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Chicago Cubs: Should Joe Maddon be optimistic about an extension?

Last offseason, the decision to not offer Joe Maddon a contract extension was one of many storylines that dominated Chicago Cubs circles. That call placed a lame-duck label on the 65-year-old two-time Manager of the Year and raised more than a handful of questions regarding his future.

Prior to the Cubs series finale on Sunday, Maddon spoke on the likelihood he remains at the helm past the next two months, saying the optimism is ‘very, very high’ he’s on the North Side for ‘a couple more years, at least.’

Entering Monday, Chicago holds a slim two-game edge over the St.