Ashford attended Covington High School in Covington, Tennessee, and was the starting quarterback of the football team his senior year. After a short stint at the University of Mississippi, Ashford transferred to Southwest Tennessee Community College. He played American Legion ball for Post 1 in Memphis, and was the George W. Rulon Player of the Year in 1973.
Upon being drafted by the Padres in the 1974 January Draft, Ashford was assigned to the Walla Walla Padres of the Northwest League. Playing primarily shortstop, Ashford batted .243 with four home runs & thirty runs batted in. His transition to third base began the following season with the Texas League's Alexandria Aces. His twelve home runs & 67 RBIs for the Amarillo Gold Sox in 1976 earned him a September call up to the Padres. He went 3-for-5 with a walk, a double & two stolen bases in six plate appearances.
Ashford began the 1977 season in triple A. On June 8, the Padres sold Doug Rader's contract to the Toronto Blue Jays. A week later, Bobby Valentine, his replacement at third base, was traded to the New York Mets. The Padres experimented with Gene Tenace & Dave Kingman (acquired for Valentine) at third before calling Ashford back up at the beginning of July. He collected his first major league RBI in his second start. On July 5, he hit his first major league home run off the Houston Astros' Bo McLaughlin with two outs in the ninth inning to send the game to extra innings. In the twelfth, he singled in the winning run. He won the starting job at third for the remainder of the season, and batted .217 with three home runs & 24 RBIs.

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