Which MLB team has won the most pennants all time?

Answer 1

The New York Yankees have the most pennants in Major League Baseball history with 40.

They won (American League) pennants in: 1921, 1922, 1923, 1926, 1927, 1928, 1932, 1936, 1937, 1938, 1939, 1941, 1942, 1943, 1947, 1949, 1950, 1951, 1952, 1953, 1955, 1956, 1957, 1958, 1960, 1961, 1962, 1963, 1964, 1976, 1977, 1978, 1981, 1996, 1998, 1999, 2000, 2001, 2003 and 2009.

Of those years, they won the World Series 27 times, in: 1923, 1927, 1928, 1932, 1936, 1937, 1938, 1939, 1941, 1943, 1947, 1949, 1950, 1951, 1952, 1953, 1956, 1958, 1961, 1962, 1977, 1978, 1996, 1998, 1999, 2000 and 2009.