Former Red Sox Ace Jon Lester Open to Reunion With Organization He Began Career With

Former Red Sox ace and current Cubs left-hander Jon Lester is open to a potential reunion with Boston this winter, he said in a radio interview with WEEI’s Rob Bradford.

Lester, who turns 37 in January, is entering the final year of the six-year, $155 million deal he signed with Chicago back in December 14. That contract includes a $25 million vesting option for 2021 if Lester were to pitch 200 innings this year or 400 innings between the 2019 and 2020 seasons. Even if those numbers wind up getting prorated due to the coronavirus-induced shutdown, it seems unlikely that he would reach that mark, thus making him a free agent later in the year.

“We’ve got a lot of what-if’s going on right now,” Lester told Bradford. “For me, I don’t know what is going to happen next year. I know I have the team option, the player option, that sort of thing. We’ll figure that out one way or the other. I will either be here or be a free agent. Obviously everything is open. I’m open-minded to anything.”

Drafted by Boston in the second round of the 2002 amateur draft out of Bellarmine High School in Tacoma, Wa., Lester won two World Series titles and made two All-Star teams in his first go-around with the Red Sox.

As you may recall, Sox brass famously low-balled Lester in the spring of 2014 as he was nearing free agency and coming off a 2013 campaign in which he was an All-Star, helped Boston win another World Series, and finished fourth in American League Cy Young voting.

At that time, principal owner John Henry and Co. offered the lefty a four-year, $70 million extension, good for an average annual value of $15 million.

Even after publicly expressing that he’d be willing to take a discount to keep the Red Sox as competitive as possible, that offer was still downright disrespectful, to be blunt. Especially when Lester had just seen the Yankees sign international free agent Masahiro Tanaka, then 25, to a seven-year, $155 million contract that January.

So after botching those extension talks, the Red Sox wound up dealing Lester to the Oakland Athletics prior to the 2014 trade deadline, and the Washington native went on to sign that aforementioned six-year deal with the Cubs a few months later.

As productive as Lester has been since joining the North Siders, his 2019 campaign was not the most memorable.

Starting 31 games, Lester posted a 4.46 ERA and 4.35 xFIP over 171 2/3 innings of work. Not terrible numbers by any means, but it certainly would appear that the southpaw is on the decline at this stage in his career.

Preferably, Lester would like to prove that last year was just a blip and not the way things are trending for him, but his chances to do that are growing slimmer and slimmer as each day passes with no plan for a 2020 season in place.

“On a personal level, this hurts me,” he said of the shutdown. “I’m not getting any younger and coming off a year like I had last year, this isn’t going to help me.”

Because of that uncertainty, I’m sure Lester has had more time to think about different things while waiting this pandemic out from his Georgia home, and it certainly seems like returning to Boston has crossed his mind more than once.

“Absolutely it would be cool to go back and finish my career where it all started,” he said. “But, I’ve got a little time before I really have to sit down and weigh that decision, even if it’s something where they want me back. Hopefully, I’m still a good enough caliber pitcher that the want of my services will still be out there for people. We’ll see.”

We will have to wait and see. I mean, who knows what the market for a veteran 37-year-old left-hander with 2,500+ innings under his belt will look like come free agency? How much would Red Sox chief baseball officer Chaim Bloom be willing to dish out for someone like that if he feels like Lester fits a team need? Both are unknowns at this point in time.

Author: Brendan Campbell

Blogging about the Boston Red Sox since April '17. Also support Tottenham Hotspur.

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