He played for the Brooklyn Dodgers in 1935 and for the Philadelphia Athletics in 1943, and served as acting manager of the Detroit Tigers for the latter half of the 1966 season after his two immediate predecessors in the post were stricken with terminal illnesses.

A CCBL all-league selection as an outfielder, it was reported that Skaff "covers acres of territory, catches everything in sight," and was "the dread of all opposing pitchers".

Skaff's major league debut came on September 11 in the Dodgers' 7–4 loss to the Cincinnati Reds at Crosley Field, when he entered the game in the ninth inning to pinch-hit against Paul Derringer, and grounded out.

His lone major league home run came on September 27 in the second game of a doubleheader against the St. Louis Browns, a grand slam off Al Hollingsworth that reportedly hit the roof at Shibe Park.

After 57 games as the Tigers' manager, Swift was hospitalized during the July 11–13 All-Star break for what appeared to be a stomach ailment; however, his malady proved to be lung cancer and he was forced to immediately give up the reins.

Skaff, who had begun 1966 as Detroit's bench coach, then moved to third base under Swift, became the team's second acting manager of the season on July 14 and finished the campaign.

[7] He never managed again in the majors (his 40–39 career record produced a winning percentage of .506), but returned to Detroit as a coach under Billy Martin in 1971.