Red Sox

Since Red Sox Won’t Come to Their Senses and Keep Jon Lester, Here’s an Intriguing Destination


I hope Jon Lester throws every pitch of his major league career for the Boston Red Sox.

I hope, 10 years and another three championships from now, long after he’s blown past Roger Clemens and Cy Young atop the franchise’s victories list, he departs with a Mariano Rivera-style goodbye.

Imagine: Manager Dustin Pedroia, who played with Lester from their Single A days in 2004 until his own retirement in 2022, will come out to escort him from the mound, accompanied by veteran All-Stars Xander Bogaerts and Giancarlo Stanton, his two longest-tenured teammates.

There will be smiles, hugs, inside jokes outsiders like us would never understand, maybe a few tears, and later, probably a few beers. (Hold this chicken this time.) Lester will doff his cap as Fenway salutes him one final time as player. Then he’ll walk down the tunnel, his legacy as a one-team icon secure.

Of course, he’ll still have a postseason start or five left to make. Their best-of-9 first-round series against the Montreal Rays will begin the following week.

Yes, that would be one hell of an appropriate final scene. But we know better. Even a slightly less hyperbolic version isn’t going to happen.

We’ve already seen Lester’s final scene. The Red Sox pulled him from his start tonight — John Farrell, forever his advocate, looked just thrilled to make that announcement — and so his final scene has already been wrapped.

Let the record show his final act as a Red Sox pitcher was retiring the Rays’ James Loney on a sixth-inning popup to shortstop Friday night at Tropicana Field. Hardly dramatic, huh? The Rays haven’t even moved to Montreal yet.


Right now, the goofy daydreams are more fun than reality. Jon Lester is going to get traded. It’s a matter of when he’s traded — I expect the news to break at 4:03 p.m. Thursday, minutes after the passing of the trade deadline and right when we’re about to exhale — and where he’s headed.

I don’t want to see him go. I think the steadfast refusal to commit long-term deals to players older than 30 is counterproductive — the ability to do so, to risk a bad deal in the long-term to retain a player who is doing everything right, is one of their advantages.

But I’m resigned to it, and I’ll admit, I’m curious to see what they get in return.

I don’t particularly care where he ends up, whether it’s one of the oft-rumored destinations such as Los Angeles, Pittsburgh, Milwaukee or roughly a half-dozen other franchises. I just want to see the Red Sox get an elite prospect, at the minimum, in return. Hopefully one who will hold great appeal to the Miami Marlins in a year or so.

For a franchise hungry to win a championship, a rental of Lester is worth the steep price. And who knows, maybe he’ll stick around at his new baseball home beyond the season.

Anyone who thinks he’s coming back here, when multiple teams will be bidding and the sticker price will be more than twice what the Red Sox offered in spring training, is either in denial or flat-out delusional. They’re not paying him now. They won’t pay him when the price has grown even more.


There is one potential destination that strikes me as more interesting than the others: Baltimore. There is the Dan Duquette factor, obviously. He must be savoring watching his first-place Orioles rise about the Red Sox in the standings. For him, it is redemption. Surely that would be even sweeter if he can pluck away the Red Sox’ ace along the way, and his Orioles have a distinct need for a pitcher of Lester’s magnitude.

I hadn’t considered this until I read Jayson Stark’s thorough Lester column yesterday, but there really should be no concern about trading within the division. The Red Sox probably have a strong sense for where Lester prefers to pitch, and chances are Baltimore isn’t atop his list of potential baseball homes for the next half-dozen seasons. As one unnamed executive told Stark:

I could even argue that you should always trade rentals in your division, if you think they’re not going to sign there, because you take their prospects away.”

The question is whether he will part with one of the Orioles’ prized pitching prospects — Dylan Bundy, Kevin Gausman, and Hunter Harvey — to acquire the pitcher he needs right now. He should. The Orioles have a chance. That’s a rare occurrence in this division, and he needs to seize the moment.

Duquette acquired a couple of future Red Sox cornerstones — Jason Varitek and Derek Lowe — for the Red Sox right around this date in 1997.

Provided that no other franchise trumps the offer, maybe he’ll deliver another generation’s cornerstone or two to Boston by tomorrow evening.

But man, that great potential ending for Jon Lester in mind, it’s hard to fathom that this is what it has come to — hoping Dan Duquette sends prospects to the Red Sox for a player no one wants to see go.


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