Note: I am only counting Pennants won by teams still in existence. So the 19th Century Pennants won by the team now known as the Chicago Cubs count. Those won by the Boston team that became the Milwaukee, then Atlanta Braves, will be in italics and not ranked.
All ties in this ranking are broken by most recent finish.
1. New York Yankees, 40: 1921, '22, '23, '26, '27, '28, '32, '36, '37, '38, '39, '41, '42, '43, '47, '49, '50, '51, '52, '53, '55, '56, '57, '58, '60, '61, '62, '63, '64, 76, '77, '78, '81, '96, '98, '99, 2000, '01, '03, '09.
New York National League teams combined -- Giants, Dodgers & Mets, 34: 1888, '89, '89, '90, '99, 1900, '04, '05, '11, '12, '13, '16, '17, '20, '21, '22, '23, '24, '33, '36, '37, '41, '47, '49, '51, '52, '53, '54, '55, '56, '69, '73, '86, 2000. So, yeah, even combined, they can't top the Yankees.
Dodgers combined, 26: 1889, '90, '99, 1900, '16, '20, '41, '47, '49, '52, '53, '55, '56, '59, '63, '65, '66, '74, '77, '78, '81, '88.
Giants combined, 22: 1888, '89, 1904, '05, '11, '12, '13, '17, '21, '22, '23, '24, '33, '36, '37, '51, '54, '62, '89, 2002, '10, '12.
2. St. Louis Cardinals, 21: 1885, '86, '87, '88 (American Association, thereafter National League), 1926, '28, '30, '31, '34, '42, '43, '44, '46, '64, '82, '85, '87, 2004, '06, '11, '13.
Braves combined, 21: 1872, '73, '74, '75, '77, '78, '83, '91, '92, '93, '97, '98, 1914, '48, '57, '58, '91, '92, '95, '96, '99.
New York Giants, 17: 1888, '89, 1904, '05, '11, '12, '13, '17, '21, '22, '23, '24, '33, '36, '37, '51, '54.
3. Chicago Cubs, 16: 1876, '80, '81, '82, '85, '86, 1906, '07, '08, '10, '18, '29, '32, '35, '38, '45.
A's combined, 15: 1902, '05, '10, '11, '13, '14, '29, '30, '31, '72, '73, '74, '88, '89, '90.
Boston Braves, 14: 1872, '73, '74, '75 (National Association, thereafter National League), '77, '78, '83, '91, '92, '93, '97, '98, 1914, '48.
4. Boston Red Sox, 13: 1903, '04, '12, '15, '16, '18, '46, '67, '75, '86, 2004, '07, '13.
Brooklyn Dodgers, 13: 1889 (American Association, thereafter in National League), '90, '99, 1900, '16, '20, '41, '47, '49, '52, '53, '55, '56.
5. Detroit Tigers, 12: 1907, '08, '09, '34, '35, '40, '45, '68, '84, '87, 2006, '12.
6. Cincinnati Reds, 10: 1882 (American Association, thereafter National League), 1919, '39, '40, '61, '70, '72, '75, '76, '90.
7. Los Angeles Dodgers, 9: 1959, '63, '65, '66, '74, '77, '78, '81, '88.
8. Pittsburgh Pirates, 9: 1901, '02, '03, '09, '25, '27, '60, '71, '79.
Philadelphia Athletics, 9: 1902, '05, '10, '11, '13, '14, '29, '30, '31.
9. Philadelphia Phillies, 7: 1915, '50, '80, '83, '93, 2008, '09.
Browns/Orioles combined, 7: 1944, '66, '69, '70, '71, '79, '83.
10. Oakland Athletics, 6: 1972, '73, '74, '88, '89, '90.
11. Baltimore Orioles, 6: 1966, '69, '70, '71, '79, '83.
12. Chicago White Sox, 6: 1901, '06, '17, '19, '59, 2005.
Senators/Twins combined, 6: 1924, '25, '33, '65, '87, '91.
13. San Francisco Giants, 5: 1962, '89, 2002, '10, '12.
14. Atlanta Braves, 5: 1991, '92, '95, '96, '99.
15. Cleveland Indians, 5: 1920, '48, '54, '95, '97.
16. New York Mets, 4: 1969, '73, '86, 2000.
17. Minnesota Twins, 3: 1965, '87, '91.
Washington Senators, 3: 1924, '25, '33.
18. Texas Rangers, 2: 2010, '11.
19. Miami Marlins, 2: 1997, 2003.
20. San Diego Padres, 2: 1984, '98.
21. Toronto Blue Jays, 2: 1992, '93.
22. Kansas City Royals, 2: 1980, '85.
23. Tampa Bay Rays, 1: 2008.
24. Colorado Rockies, 1: 2007.
25. Houston Astros, 1: 2005.
26. Los Angeles Angels of Anaheim, 1: 2002.
27. Arizona Diamondbacks, 1: 2001.
28. Milwaukee Brewers, 1: 1982.
Milwaukee Braves, 2: 1957, '58.
St. Louis Browns, 1: 1944.
29. Washington Nationals, none in 9 seasons.
30. Seattle Mariners, none in 36 seasons.
Montreal Expos, none.
Kansas City Athletics, none.
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