Jon Lester, now that you’ve retired from a storied big-league career, what are you doing next?
“The only plans I’ve got is I’m going to Orlando on Saturday, doing Disney for a couple days,” Lester said Wednesday on the Cubs Talk Podcast, “and then I’ve got a golf tournament next weekend.”
And maybe a trip to Cooperstown won’t be too far behind.
Lester, a five-time All-Star and three-time champion, was asked about the Hall of Fame many times the last few years of his decorated career but was reluctant to talk about it.
Now that he’s retired?
“I wouldn’t turn down the invitation if it was given to me,” Lester said. “I’ll put it that way.”
There's certainly a case that can be made.
Lester picked up his 200th career win last September — becoming the 119th pitcher in MLB history to reach the milestone. He’s only the 30th lefty to do so.
Three-hundred wins has long been considered a Hall of Fame benchmark. Considering how starting pitcher usage has changed over the last decade or so, reaching the 200 mark is noteworthy.
The only active pitchers with more wins than Lester are Justin Verlander (226) and Zack Greinke (219)
“The milestone of 300 wins is almost, the way the game is played now, and the way things are done, it's just different,” said Tommy Hottovy, Lester’s pitching coach with the Cubs from 2019-20, in September.
“It’s going to be harder for guys to get 300 wins.”
Lester was one of the most durable pitchers of his generation, making 30 or more starts 12 times. He tallied 2,488 strikeouts, retiring 40th all-time in that category, and finished with a career 3.66 ERA.
As NBC Sports Chicago's David Kaplan pointed out on the podcast, Lester is one of 33 pitchers ever to win 200 games, register 2,400+ strikeouts and finish with a sub-3.70 ERA. Twenty-four of those pitchers are in the Hall.
“I'll say this, I didn't start to play the game for the Hall of Fame,” Lester said. “Now that I'm officially done with it, if it came my way, if I did get that phone call and however many years it is, you would talk about probably one of the happiest people on the face of the planet.
“But if it never came, I'd be OK with it. I didn't play the game for that reason; I played it to win.”
Not only did Lester win the World Series three times, including when the Cubs won their first title in 108 years, but he was one of the most prolific postseason pitchers ever.
In 26 playoff appearances (22 starts) between the Red Sox, A’s and Cubs, he posted a 2.51 ERA, including a 1.77 ERA in six Fall Classic games (five starts). He was named co-MVP of the 2016 NLCS.
He's fifth all-time in postseason Win Probability Added, behind Mariano Rivera, Curt Schilling, John Smoltz and Andy Pettitte, and ninth in postseason innings pitched all-time (154).
“Those three World Series mean more to me than anything, those memories with those guys and those teams,” Lester said.
Lester didn't win a Cy Young award, finishing top-10 in voting four times, including a runner-up finish with the Cubs in 2016.
He's likely a borderline candidate but his postseason success will have him in the conversation when he joins the ballot in five years.
And if he eventually gets the call?
"I would be the happiest human being in the world if I did get that phone call," Lester said.