With a winning season being defined as playing over .500 Baseball (more wins than losses) The New York Yankees had 88 winning seasons out of 109 total seasons from 1901 when the franchise began as the Baltimore Orioles.
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Since 1969 when Major League Baseball started the playoff format, the New York Yankees have made the playoffs 22 times. 18 Eastern division titles, and 4 wild card berths.
Let's see here...there are 30 teams in the MLB. Each team has one owner, except for the Oakland Athletics, who have two. 30+1=31, so there are 31 owners in all of Major League Baseball.