Two cities, one legend: Jon Lester reflects on one of a kind career with Sox, Cubs

Jul. 4—CHICAGO — Nobody's ever had a career like Jon Lester's.

There are plenty of guys who have won championships and become legends within their respective cities. Some enjoyed Hall of Fame careers, had their numbers retired and will never have to buy a drink in their respective towns again.

But to do it three times in two cities, for the Boston Red Sox and Chicago Cubs of all teams? And to beat cancer and help end a 108-year championship drought in the process?

Lester's experience truly was one of a kind.

This weekend the Red Sox and Cubs are facing off at Wrigley Field for a rare three-game series, and if anyone can appreciate what this matchup means, it's Lester. Having started his career in Boston before becoming arguably the greatest free agent signing in Chicago history, he carries a unique understanding of the two historic franchises, their legendary home ballparks and passionate fanbases.

"Any time you get historic franchises playing each other it's a pretty cool deal, I was spoiled to come up and play the Yankees with the Red Sox so many times," Lester said on Friday evening. "Any time you develop that much history it kind of adds to the whole game and the whole series."

This weekend The Eagle-Tribune caught up with Lester, who is now retired and enjoying family life after 16 seasons of Major League Baseball. Lester touched on his career, his time with the Red Sox and Cubs and life after baseball.

'You can't rank them'

One thing that stands out about Lester is just how many great moments he was a part of throughout his career.

As a 23-year-old youngster he picked up the series-clinching win in the 2007 World Series only months after beating cancer.

Six years later in 2013 he enjoyed one of the greatest postseasons by a starting pitcher in history, helping the Red Sox to another emotional title run in the wake of the Boston Marathon bombings.

Then three years later he delivered on the promise he made by signing with Chicago, helping the Cubs finally break their century-old curse and win the 2016 World Series. Any one of those accomplishments would be a crowning achievement for most players, yet for Lester, trying to compare the three titles is impossible because each came at such different times in his life and career.

"In '07 coming back from cancer and being part of that was a very unique and different experience for me and getting the opportunity to pitch, being a young guy, being around the older guys and seeing how it's done," Lester said. "And '13 being the guy that's relied upon in Game 1 and Game 5 and give good starts and give our team a chance to win and kind set the tone. Kind of being relied upon.

"And then signing with a team that hadn't won in 108 years and you're supposed to be the person that signs there to break that," he continued. "Different feelings in different circumstances and different responsibilities. I don't know if you can really rank them or put one ahead of the other just based on different points of my career and personal points of my career."

No hard feelings over turbulent Sox exit

For all the success Lester enjoyed in Boston, few would blame him if he harbored a grudge against the Red Sox for the way the club handled his exit. In the months after Lester played a starring role in the 2013 World Series title run, the Red Sox front office mishandled his contract negotiations and eventually traded him to the Oakland Athletics at the 2014 trade deadline.

While difficult at the time, Lester said that's not the case and he has nothing but love for the organization.

"I love the Red Sox. I think as you grow and you mature and you understand the game and understand the business of the game, you understand decisions have to be made whether they're hard or easy," Lester said. "You have to separate, and it's hard to do sometimes, but you have to separate your heart from your brain and understand that the game is a business and they have to do what's best for the organization.

"At the time it was tough, but like I said, as you get older you understand things and you understand that's part of what goes on," he continued. "I'll always love the Red Sox, they gave me the opportunity to be a big leaguer, not only be a big leaguer but be a pro and then a big leaguer, and then gave me an opportunity to pitch for a substantial amount of time and I was able to take it from there. Not only that but just how they treated my family and me when I went through all my stuff in '06 and '07. There were a lot of positives in there more so than just getting traded away."

Eventually Lester hopes to make it back to Boston, noting his kids weren't old enough to remember watching him pitch there. At some point he'll likely fly up with his family for a weekend getaway, though fans probably won't hear about it when they do.

"We've talked about taking them up and doing the whole Boston tour and going to see a game or two," Lester said. "There will come a time, it'll probably be a sneaky visit, I probably won't tell anybody, and we'll come up there and watch some games. I just want to come in there and enjoy being a fan and being at Fenway with my kids as a family. But we'll be around."

Enjoying retirement, satisfied with career

Not every professional athlete enjoys a smooth transition to retirement. It can be hard to move on and many struggle to fill the void left behind.

But since announcing his retirement this January after 16 big league seasons, Lester said he's had no such trouble adjusting to his new life.

"It's been good. I thought I'd go through a time where I'd miss it but I haven't done that yet," Lester said. "I've had a couple of times where I've gotten together with some guys I played with, guys I played against in different circumstances. That kind of filled the void of that camaraderie that guys say you miss more than the game. I think I've done a good job at that, I've got my kids that are running me around and staying busy, so it's been good so far."

Lester finished his career as one of the 21st century's most accomplished pitchers. He went 200-117 with a 3.66 ERA and 2,488 strikeouts for his career while playing an integral part in three World Series championships. He threw a no-hitter, earned five All-Star nods, finished top-5 in Cy Young voting three times and ranks near the top of effectively every major postseason pitching leaderboard. He also beat cancer.

That's quite a resume, one that will likely earn Lester consideration for the Hall of Fame once he's eligible five years from now.

Whether or not that happens, Lester says he's satisfied with his career. Being in the Hall of Fame conversation is nice, he said, but at the end of the day he accomplished everything he set out to do.

"If you have that brought up then you must have done something well along the way," Lester said. "I've said it and I stay consistent with it, I didn't play the game for that, I played the game to win championships and be a good teammate and pitch for a long time and I was able to do that.

"In five years if they make that call and I get the opportunity, if it's five years or ever, obviously I'd be one of the happiest people in the world," he continued. "But if it doesn't happen then it doesn't take anything away from the effort, the results or the satisfaction I got from my career. Either way I'm happy and more than satisfied with what I was able to do throughout my years."

Email: mcerullo@northofboston.com. Twitter: @MacCerullo.