Craig Sager grew up in Illinois and has been rooting for the Cubs his whole life. This season he threw out a first pitch at Wrigley Field and led the crowd in “Take Me Out to the Ballgame.”

And it turns out the TNT sideline reporter puts his money where his mouth is.

According to Sager’s son, Craig Jr., Sager has bet on the Cubs to win the World Series every single year since 1981, as described in his not-yet-released autobiography “Living Out Loud.” This week, he cashed in on a $1,000 bet, as his team won its first World Series title since 1908.

In December, the Cubs were going off at about 6/1 to win the World Series, meaning Sager is likely due for a check of something like $6,000. Not bad, not bad.

In even better news for Sager and his family, he apparently had a successful procedure this week as he continues to fight leukemia. Sager has been pretty much bed-ridden in recent months, but he did get an allowance from his doctor to go to an NLCS game at Wrigley Field.

The Cubs’ World Series title has produced so many great stories about people who have waited incredibly long times to see their favorite team win a championship, and Sager’s is as touching as any. As he wrote in his book to explain why he kept picking the Cubs, “You gotta think positive.”

About Alex Putterman

Alex is a writer and editor for The Comeback and Awful Announcing. He has written for The Atlantic, VICE Sports,, and more. He is a proud alum of Northwestern University and The Daily Northwestern. You can find him on Twitter @AlexPutterman.

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