Cubs starting pitcher Jon Lester joined “Off The Mound with Ryan Dempster” to head down memory lane. They went back to 2014 when Lester signed a 6-year contract with the Cubs worth $155 million. The main reason Lester was brought to the Cubs was to win a title.

“I don’t think you ever fully live up to the amount of money that we make…I don’t think that contract would have been justified if we don’t win,” Lester said.

The 108-year title drought was broken just two years later in 2016 when the Cubs took home their first World Series title after a 7 game battle against the Cleveland Indians. 

“We accomplished what I came here to do. It’s hard to describe the emotions fully that really went into that,” Lester said.

Lester then went into detail about the difference between starting a game, especially in the World Series, and sitting in the bullpen, like he was in Game 7.

“To be down there and actually wait for that phone to ring, sitting around. When it rings, it’s like ‘Hey, you need to get going.’ It’s a feeling that I don’t like to be honest. I give all respect to what relievers do day in and day out when that phone rings.”