What on earth are the Red Sox doing?

6 min readDec 8, 2022


Jon Lester cashed in for $155 million over six years when he signed with the Chicago Cubs in 2014. The offseason prior, Boston offered Lester $70 million over 4 years to remain in Boston. He declined, and four months later he was traded to Oakland. There was certainly a middle ground between Lester’s $155 million with Chicago and the $70 million offered by Boston. Two years later, Boston shelled out $217 million over 7 years to David Price. Between 2016 and 2019, Price tossed 588 innings of 3.84 ERA ball for Boston. He had a respectable 1.20 WHIP and 3.74 FIP. He struggled in big moments but redeemed himself during the 2018 postseason. In total, Price logged 36 postseason innings with Boston to the tune of a 3.75 ERA.

Lester, during that same time span, logged 736.67 regular season innings in Chicago. He posted a 3.59 ERA, 1.28 WHIP and 4.02 FIP. In the postseason, Lester logged 70 innings with a 2.44 ERA.

Both players won a World Series title. Both signings paid off. Boston had to pay an extra $62 million, at minimum, for similar production and a title.

John Henry told us they botched the Lester negotiations. He’ll eventually tell you they botched negotiations with Xander Bogaerts, too.

Should they have matched San Diego’s ungodly 11-year, $280 million offer? No. Should Bogaerts have been able to be approached by other teams in the first place? Also no. Both can be true.

Scott Boras, Bogaerts agent, wants his guys to hit the open market. This isn’t a new trend — it’s how it normally plays out. Bryce Harper? Market. Gerrit Cole? Market. Stephen Strasburg? Market. Anthony Rendon? Market. Kris Bryant? Market. Hyun-Jin Ryu? Market. Some have signed extensions in the spring, though, when the value made sense. Lance McCullers inked a 5-year, $85 million extension. Jose Altuve landed a 7-year, $163.5 million contract. That Altuve extension breaks down to roughly $23.5 million a year — Bogaerts should have been offered a similar extension, if not a few million per year more.

A 4-year, $90 million extension did not cut it. Why would it have? It was less than the team paid to bring in Trevor Story (6 years, $140 million). It ticked off Bogaerts. Would 5–7 years and $150-$190 million gotten the deal done? Probably. The AAV should have been no less than $25 million, nor would it have required more than $30 million. They didn’t need to give him 11 years — no one knew about San Diego’s desperation to add yet another star last spring. They weren’t bidding against anyone else — just themselves.

With Bogaerts gone, they need another bat. Whether it’s a shortstop, or an outfield (moving Kike’ Hernandez to the infield), they need to add someone impactful. They’re linked to Carlos Correa and Dansby Swanson, the top two shortstops left on the market. Correa signed a 3-year, $105.3 million pact with Minnesota last year. He was able to opt-out and hit the market again this year. He’ll be seeking longer term for a similar AAV. If Boston wants him, they’ll have to compete with San Francisco, the Cubs, Minnesota and perhaps the Yankees. The price will go up. If Bogaerts landed $270 over 11 years, Correa, a year younger, will command similar term and money. He could get as much $250 over 10 years. Maybe $200 over 8. If they land Correa, it’ll undoubtedly cost more than it would have to keep Bogaerts around last spring.

Will we see a similar playbook unfold with Rafael Devers? Probably. I’d bet on it (though I suck at gambling so perhaps there’s hope). Extending in-house talents doesn’t come easy for this organization. Devers could possibly command 10 years and somewhere beyond $300 million. For a front office unwilling to go beyond 6 years and commit market value to all-star players, it’s difficult to envision a scenario in which Devers remains in Boston long-term.

There’s other needs on the roster, with or without Bogaerts. They’re in need of a front-end starter. They need a shortstop/second baseman/center fielder (depending on player alignment) and an everyday catcher. They’re banking on a rookie to handle first base duties and they brought in an on-base machine from Japan who, if he’s not DH-ing, will cement himself as a defensive liability in one of the league’s toughest outfields. So they’ll need a DH or a corner outfielder, too.

Bloom wants a “starter with upside”. They negotiated with Andrew Heaney and Zach Eflin. They offered larger deals than Texas and Tampa Bay, respectively, but both chose to sign closer to home. Heaney has pitched 707 major league innings. He has a career 4.56 ERA and 4.38 FIP. He’s coming off the best season of his career with the Dodgers (72 2/3 innings of 3.10 ERA/3.75 FIP ball), but at 31 one has to ask: exactly what is the upside?

Same with Eflin. He’s 28 going on 29 and was in Philadelphia’s bullpen during their postseason run this year. In 659 1/3 career innings, he’s amassed a 4.49 ERA, 4.36 FIP and 1.295 WHIP. Even if you take out his disastrous first two pro seasons (5.85 ERA and 5.79 FIP in 127 2/3 innings) we’re still looking at a 4.16 ERA and 4.02 FIP. Far from front-end numbers. There isn’t a front-end arm on the staff. Relying on Chris Sale is like planning a cross-country road trip and hoping a 1993 Honda Accord with 215,000 miles gets you from Boston to Los Angeles. Eflin and Heaney have only topped 150 innings one time a piece. You’d ideally want 30 starts and at least 5 innings per start — neither is getting you that consistently, if at all.

Do they get into a bidding war for Carlos Rodon? Do they finagle a trade for Shane Bieber or Pablo Lopez? Do they dip into the Pacific waters again and bring in Kodai Senga? In all likelihood, there’s a better chance of a pig flying out of Chris Christie’s ass.

They’ve targeted two marginal starting pitcher upgrades and failed to land either. Expecting them to exhaust resources for anyone of substance in the rotation doesn’t align with their approach to-date.

Yes, they’ve improved the bullpen — Kenley Jansen and Chris Martin give them proven late inning arms and they allow Matt Barnes and Jon Schreiber to avoid dog-days-of-summer burnout. They’ve excelled at building the backend of the pen (and no, that doesn’t count Joely Rodriguez who provides them with mop-up value), so credit where credits due.

Masataka Yoshida fills their leadoff spot, but he’ll likely be limited to DH duties if his fielding is as questionable as reports from Japan indicate. From the sounds of it they’d be better off sticking him out there with a flare gun and a fishing net than a glove. Yet that combination of getting on-base and fielding like a blind man costs 5 years and $105 million ($90 million contract, $15 million posting fee) coming out to $21 million a year.

Last spring, they offered the face of their franchise 4 years, $90 million — $22.5 million a year. Keeping Bogaerts in-town was always their top verbal priority, yet their actions speak differently. Their actions are that of a team shopping in the middle of the market. They’ll toss around 5 or 6 years, and $20 million per, but that’s where it caps. Story’s $23.33 million AAV may very well be the biggest on payroll when Sale’s contract expires. The days of Boston taking the plunge might be over, at least temporarily. Or they’ll pivot out of desperation and overpay on someone outside the organization. Either way, it’s lining up to be a disaster




I don’t know what to do, I know what not to do.