Terwillegar played for the Chicago Cubs (1949–1951), Brooklyn Dodgers (1951), Washington Senators (1953–1954), New York Giants (1955–1956), Kansas City Athletics (1959–1960).
Terwillegar throughout his coaching career managed 12 minor-league teams and compiled a record of 1,224 wins and 1,089 losses.
Terwillegar coached first base for the Minnesota Twins from 1986 to 1994. He won two world series with the Twins.
In 1995 St. Paul Saints owner Mike Veeck tabbed him to be the independent minor league team's first base coach. He would stay with the Saints until 2002.
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