How Close Have the Cubs come to Winning the World Series?

I don’t know if you’ve heard, but the Cubs are in the World Series. But what you probably don’t know is that they haven’t won it since 1908. OK, we’re all well aware and will be reminded of it a thousand times over the next week and a half. We’ll see highlights of the ball rolling through Leon Durham’s legs, a fan trying to catch a foul ball, Alex Gonzalez botch a potential double play ball, images of a black cats and goats, and a lot of photos of Tinker, Evers & Chance.

So if you’ll indulge me, let’s see how close the Cubs have come to winning the World Series in each season since 1903. For teams that reached the postseason, I’ll use their highest series win probability in their final series. For teams that failed to advance to the playoffs, I’ll use the highest pennant win probability they reached during the regular season.

Cubs Highest Championship Probability by Sesaon *Click on image to expand

If you’re familiar with Chicago Cubs history, you know they were very good during the late 1920s and 1930’s. In fact, they had the second highest winning percentage of any team from 1929-1939. They just happened to run into Connie Mack’s A’s, Ruth and Gehrig’s Yankees, Greenberg and Cochrane’s Tigers, and Gehrig and DiMaggio’s Yankees.

They also came out on top of the National League in both seasons that were most affected by World Wars, 1918 and 1945. These were seasons that saw rosters severely impacted with some of the games best players going into the service or defense industry. The following seasons, when players returned to their teams, the Cubs fell to 21 games behind in 1919 and 14 1/2 games in 1946.

Then, from 1946 until 1983, the Cubs came no closer to winning the World Series than a 23.5% chance. The high point was 1969, when on August 13th, they were up 9 games in the National League East and had a 94.2% probability of winning the division. As we all know, the Amazin’ Mets came from behind to win the division and the World Series. But even if the Cubs had won the division, they would have still had to go through Hank Aaron’s Braves and the 109 win Orioles.

The Cubs have made the postseason six times since 1984, advancing to the NLCS on three different occasions. And just like the Cubs would have had to get past the Tigers (1984), A’s (1989) and Yankees (2003), this years Cubs will have to get past the Indians. The only difference is that the 2016 team will actually get a chance to do it.

Finally, if you prefer the data in a table, here is the year-by-year data, sorted by highest World Series win probability.

Year Probability Postseason
1945 77.4% World Series
1935 67.4% World Series
1932 57.8% World Series
1929 54.8% World Series
1938 53.4% World Series
1918 52.2% World Series
1910 50.9% World Series
2016 50.0%
2003 48.9%
1984 45.6% NLCS
1937 43.0%
1927 41.0%
1930 40.1%
1936 33.4%
1989 29.3% NLCS
1911 26.4%
2015 26.4% NLCS
1969 23.5%
1915 21.7%
1967 20.2%
1917 20.2%
1977 19.3%
1973 19.3%
1934 18.5%
1947 16.5%
1924 16.3%
1909 15.9%
1933 15.6%
2008 15.1% NLDS
1928 13.4%
1970 13.3%
1913 13.2%
2007 13.0% NLDS
1985 12.7%
1998 12.5% NLDS
1978 12.4%
1920 12.4%
1926 12.3%
1914 12.0%
1922 11.6%
1958 10.9%
1952 10.8%
1912 10.7%
2001 10.6%
1975 10.6%
1923 10.5%
1931 10.3%
1939 10.0%
1955 9.8%
2004 9.8%
1963 9.7%
1916 9.7%
1987 9.4%
1925 9.4%
1951 9.2%
1946 9.1%
1919 9.1%
1921 8.9%
1950 8.8%
1953 8.4%
1941 7.9%
1959 7.8%
1940 7.3%
1980 7.3%
1995 7.2%
1949 7.2%
1965 7.2%
1954 7.1%
1948 7.1%
1942 7.0%
1961 7.0%
1960 7.0%
1956 6.8%
1944 6.7%
1943 6.6%
1988 6.5%
1991 6.5%
1972 6.3%
1968 6.2%
1979 6.1%
1957 5.9%
1990 5.9%
2009 5.8%
1964 5.8%
1976 5.7%
1999 5.2%
1981 5.2%
1974 5.1%
1962 5.0%
1966 4.9%
1982 4.7%
1992 4.7%
1971 4.6%
1996 4.5%
1986 4.4%
1983 4.2%
2005 4.1%
2006 4.0%
2013 3.8%
1993 3.6%
1994 3.5%
1997 3.4%
2014 3.4%
2000 3.3%
2011 3.2%
2010 3.2%
2002 3.0%
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