John Tomase

Red Sox thoughts that mostly make me want to cry

It hasn't been a particularly enjoyable offseason in Boston.

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Lots of Red Sox and (mostly) Red Sox-adjacent news to pick through from the last few days, so let's get up to speed ...

First come reports that Japanese left-hander Shōta Imanaga has agreed to terms with the Cubs on a deal that will pay him anywhere from two years and $30 million to multiple years and $80 million.

As usual, we will begin with our recurring lament: Where were the Red Sox? They had been linked to Imanaga all winter, with the bidding expected to surpass $100 million. Instead, he reportedly signed for less than the $85 million the Mets gave Kodai Senga last winter – a deal that went down as one of baseball's biggest bargains.

Imanaga didn't merit the attention of countryman Yoshinobu Yamamoto, who signed with the Dodgers for $325 million, but he was a standout in his own right, despite being a little undersized (5-foot-10, 176 pounds), and a little older (30).

He's a Statcast darling, thanks to his high spin rates and low walk rates, and there's a chance the Cubs just landed a solid No. 3 starter for entirely reasonable money. If the Red Sox couldn't beat that offer, why bother?

Our buddy Dan Shaughnessy of The Boston Globe has repeatedly lampooned the Red Sox for "being in on" everybody, a criticism I withheld after Craig Breslow's arrival and Tom Werner's Hall of Shame-worthy sound bite about going full throttle on the assumption that the new front office deserved a chance.

Shame on me. As the offseason ticks towards zero and the Red Sox remain sidelined for all but the most uninspiring transactions, it's clearer than ever that ownership's payroll restrictions are real, and so is the possibility of a wire-to-wire last-place season. ...

Along these lines, the courtship of Teoscar Hernández represents another head-scratcher. The slugging outfielder has put up monster numbers in Fenway Park and represented the perfect fit as a right-handed bat to slot between Rafael Devers and Triston Casas.

The fact that he could be had on a short-term deal made even more sense, but rather than lock him down for, say, two years and $40 million, the Red Sox watched him sign with the Dodgers for one year and $23.5 million, much of it deferred.

Maybe they'll pivot to Jorge Soler and receive similar production, but every potential target that signs elsewhere leaves them looking at iteratively worse substitutes. ...

Internally, per MassLive, the Red Sox have promoted Paul Toboni to assistant general manager, marking Breslow's first steps towards shaking up the front office. Toboni, who played at Cal, oversaw the first drafts of the Chaim Bloom era, landing Marcelo Mayer, Roman Anthony, and Nick Yorke, among others.

Toboni joins a crowded group of assistant GMs that includes long-time executives Raquel Ferreira and Eddie Romero, as well as more recent arrival Michael Groopman. When Breslow was hired, he promised to take a cold, hard look at the front office and embraced the idea of turnover. Toboni doesn't exactly fit that bill, since he's simply being promoted from within, but change has begun. ...

What exactly is wrong with signing Jordan Montgomery? The Red Sox don't seem interested in the big-ticket left-hander, preferring instead to add a controllable young arm to their rotation via trade. The issue is obviously money, but here's what I don't understand.

Acquiring someone like Jesus Luzardo from the Marlins or Dylan Cease from the White Sox will require parting with prospects, and good ones. The selling point is control, but Luzardo has three years before free agency and Cease two, whereas Montgomery would be under contract for a minimum of six years. That's team control, too, even if costs $25 million annually.

Why not sign Montgomery and keep your prospects, especially if this season clearly isn't on a championship trajectory either way?

It once again calls John Henry's priorities into question. If his primary goal is keeping the payroll middle-of-the-pack, then signing Montgomery from $150 million-plus is a nonstarter. If it's building for now and the future, then sign the guy who'll only cost money and won't even require you to fork over a draft pick.

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