Upshaw was drafted by the New York Yankees in the 5th round of the 1975 Major League Baseball draft.
He was selected by the Toronto Blue Jays in the Rule 5 draft on December 5, 1977,[2] and in 1982, became the Blue Jays' regular first-baseman, leading the team in home runs with 21, RBI with 75, and extra base hits.
In 1983, Upshaw became the first Blue Jays player to reach the 100 RBI plateau in a season, driving in 104 runs while batting .306.[3]
Prior to the 1988 season, Upshaw's contract was purchased by the Cleveland Indians.[4] At the time of his retirement, he was Major League Baseball's career leader in home runs (123) and RBIs (528) for players whose surname begins with the letter U.[citation needed]
During 2006 and 2007, Upshaw served as the first base coach for the San Francisco Giants. When Barry Bonds broke Hank Aaron's career home run record, Upshaw was the first to congratulate him with a high-five as Bonds circled the bases.
He is the cousin of the late NFL Hall of Fame guard Gene Upshaw and former NFL defensive lineman Marvin Upshaw.
In May 2007 Upshaw's son Chad signed a three-year contract with the Carolina Panthers as a Tight End after going undrafted following his graduation from Buffalo.
Upshaw, who resides in Fairfield, Connecticut, spent eight seasons as manager of the independent Bridgeport Bluefish over two stints (1998-2000, 2010-2014) and also managed the club during the second half of their 2009 season following the resignation of manager Tommy John.
Upshaw was a combined 571-543 (.513) during the regular season, leading the Bluefish to four of their playoff appearances (1998-2000, 2010), three trips to the Atlantic League Championship Series (1998-1999, 2010) and their lone league championship (1999) and was named league Manager of the Year in 1998 and 2010.
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