Dear John,

I am 52 years old, the same age you were when you bought the Boston Red Sox. That parallel has been on my mind lately, because at 52, you changed the trajectory of a franchise and, in a very real way, the emotional lives of millions of fans like me.

My father passed away in 2021. Because of the choices you, Larry Lucchino, and Tom Werner made, he and I were able to share something we never thought we would see together: a winning Red Sox team.

For most of my dad’s adult life, and for the first 30 years of mine, we lived with the assumption that the Red Sox simply did not win titles. We hoped, we joked, we endured heartbreak, but deep down we accepted that it might never happen — and if it did, it would be in an alternate dimension or something.

Then it happened. It really happened. Not once, but four times.

Those championships were not abstract achievements. They were nights on the couch, phone calls, laughter, disbelief, and relief. They were memories I still carry now that my father is gone. That is something no owner can ever fully measure, and something no fan should forget.

For that, you deserve real thanks.

When you bought the Boston Red Sox, you were a disruptor with conviction, appetite for risk, and a clear belief that bold decisions could rewrite history. You proved it.

You are 76 now. Time changes all of us. I don’t mean to get overly clinical — I’m a copywriter who does a lot of work in the healthcare space — but research is clear that as we age, dopamine levels naturally decline, and with that comes a shift in how we assess risk. Fewer decisions are driven by the upside of reward. More are shaped by the fear of loss. That is human. It is understandable. But it is also visible.

It is also fair to say that some of your ownership group’s old fire may be gone in the wake of Larry Lucchino’s passing. He left a real void in that department. You, Larry, and Tom Werner were a formidable force. Together, you changed baseball in Boston forever.

Sadly, your recent Red Sox teams have instead felt managed to avoid mistakes, not built to chase greatness.

In light of Alex Bregman’s regrettable departure for Chicago, I would like to propose that you sign Bo Bichette. Give him an eight-year, $320 million contract. Maybe that’ll do it. If he wants 10 years, give him 10 years. Give him what it takes. If the deal turns out to be an overpay, consider it a self-imposed tax for failing, in recent years, to be aggressive enough to win the way you once were.

What is the real risk in a deal like that? How involved do you realistically expect to be with this team at the end of that deal, when you are 84 years old?

If Bo Bichette can’t be acquired, please pursue any and all other similarly aggressive avenues to improve this baseball team. Championships are not won by protecting balance sheets. They are won by conviction. And by good baseball players.

Baseball is a game of failure. Not every deal will work out. Even some of the best teams fail to win it all. But if you are concerned with your legacy, which is worse: Trying to win, but failing? Or losing interest in even trying?

This is not a criticism as much as it’s a plea for clarity.

Red Sox fans love the Red Sox. We always have. We always will.

Do you still?

Regards,

Bill Colrus
(AKA @SawxSouth)

Before the Sonny Gray trade, virtually all talk about the Red Sox acquiring a #1A/#2 starting pitcher revolved around them making a trade to acquire that pitcher. It was also widely discussed that that trade would have to involve talent from the Red Sox’ MLB roster (see: Jarren Duran, Wilyer Abreu, and/or Ceddanne Rafaela) plus other pieces/prospects.

This trade would be for a younger starting pitcher that the team would hope to extend, not a 36-year-old starter that a struggling team was looking to unload and that would only be on the roster for a year.

From a money standpoint, Sonny Gray is essentially Lucas Giolito/Walker Buehler 2.0. Performance-wise, he will be an upgrade over both. The money we’re paying him will be off the books when any extension we give to another, higher-end acquisition kicks in.

While it is now less likely that the Red Sox will go out and sign, say, Dylan Cease or Framber Valdez for that #1A/#2 guy — I fully expect the bulk of their FA spending to be on bats (and a relief arm?) — the team still very much has the pieces to trade for higher-end starter. (Nobody ever viewed Fitts and Clarke as untouchable, and moving them didn’t significantly deplete the pool of tradable assets.)

I’m not saying this will happen. I’m just saying it can.

Deals seldom happen in the order we think they will or want them to happen, and a GM’s* words — or the “signals” reporters are getting from him — should always be taken with a grain of salt. Especially with a GM like Craig Breslow, who is still a work in progress when it comes to messaging. (Which is problematic in a toxic media city like Boston. But I digress...)

When it comes to making deals, it’s always better for a GM to say less rather than more. Sox fans who don’t love this deal, aren’t really upset about the deal, per se, but upset with the deal in light of Breslow’s earlier comments about the team’s supposed plans.

I would wager that Breslow’s more vague/sorta noncommittal comments *after* the trade are more reflective of the team’s actual plans. I would also wager that he wishes his earlier messaging was closer to what he said yesterday.

Regardless, folks are going to believe what they want to believe, and I suppose I am no different. But I am also an optimist.

It’s only November 26. We’ve barely made any moves, but I like what we’ve done so far. Let’s do more.

Happy Thanksgiving, everyone.

(*Yes, I know Craig Breslow is technically the Chief Baseball Officer of the Boston Red Sox, but typing “GM” is quicker.)