Coolbaugh: After striking out on Yoshinobu Yamamoto, what will Red Sox do for starting pitching now?  taken at BSJ Headquarters (Red Sox)

(Photo by Denis Poroy/Getty Images)

Blake Snell #4 of the San Diego Padres walks off the field after pitching during the third inning of a baseball game against the Boston Red Sox at Petco Park on May 19, 2023 in San Diego, California.

No Shohei Ohtani, no Yoshinobu Yamamoto, no problem? Not exactly.

I was fully prepared to sit down late Thursday and write a column pondering what direction the Red Sox would go when they inevitably didn’t sign Yamamoto. Lo and behold, Yamamoto officially sealed Boston’s fate a few hours later when he agreed to sign a whopping 12-year, $325-million deal to team up with Ohtani on the Los Angeles Dodgers.

As with Ohtani, the only positive development for the Red Sox there is that Yamamoto won’t be pitching in the AL East for the New York Yankees. But that is of little consolation for a fan base disenchanted with their team that has now missed out on the top two free agents on the market this offseason.

So now what? In the coming days, we’ll likely hear the usual “we tried” leaks coming from the Red Sox camp. They made their $300 million offer (a reported offer that was later deemed “inaccurate”) and Yamamoto wasn’t buying. Hey, what can you do? *Shrugs in Craig Breslow

We will learn what John Henry’s team did or didn’t offer Yamamoto soon enough, but now our focus shifts to what the Red Sox will do now to address their starting pitching needs. Let’s take a look at the options on the table…

Blake Snell 

The obvious move now would be for Breslow to make a panic signing of the best remaining free-agent starter. That, of course, would be the reigning National League Cy Young Award winner: Blake Snell.

Any other year, a reigning multi-time Cy Young Award winner — one who is only the seventh player in major league history to win the award in both the American and National Leagues — would easily be the most-coveted free agent pitcher. Ohtani and Yamamoto surely stole the spotlight this offseason, but Snell’s skillset is nothing to sneeze at. The recently-turned 31-year-old southpaw is entering his ninth season with a reputation that precedes him. 

At a projected market value of just under $24 million annually (per Spotrac), Snell would definitely still qualify as a big-time signing and fill the Red Sox’s need for an ace. There’s no arguing that he would make the rotation better and push them closer to returning to contending status. However, if the Red Sox go this route, you can imagine what the posturing coming from inside the walls of Fenway Park will sound like. “We promised full throttle, and we delivered!” … “We view ourselves as contenders” … “the Red Sox are back!”

Not quite. It’s a hard sell to suggest that you truly went “full throttle” when you struck out on the top two free agents, both of whom are starting pitchers. Signing Snell alone should not be considered enough to satisfy ownership’s self-imposed expectations of going all out to resurrect the Red Sox. 

Another problem Henry and Breslow will encounter is those other pesky teams who were reportedly in on Yamamoto. It isn’t reasonable to expect that the Yankees, New York Mets and Philadelphia Phillies will simply pick up their ball and go home. They’re going to be in on Snell too, and that’s going to drive up the price even more. It wouldn’t be surprising to see a pitcher who is currently valued at around $25 million per year wind up getting a deal that pays him over $30 million annually after a bidding war.

And if spending $27 million a year was too rich for Henry’s blood with Yamamoto, I wouldn’t get my hopes up that he’ll be willing to spend on Snell. The only saving grace with Snell is that he’s 31 while Yamamoto is 25. Snell likely isn’t going to be getting a 12-year commitment like Yamamoto did, but it’s reasonable he could command a deal in the ballpark of seven years. At $30 million a pop, that’s still a $210 million contract. More realistic? Sure. But what have the Red Sox done lately to make us think that’s likely? 

Jordan Montgomery

While Snell would be the obvious next move, Montgomery seems to be the likeliest move for these Red Sox. And there’s a good chance Montgomery will be the only only significant signing of a starting pitcher in free agency by Breslow.

That’s a bummer. 

As I’ve written, Montgomery doesn’t profile as a true No. 1. But he’s better than nothing, and that might as well be the Red Sox’s new slogan. “Greg Weissert, better than nothing” … “Cooper Criswell, better than nothing” … “Jordan Montgomery, better than nothing.”

Montgomery’s salary projection by Spotrac is about $18.5 million. That’s probably more in Henry’s wheelhouse, but the same worry applies that teams that missed out on Yamamoto and Snell will be turning their attention to — and overpaying for — a defending World Series champion like Montgomery. If that happens and Montgomery’s value gets pushed into the mid-to-upper twenties, the Red Sox could be priced out once again.

Let’s hope his wife’s medical residency is off to a good start and they’re enjoying the holiday season in Chestnut Hill… 

(This feels silly to even suggest at this point, but if the Red Sox signed Snell AND Montgomery… that’s a different story. It’s a big if, I know. But it Breslow walks away from his first offseason at the helm with Snell and Montgomery in tow to pair with Chris Sale and Brayan Bello, that gives Boston a solid rotation to work with. Again, full throttle it is not, but it would be a step in the right direction.)

Clayton Kershaw?

Even considering his first-ballot Hall of Fame career, Clayton Kershaw should have only been seen as a “break glass in case of emergency” signing for a Red Sox team determined to make a slash this winter.

And yet, here we are…

Signing a three-time Cy Young Award winner and 10-time All-Star sounds pretty good on face value, but not when said signing is going to be 36 years old by the time Opening Day rolls around. 

Spotrac puts Kershaw’s market value at $37 million, albeit with the expectation that it’s only for one season. Would Henry pay that much for one pitcher if the commitment is only a year or two? Perhaps, but if the Red Sox have already missed out on Yamamoto, Snell AND Montgomery, then signing Kershaw feels like a waste of time. 

Unfortunately, that feels like exactly the kind of smoke and mirrors “big” signing that ownership would try to sell as a big deal. Frankly, Red Sox fans are smarter than that. 

After Kershaw, there are a number of cheaper options the team could pursue like Lucas Giolito, Brandon Woodruff, Marcus Stroman, Mike Clevinger and Hyun-Jin Ryu among others.

Oh, how the mighty have fallen… 

Gethin Coolbaugh is a contributor to Boston Sports Journal. Follow him @GethinCoolbaugh on X/Twitter and Instagram.

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