Jon Lester looks back on a unique career with Sox, Cubs

July 4—CHICAGO — No one has ever had a career quite like Jon Lester’s.

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

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

Lester’s experience was truly unique.

This weekend, the Red Sox and Cubs will face each other at Wrigley Field for a rare three-game run, and if anyone can understand what this matchup means, it’s Lester. Having started his career in Boston before becoming arguably the greatest free agent in Chicago history, he has a unique understanding of the two historic franchises, their storied home baseball parks and passionate fan bases.

“Every time historic franchises play against each other it’s a cool deal. I was spoiled to play against the Yankees with the Red Sox so many times,” Lester said Friday night. “Every time you develop that much history, it adds a little bit 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 talked about 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 how many great moments he was a part of during his career.

As a 23-year-old boy, he took the series win in the 2007 World Series just months after beating cancer.

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

Three years later, he fulfilled his promise by signing with Chicago, helping the Cubs finally break their age-old curse and win the 2016 World Series. Any one of those achievements would be a crowning achievement for most players, but for Lester it’s impossible to compare the three titles as they each came at such different times in his life and career.

“Coming back from cancer in ’07 and being a part of that was a really unique and different experience for me and getting the chance to pitch, be a young guy, be around the older guys and see how it’s done,” Lester said. . “And ’13 is the guy that is trusted in Game 1 and Game 5 and gives a good start and gives our team a chance to win and set the tone. Kind of being trusted.

“And then sign to a team that hasn’t won in 108 years and you’re supposed to be the person signing 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 before the other, just based on different points in my career and personal points in my career.”

No hard feelings about turbulent Sox exit

For all the success Lester enjoyed in Boston, few would blame him if he held a grudge against the Red Sox for the way the club handled his departure. In the months since Lester starred in the 2013 World Series title run, the Red Sox front office mishandled his contract negotiations, eventually swapping him for the Oakland Athletics on the 2014 trade deadline.

Although it was difficult at the time, Lester said it hasn’t and that he has nothing but love for the organization.

“I love the Red Sox. I think when you grow and you mature and you understand the game and you understand the business of the game, you understand that decisions have to be made, whether they’re hard or easy,” he said. Lester. “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.

“Back then it was hard, but like I said, as you get older, you understand things and you understand that’s part of what happens,” he continued. “I will always love the Red Sox, they gave me the chance to become a big leaguer, not just to become a big leaguer, but to become a Pro and then a big leaguer, then gave me the chance to cast for a significant amount of time and I was able to take it from there Not only that but how they treated my family and me when I went through all my stuff in ’06 and ’07. There were a lot of positives, more than just getting traded out.”

Eventually, Lester hopes to return to Boston, noting that his children weren’t old enough to remember seeing him pitch there. At some point, he’ll probably fly up with his family for a weekend getaway, though fans probably won’t hear about it if they do.

“We’ve been talking about picking them up and doing the whole Boston tour and seeing a few games,” Lester said. “There will come a time, it will probably be a sneaky visit, I probably won’t tell anyone, and we’ll come over there to watch some games. I just want to get in there and enjoy being a fan and being in Fenway with my kids as a family. But we’ll be there.”

Enjoying retirement, satisfied with career

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

But since announcing his retirement in January after 16 big league seasons, Lester said he hasn’t had much 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 yet,” Lester said. “I’ve had a few times where I got together with some guys I played with, guys I played against in different circumstances. That filled the void of that camaraderie that guys say you miss more than the game. I think I I’ve done a good job in that, I’ve got my kids running around and keeping me busy, so it’s been good so far.”

Lester finished his career as one of the most accomplished pitchers of the 21st century. He went 200-117 with a 3.66 ERA and 2,488 career strikeouts while playing integral in three World Series championships. He threw a no-hitter, earned five All-Star nods, finished in the top-5 three times in Cy Young votes, and is nearly at the top of every major post-season pitching standings. He also beat cancer.

That’s quite a resume, one that Lester will likely consider for the Hall of Fame once he’s eligible in five years.

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

“If you brought that up, you must have done something right along the way,” Lester said. “I’ve said it and I’m going to stick with it consistently. 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 .

“If they make that phone call and I get the chance, if it’s five years or ever, of course in five years I’d be one of the happiest people in the world,” he continued. “But if it doesn’t happen, it won’t affect the effort, the results or the satisfaction I’ve gotten from my career. Anyway, I’m happy and more than satisfied with what I’ve been able to do throughout my career. ” year.”

E-mail: [email protected]† Twitter: @MacCerullo.

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