Mookie Betts Signing Back With the Red Sox in 2021 Isn’t as Absurd as Some Think

Mookie Betts is a free agent following the 2020 season. The Red Sox will have the spending room to sign a big free agent. Let's talk.


On Monday, the Mookie Betts trade version 2.0 was announced. Betts and veteran starting arm David Price were dealt to the Los Angeles Dodgers in exchange for highly regarded prospects Alex Verdugo, infielder Jeter Downs, and catcher Connor Wong.

Since Betts was sent packing to LA alongside David Price–who you have to imagine was elated to get the hell out of Boston–the discussion has really shifted to what he could do following the 2020 season.

We’ve been gearing up for the monstrous contract that he’ll inevitably receive, but the only questions that remain are who will be giving him that deal, and for how much?

The Red Sox final offer for an extension to Betts was for 10-years, $300 million. And Betts then reportedly countered that offer with 12-years, $420 million. It goes without saying that these two ideas of a deal were miles apart. But I think both sides of the negotiation knew that unless Boston put an offer on the table that would be ridiculous for Betts to refuse, the 2018 MVP was going to find himself on the free-agent market. And honestly, good for him. He absolutely should, because when the ink drys in whichever ballclub he’s in, he’ll be happy that he waited it out.

Betts has been hellbent on landing himself in free agency. And I’d have to expect that this notion only became more clear after seeing the numbers that were thrown around ahead of the 2019 season for Mike Trout, Bryce Harper, and Manny Machado. And seeing those three names of some of the best players in baseball, Betts should find himself tailing only Trout in his earnings.

Because of the reluctancy to get an extension done like fellow Red Sox homegrown talent, Xander Bogaerts, it’s obvious that Betts’ gameplan is to bring him the biggest bag of cash that he possibly can. And the only way to do that is to test the market and see which organization will offer what, in their courting of the outfielder next winter.

Blinded by rage, anger, and disgust, mostly directed at Red Sox ownership, some people have ignored the fact that in making this deal, Boston set themselves up to land a big offseason acquisition in let’s say, free agency, following this upcoming season.

Whether or not you believe it was a mandate for the Red Sox to get themselves below the $208 million luxury tax threshold in order to reset their luxury tax penalties is a moot point. The front office made it known that this was their initial goal very early on in the offseason and if they didn’t want to make this a top priority, they wouldn’t have come out and directly had this excuse to trade one of the best players in baseball setup and placed directly in front of our faces.

But in the grand scheme of things, they dealt Betts and former Cy Young winner, Price, to reset those aforementioned penalties and have a payroll that’s sitting pretty at about $196.27 million, according to Red Sox Payroll on Twitter. Unless they decide to go rogue and start trading for guys with major salaries at some point during the season, they’ll get those numbers reset relatively easily. Well, if you count trading one of the best players in the game today as “easy”.

Even with the addition of an expected “frugal” Chaim Bloom to the front office, Boston likes to spend and they like to spend big. Perhaps it won’t be as irresponsible and chaotic as it was with former President of Baseball Operations, Dave Dombrowski, but if John Henry wants to put a winning product out onto the field while at the same time, reconstructing some of the nasty PR that’s come along with this offseason, they should make a serious run at Mookie Betts ahead of the 2021 season.

They’re in a position now to pursue Betts and offer him a contract that will, well, should, compete with some of the other high bidders. An ideal contract would be something sitting at 10-years, $350 million, but no higher, at least in regard to years.

Look, Betts’ counter offer that was mentioned earlier was for $420 million over a span of 12-years. That brings his AAV to $35 million a year. And honestly, that’s a beautiful number that John Henry should be more than happy to sign when it comes to Betts. So that 10-year, $350 million mark brings you to the same AAV. And that’s an offer that Betts should at least ponder, as long as there’s not a team that’s seeing red and is ready to throw the entire organization and the key to the city at him. Most people want Betts back, but 12-years is flat out irresponsible. Those extra two years do make an incredible difference, especially if we start to see Betts and his small frame start to break down around year number eight which is a distinct possibility.

And coupled with the Red Sox financial flexibility, is the mere fact that he reportedly did like Boston and wanted to stay.

According to Jim Rice on MLB Network Radio, Betts called Boston “home” and said that he didn’t want to go “anyplace else”.

There was widespread speculation about whether or not Betts did actually enjoy his time in Boston. For whatever reason, the idea was that he actually didn’t like being with this ballclub in this city, although he never came out and said that. As it turns out, that could have just been a media-driven concept which–duh.

He already has an attachment to not only the Boston Red Sox organization, but to the guys inside that clubhouse as well.

In Fort Myers, Florida at Red Sox spring training, shortstop Xander Bogaerts didn’t necessarily brush away the thought of trying to recruit Betts back to Boston, according to Chris Cotillo of

When speaking on Betts, Bogaerts said that Betts knows what he means to him and his teammates.

“Hey, you know… probably, maybe in a year. We’ll see how that goes. He knows what he means to us and we’ll cross that bridge when we get there.”

Bogaerts even touched on the matter of the belief that Betts didn’t want to be in Boston for the long haul.

“The one thing I know about him is that he loved being here. He enjoyed playing with us. He was a great teammate. I can’t really say that he didn’t want to be here. I think that’s a little unfair. He enjoyed his time here and never showed me anything he didn’t like about being here. It’s going to be tough without him.”

The Red Sox have a lot working in their favor. The resounding belief appears to be that Betts won’t be back in a Red Sox uniform following this upcoming season where he’ll be wearing Dodger blue. But I think there’s a greater chance than what many others believe.

Why rule out the Red Sox when the consensus thought is that he’ll end up with whichever team throws the most amount of cash his way? Again, to reiterate, Boston has lined themselves up by trading him this offseason so they then can go and sign a free agent to a large deal following the 2020 campaign. And one of those potential free agents is one, Markus Lynn Betts.

Because many are under that same assumption, it might come down to whether or not the Red Sox are willing to offer up that kind of deal. Especially when down the line, you have to think about other potential contracts that a deal of that magnitude may prevent such as up and coming superstar, Rafael Devers, who really proved last season that he’s the real deal.

John Henry and Tom Werner didn’t bring in Chaim Bloom to do the exact same thing that Dombrowski did and construct a mountain of a payroll. Bloom’s here to be cautious and calculated with trades and signings, much like they were in Tampa Bay. A club that beat you out in the standings with a $60 million payroll.

The chances may not be anything eye-popping, but if Betts is going to end up with the organization willing to give up the most money, why are the Red Sox suddenly not right up there as favorites to sign him? I’ve got a shirt coming in the mail as we speak from Barstool Sports that says “Pay Mookie 2021”. And that is a slogan Red Sox nation should take on the moment the final out of the 2020 World Series is recorded.

If Bloom does find a way to sign Mookie Betts, then he committed a highway robbery of the Los Angeles Dodgers with the return they brought back.

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