The “most winningest” team in baseball

Rob Boudreau
August 13, 2009

With 26 World Series championships, the New York Yankees are by far the most successful franchise in professional sports, and certainly the “most winningest” in baseball. With a 24.07 Championship Winning Percentage, the Yankees have proven themselves time and time again. If you name some of the greatest players in history, there’s a good chance they wore the Yankee pinstripes. Yogi Berra, Joe DiMaggio, Whitey Ford, Reggie Jackson, Mickey Mantle, Babe Ruth. The list goes on and on.

The history of success for the New York Yankees is incredible. They have a number of accomplishments exclusive to their history, including being the only franchise since 1920 to win at least one World Series in every decade except the ’80s. They won five in a row from ’49-’53 under manager Casey Stengel. The next closest to that is four in row, which has also only been done once – by the ’36-’39 New York Yankees. The 1998-2000 teams are the only to three-peat since the ’72-’74 Athletics, who were followed two years later by a pair of Yankees victories. Is the success starting to make you dizzy? Let’s move on.

The only other baseball team with a double digit total for World Series’ is the St. Louis Cardinals. With 10 wins in 117 years, they have a 8.55 CWP. Despite their age, it wasn’t until 1926 before the team won their first, winning sporadically in the ’30s, ’40s and ’60s. They almost seem like a model franchise. They weren’t losing too often to create restless fans, like oh, say, the Cubs, but they weren’t winning too often to piss off the rest of the country, like a certain pinstriped team. In the last 42 years, only five World Series have featured two teams that have remained in their original cities since the formation of the American League in 1901. St. Louis has been part of four of those and won two of them.

In 1960, Bill Mazeroski made baseball history. Leading off the bottom of the ninth of Game 7, Mazeroski took a 1-0 pitch from New York’s Ralph Terry over the left field wall to break a 9-9 tie. It was the first time a World Series was ended by a home run; the only other time being Joe Carter for the Toronto Blue Jays in 1993. For the Pirates, it was their third of five World Series wins (4.10 CWP), but it was easily the greatest. Their last World Series was in 1979. The Pirates haven’t been to the playoffs since.

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Those Blue Jays are quite obviously the “most winningest” Canadian franchise. Being one of two – the other being the Montreal Expos, who never went to the World Series – the Blue Jays’ back to back wins in ’92 and ’93 give them a 6.25 CWP. With some of the greatest players of the era like Hall of Famers Dave Winfield, Paul Molitor and Ricky Henderson, it didn’t even matter that almost half the roster was changed in between seasons. Ask any Canadian and they’ll certainly tell you where they were when Carter hit his World Series-winning home run in 1993. It was one of the only non-hockey related sports moments that unified the cold country to the north.

The Florida Marlins and Arizona Diamondbacks are two anomalies when it comes to the “most winningest” in sports. They are the only two on any of the four major sports’ top five who have less than 37 years experience. The Marlins have been around since 1993 and they won the World Series in ’97 and ’03 (12.50 CWP), while the Diamondbacks came into baseball in ’98, winning in ’01 (9.09 CWP). While the teams were great in their own rights, these two franchises are the exact reason why significant sample sizes are needed in scientific studies.

If the Yankees manage to continue their hot run in 2009 and make it through October with a World Series, their CWP will go from 24.07 to 24.77. If Florida prevails – which is not out of the realm of possibility – their CWP will shoot up from 12.50 to 17.65. If they repeat in 2010, it would be at 22.22. This is absolutely unfair to the teams with at least some semblance of history. There are 15 franchises who are not the New York Yankees that have existed for over 100 years, all of whom have a lower CWP than the Marlins and Diamondbacks. Take that into consideration when you place these two at second and third on the overall list.

When you make a baseball “most winningest” list, it’s not improper to break it down into eras. While that is another story altogether, it is kind of fun to say that the Chicago Cubs are the most winningest team from 1907-1908.

Overall, however, the Cubs are the recipients of the biggest slap in the face in professional sports. They haven’t won a World Series since 1908, over 100 years now. In that year, they actually managed to repeat as champions, giving the North Siders their only two wins in franchise history (1.50 CWP). They are the proud owners of the lowest CWP in sports among teams who have at least one championship.

So that’s it, the “most winningest” broken down sport by sport for your pleasure. As you’ve seen, each sport is unique in its list of champions for many reasons, and each sport has its own subtle stories behind the stories, any one of which being worthy of its own 15 minutes of fame. Go ahead and look back at the stats and see if you can find your own fun facts worth mentioning and leave some comments. The stories certainly don’t end here!

The table below is accurate as of Nov. 1, 2010. The article itself is only accurate of its publication date. -TheGP

Team EST. Years Wins CWP
New York Yankees 1901 110 27 24.55
Florida Marlins 1993 18 2 11.11
Arizona Diamondbacks 1998 13 1 7.69
St. Louis Cardinals 1892 119 10 8.40
Oakland Athletics 1901 110 9 8.18
Boston Red Sox 1901 110 7 6.36
Toronto Blue Jays 1977 34 2 5.88
Los Angeles Dodgers 1890 121 6 4.96
San Francisco Giants 1883 128 6 4.69
New York Mets 1962 49 2 4.08
Pittsburgh Pirates 1887 124 5 4.03
Cincinnati Reds 1882 129 5 3.88
Detroit Tigers 1894 117 4 3.42
Baltimore Orioles 1901 110 3 2.73
Minnesota Twins 1901 110 3 2.73
Chicago White Sox 1900 111 3 2.70
Kansas City Royals 1969 42 1 2.38
Atlanta Braves 1871 140 3 2.14
Los Angeles Angels 1961 50 1 2.00
Cleveland Indians 1901 110 2 1.82
Philadelphia Phillies 1883 128 2 1.56
Chicago Cubs 1876 135 2 1.48
Colorado Rockies 1993 18 0 0.00
Houston Astros 1962 49 0 0.00
Milwaukee Brewers 1969 42 0 0.00
San Diego Padres 1969 42 0 0.00
Seattle Mariners 1977 34 0 0.00
Tampa Bay Rays 1998 13 0 0.00
Texas Rangers 1961 50 0 0.00
Washington Nationals 1969 42 0 0.00


(July 23) – The “most winningest” team in hockey

(July 30) – The “most winningest” team in football

(August 6) – The “most winningest” team in basketball

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The Author:

Rob Boudreau