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Would Lester have had a better chance winning another World Series ring in 2015 if he signed with Boston, Los Angeles or San Francisco? No question, but it wouldn’t have come close to the satisfaction of winning a title on the north side of Chicago, a feat that hasn’t happened in more than a century.

“107 years,” said Cubs president Theo Epstein.

Lester is aware of what he signed up for. He was working his way through the Red Sox system in 2004 when the team made history, winning their first World Series title in 86 years. Make no mistake, Lester knows what it feels like to win a championship. He was a member of the 2007 and 2013 Red Sox teams. But this — bringing a World Series title to Chicago — will cement his legacy. You can’t buy that experience.

He envies the ’04 Red Sox. Guys like Kevin Millar, Dave Roberts and Gabe Kapler. Lester relishes the opportunity to replicate the experience some 1,000 miles from Boston.

“To be a part of something like that would truly be special and unbelievable,” Lester said in his introductory press conference. “Those guys (’04 Red Sox) will live as legends forever. This takes nothing away from Dave Roberts, but he stole one base. And he’s a legend. To see what it did to the organization, how it changed the perception. That was one of the reasons that led us here.”

Now the heavy lifting starts.

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About the author

John Strubel

Hi. My name is John Strubel. Thanks for visiting my website. I write primarily about my passion: baseball. In addition, I occasionally publish posts and podcasts related to sports media, journalism and technology impacting the industry. You can also connect with me on social media @johnstrubel.

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