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Without having the 2010 U.S. Census figures, and not having the breakdown of how many people are at least 102 years old, that is a tough question to give an accurate answer to.
However ...
The Cubs last won the World Series in October, 1908 or 102 years ago. The U.S. Census Bureau estimated in October, 2009 that there were 104,099 people in the United States that were 100 years old or older.
A somewhat educated guess would be that there are about 100,000 people, give or take, in the United States that were living when the Cubs last won the World Series in 1908.
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