Before 69

[Panzram]

Before expansion in 1969, the AL Champion with the worst ever record was a team that featured the last Triple Crown winner to date. Who was it?

Yankees, 1949
Red Sox, 1967
Red Sox, 1941
Tigers, 1908

[Toy Cannon]

Boston/'67

[Panzram]

Red Sox, 1967. Right. I apologize for the stupid trivia. Just realized how bad they were.