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Probably most of Joe Dimaggio's career, for starters. The Phillies were historically bad, the Browns sucked, the As had fallen apart after Connie sold everyone, the Senators, the Casey Stengel Braves…lots of options. (The White Sox were largely mediocre and the Cubs ran out of gas in the late 1940s, too.)
Pretty sure that most of the winningest teams accomplished the feat. Let's check 1909, for example.
Not only did the World Champion Pirates (110 wins) outpace the combined efforts of the Braves (45 wins) and Cardinals (54 wins), but you could leave the Braves (or whatever they were that season) out of it, and combine the 6th place Dodgers (55 wins) with the 54 for St. Loo and it still doesn't add up to 110.
And that's just one 8-team league. There are probably dozens of cases.
Also the 2nd-place Cubs had 104 wins so they were better than Boston and either Brooklyn or StL and yet they didn't come within 5 games of the pennant.
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