Even after dropping six of their last ten, the Chicago Cubs are still well on pace to notch over 100 wins this season.  This is exciting news for the Cubs organization and fans, but the ultimate question still remains:  Can they win the World Series?

As shocking as it seems, breaking 100 wins is not a good sign for World Series dreams.  I was interested in baseballs winningest teams when ESPN mentioned the Cubs were off to the fastest 30 game start since 1984.  I decided to focus on more recent teams under the current playoff format since some of the teams winning over 100 only had to win one series (or none) to make the World Series.  The results were shocking.  (See table at the end of the article)

Since 1995,  22 teams have posted 100+ win seasons.  Of those 22, only six even made the World Series.  Going one step further, only two won.  Both were the New York Yankees in 1998 and 2009 (Go Yanks!).  That’s about a 27.3% success rate for teams winning 100+ games to get to the World Series and a mere 9.1% success rate for winning the World Series.

Even more bizarre, in years when multiple teams posted 100+ win season, none went on to win the World Series.  This stat could be an interesting one to keep tabs on come October if the Orioles and Nationals (also currently on pace for right around 100 wins) keep at their pace.  If adjusting for the years where multiple teams won 100+ games and counting them as one (since only one could win the World Series), the numbers increase a bit:  42.9% went on to make the World Series and 14.3% went on to win.

All numbers aside though, it’s impossible to deny how good these Cubs are this year.  I personally hope they do win well over 100 games and go on to win the World Series, even though it seems the numbers are against them.  Not to mention how crazy it would be for them to finally end the 107 year World Series drought.

Teams with 100+ wins in current playoff format and their playoff finish

2001 Seattle Mariners AL 116 46 0.71605 Lost ALCS
1998 New York Yankees AL 114 48 0.70370 Won World Series
1995 Cleveland Indians AL 100 44 0.69444 Lost World Series
1998 Atlanta Braves NL 106 56 0.65432 Lost NLCS
2004 St. Louis Cardinals NL 105 57 0.64815 Lost World Series
2002 New York Yankees AL 103 58 0.63975 Lost ALDS
2009 New York Yankees AL 103 59 0.63580 Won World Series
1999 Atlanta Braves NL 103 59 0.63580 Lost World Series
2002 Oakland Athletics AL 103 59 0.63580 Lost ALDS
2002 Atlanta Braves NL 101 59 0.63125 Lost NLDS
2011 Philadelphia Phillies NL 102 60 0.62963 Lost NLDS
2001 Oakland Athletics AL 102 60 0.62963 Lost ALDS
1998 Houston Astros NL 102 60 0.62963 Lost NLDS
1997 Atlanta Braves NL 101 61 0.62346 Lost NLCS
2004 New York Yankees AL 101 61 0.62346 Lost ALCS
2003 New York Yankees AL 101 61 0.62346 Lost World Series
2003 Atlanta Braves NL 101 61 0.62346 Lost NLDS
2003 San Francisco Giants NL 100 61 0.62112 Lost NLDS
2005 St. Louis Cardinals NL 100 62 0.61728 Lost NLCS
2015 St. Louis Cardinals NL 100 62 0.61728 Lost NLDS
2008 Los Angeles Angels AL 100 62 0.61728 Lost ALDS
1999 Arizona Diamondbacks NL 100 62 0.61728 Lost NLDS