Although he was born in Lakewood, Ohio (USA), Shepard lived with his family after the age of 14 in Montréal, Québec (Canada),[1] where he attended McGill University.

In 1952 and part of 1953, Shepard took a break from managing, becoming strictly a relief pitcher for the Hollywood Stars of the Pacific Coast League.

He resumed his managerial career in the middle of the 1953 season in the Pittsburgh system, winning the 1956 and 1957 Western League championships with the Lincoln Chiefs.

From 1958 through 1966, he managed at the Triple-A level for Pittsburgh with the Salt Lake City Bees and Columbus Jets, notching three first-place finishes.

In his two seasons as skipper of the Bucs, Pittsburgh finished sixth in the ten-team National League in 1968 (with a record of 80–82) and fourth in the NL East at 84–73 in 1969 (when Shepard was released, that September 25).