s 1988 trade to the Indians, where he was disappointing as their full-time first baseman. After the season, he went to Japan to finish his career. Upshaw’s cousins Gene and Marvin played in the National Football League, with Gene becoming the director of the NFL Players’ Association.