Born William Herman Schaefer in the South Side of Chicago, to German immigrant parents, he played in two World Series with the Tigers.

One of his most famous exploits was stealing first base, which was perhaps recalled in Lawrence Ritter's The Glory of Their Times by Detroit outfielder Davy Jones.

On August 4, 1911, Schaefer tried the same stunt again, this time for the Washington Senators, inspiring the Chicago White Sox' manager, Hugh Duffy, to come out of the dugout to protest.

The others in the meeting, discussing ground rules, players' pool, etc., were "Garry" Herrman, owner of the Cincinnati Reds and head of the Commission; the league presidents Ban Johnson and Harry Pulliam, the managers Hughie Jennings and Frank Chance, and the two umpires, Hank O'Day and Jack Sheridan.

It was supposedly a trivial question, but Schaefer made a point: If there is a tie game in the Series, do the players share in its gate receipts?

After a short discussion with Johnson and Pulliam, Herrman answered, 'The players' pool will include receipts from any tie games.'

Schaefer was a pioneer of baseball clowning, and his vaudeville act with teammate Charley O'Leary was inspiration for the MGM musical Take Me Out To The Ball Game starring Gene Kelly and Frank Sinatra.

Schaefer once verbally "called" his shot before hitting a two-run home run on June 24, 1906 to put the Tigers up 3–2 against the Chicago White Sox in the top of the 9th.