The Dodgers have done it again. After a two-week long saga of meetings and contract offers, the Dodgers had the final say in the Yoshinobu Yamamoto sweepstakes, matching the New York Mets offer to sign him to a 12 year, $325 million deal.

Yamamoto’s signing is significant to the Red Sox for multiple reasons. Whether the Red Sox had a chance or not (reports were conflicting), Yamamoto was Boston’s top priority headed into Winter Meetings at the start of the month and remained their top priority throughout this month. Their top priority is now off the board. While that doesn’t automatically make this off-season a failure for the Red Sox, the pressure is on for them to make a move. 

With Yamamoto off the board, the market is expected to begin “thawing”, in the words of MLB insider Mark Feinsand. Dominos are going to begin falling off the board, and the Red Sox will have to act fast to land them.

This is one of the most important, if not the most important Red Sox off-seasons in my memory. After two seasons in the purgatory of mediocrity despite a developing young core, Red Sox owners Sam Kennedy and Tom Werner as well as GM Craig Breslow promised that this team was ready to go “full throttle” towards winning championships. They set the bar high, and as a big market team, they should be able to live up to it.

Thus far, Breslow and the Sox have yet to prove the doubters wrong. Many fans continue to blame the front office. While it’s unclear what caused the Red Sox to miss out on Yamamoto, the reputation they have gained over the last few years (not to mention the doubt of the fanbase compared to other fanbases) does not help their case on convincing Yamamoto to come here. At the end of the day though, Yamamoto wanted to be a Dodger, and the Red Sox cannot control that. What they can control is how they react and pivot. This upcoming stretch is where the offseason will be won or lost. If they truly were in the bidding for Yamamoto, that means they had $300 million they were willing to spend this offseason. Where is that $300 million going to go now?

In order to see significant improvement, it will be necessary to add two more starting pitchers, with at least one of those two being definitively better than anyone the Red Sox currently have on the roster. You could argue that in order to really compete in this tough AL East, two high-end starters will be necessary. They’ll also need a right-handed bat, preferably one who can slot into the top six of their lineup. It remains to be seen whether Tyler O’Neill can be trusted in the top six of a contending lineup, and I would feel most comfortable with him in the bottom third of the lineup. 

It’s clear that improvements need to be made. The question is whether they will get there, and if so, how?

Signing World Series hero Jordan Montgomery would be a great start. The Sox are the only other team outside of the Rangers who have shown clear interest in Montgomery.

However, interest has not done the Red Sox much good in recent years. This fanbase needs to see actions to back up the team’s words, and there’s no reason this deal should not get done.

Montgomery is reportedly spending the winter in Boston as his wife completes residency at a local hospital. It seems likely that Montgomery would be interested in staying in Boston beyond this winter. While other big market teams could get involved with their own money to spend after missing on Yamamoto, Montgomery is unique from other free agents in the fact that the Red Sox may not need to blow away competitors with more recent success to get him. Per MLB insider Bob Nightengale, “The Red Sox may have a slight edge in signing free agent Jordan Montgomery, who moved to Boston this winter where his wife started a dermatology residency at a local hospital.” I would expect Montgomery to come here as long as the Red Sox can match the offers around them, similar to how the Dodgers matched Yamamoto’s highest offer. There is zero excuse not to do so. 

Montgomery would be a great start in righting the ship for the Red Sox, improving their reputation as well as their on-field success. However, Montgomery alone will not bring this team back to glory. He would only be the first piece of a successful Red Sox offseason.

The Red Sox’s offseason will be judged not just by whether they land Montgomery, but also what they’re able to do around him. If you land another high level starter alongside him like Blake Snell, Corbin Burnes, or Shane Bieber and add an all-around second baseman such as Ha-Seong Kim, I’d call that a sweeping success. If they don’t land a second arm or neglect to add another bat, that won’t be enough. The likelihood is the outcome will fall somewhere in between those two scenarios.

I would personally predict one high-level starter (likely Montgomery) alongside a reunion with James Paxton and the signing of 2B/OF Whit Merrifield. This would be a solid offseason for the Red Sox, but it’s unclear whether it would be enough to get them over the edge. You would have to rely on the younger players to take a step up and lift them back to the playoffs.

In order to control their own destiny, the Red Sox should put forth their best effort to land not just one, but multiple big names via free agency or trade. Anything short of that effort would be a failure. Inability to find a way to fill the needs of two starting pitchers and a right-handed bat would also be a failure. While the Red Sox haven’t failed this off-season yet, they have something to prove, and now is the time to do something about it.