Memories of the 2011 Red Sox keep Theo Epstein from looking too far ahead with the 2016 Cubs

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Cubs president Theo Epstein speaks to the media at Wrigley Field on August 29th.

CHICAGO – The moment that brought him to the place where he currently sits is one that the Cubs’ president would like to remember and forget all at the same time.

But when your team leads their division by 14 games just a few days from September, Theo Epstein thought Monday was the best time to use a painful moment to give a lesson on looking to far ahead with his front-running Cubs.

“Once you go through a year when you have a double-digit lead right before Labor Day and screw it up and you don’t even get to October you don’t take anything for granted,” said Epstein – who remembers a big lead lost five years ago that ended an era of his career.

As General Manager of the Red Sox, Epstein watched his team take a nine-game lead in the Wild Card on September 3rd only to finish the final month with a 7-20 record. In an odd twist of fate, it was Joe Maddon’s Tampa Bay team that pulled off an extra inning win on the final day of the season minutes after a loss by the Red Sox to send Epstein’s team home early.

That team became the first in Major League Baseball history to have a nine-game lead in September and failed to make the playoffs.

"Never take anything for granted," said Epstein when remembering the September collapse. "We're still trying to win each game and trying to win each series. You have to have a broad perspective and understand what might lie ahead but you have to go earn it and that has been our team's approach from the very beginning is not to accept some of the praise that's come our way but go out and try to earn it through our play.

"That's definitely true in the month of September."

Oddly enough it was that collapse that led Epstein to a new opportunity with the Cubs and he would eventually hire Maddon, who in a way ended his successful run in Boston with a late-season run five years ago. While some view that as fate for the pair to come together to end the Cubs' 108-year World Series championship drought, Epstein would rather it be a lesson in overconfidence.

"I guess that's the only good thing to come out of September of 2011," said Epstein. "I'll never look too far ahead."

To the point where he's willing to look back at a painful memory to prevent it.