Jon Lester helped the Red Sox win two World Series during his nine years in Boston. He went 1-0 in the 2007 Fall Classic and 2-0 in 2013, the year before Boston traded him at the deadline.
Lester went on to sign in free agency with the Chicago Cubs, where he won a third World Series championship in 2016. However, the lefthander may have stayed in Boston for the long haul had he not been dealt to Oakland in 2014.
Lester told Audacy’s “The Bradfo Sho” about how the trade opened his eyes and sent a message to the baseball world about his future, a future that he could’ve had in Boston.
“When you’re able to go to another city and another community and make a home and realize that baseball’s baseball… It helped me realize that the grass can be greener on the other side and if you don’t know that you’re always gonna stick on your side of the yard,” Lester said (13:20 in player above).
“In my instance I would always lean towards Boston. Any time I would talk about Chicago or San Francisco or whoever, I’d always come ‘Well Boston has this’ or ‘Boston is this’ or ‘I know these people there. I know the Spring Training facility.’ It was always coming back to comfort.”
Despite Lester’s success in Boston, contract negotiations stalled in the 2014 season. The southpaw was in the final year of his contract and was traded to the Athletics at the deadline.
If Lester wasn’t moved at the deadline, it’s likely that he would’ve spent his entire career in Boston.
“I would think so,” Lester said. “Especially a guy like Theo (Epstein), those guys would think that I’m not leaving Boston so they’re not really gonna put the full-court press on you. I feel like when I got traded it kinda sent out a signal like I’m not coming back to Boston in the baseball world. I think if you stay there and you stay until you get to free agency, like I was saying earlier it becomes harder to leave that comfort. I think other teams aren’t gonna put that full-court – and everybody knew I wanted to stay. I made that vocal. I made that very clear.
“I think that if I would’ve finished out that year I don’t think the amount of offers and the amount of interest would’ve been there as me going to Oakland. I can’t go back and say I would’ve ended up staying because Chicago still could’ve come in and done what they did or another team did what Chicago did. But I think if you end up staying out that whole year it still becomes a little bit harder to leave.”
This is particularly of interest to Red Sox fans due to the looming free agency for Xander Bogaerts and Rafael Devers in the next two years.
“A guy like Bogey and a guy like Devers who have made some money, at the end of the day, man, when it comes down to when you want to stay somewhere it’s not always about the bottom dollar,” Lester said. “You treat these guys fairly. You treat them with respect. You handle the situation correctly. They’re gonna end up taking less money.”
There are going to be players that fall on both sides of the fence, but treating them like human beings and not just the number on their back goes a long way.
“There’s always gonna be someone that wants the bottom dollar, and that’s fine, that’s your prerogative, but the other majority I think is like ‘Hey man, listen, you treat me fairly, you do this respectfully, I’ll come your way you come my way.”