MLB: Rambling, Incoherent Thoughts on Xander Bogaerts and the Red Sox Offseason

Jake T. O'Donnell
9 min readDec 8, 2022

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Billie Weiss/Boston Red Sox/Getty Images

I woke up much earlier than normal this morning, somehow I knew something had happened overnight. Lo and behold, my phone had dozens of notifications, all for a piece of information I was stunned to see — after a day of positive news tidbits about his possible return to the Boston Red Sox, Xander Bogaerts signed overnight with the San Diego Padres for a whopping 11-year, $280M contract.

We know from Alex Speier that the best Red Sox offer was six years and $160M, a higher AAV than what he ultimately took from the Padres. We also know from Pete Abraham that several other teams offered $200M+ to Bogaerts.

So, with that, here are some rambling, incoherent thoughts about this and what it means in the bigger context of the Red Sox offseason.

Good for Bogaerts. This, the first offseason of a new CBA, has been a great time to be a free agent across the board and that’s no different for Bogaerts. If anyone deserves to get a huge free agent contract, it’s him. He’s a great human being and it’s been fun to watch him for the last nine years here in Boston. It hurts to see him leave.

I went in depth in this piece about Bogaerts, what he’s meant to Boston since he arrived, but also the realities of where he’s currently at as a player and what committing to him would mean going forward. It’s an old adage when it comes to free agency, but you have to keep in mind that you’re paying for what the player is going to be over the course of a deal, not who they’ve been.

It’s been said over and over since the news broke, but the Red Sox absolutely should not have matched an 11-year contract for someone like Bogaerts who is certain to age poorly as a player. I’ll be stunned if he actually plays for the entirety of the deal.

Giving a huge contract to an actual free agent in their 30s would have been extremely out-of-character for the Red Sox under John Henry, they’ve only done it once: David Price. We all know how that turned out.

As I said, I feel great for Bogaerts that he got that contract, just as I feel great for any player who gets significantly paid in a sport where owners make billions. But I feel just as great that the contract is going to be with someone else besides Boston.

What did Bogaerts really want? I’ve heard over and over and over, since probably sometime in 2021, that all Bogaerts wanted was “what’s fair.” What I think we may be seeing now is that his, and his agent Scott Boras’, definition of “what’s fair” is not really what fans and media believe it to be.

It needs to be stated that Bogaerts already agreed in 2019 to forgo free agency and accept a bit less money than he could have gotten on the open market. This was against the wishes of his agent, who generally takes all his players to free agency and goes for the top dollar.

I remain extremely dubious on the idea Bogaerts was not going to exercise his right to free agency this offseason and explore all his options, regardless of any reasonable pre-opt-out offer from the Red Sox.

We can all agree that the Red Sox extension offer that tacked a year and another $10M on top of his existing pre-opt-out deal was a huge mistake, one I still can’t believe anyone thought was a good idea. That was likely a big contributing factor to him being kind of moody during the season.

But what’s clear is Bogaerts was expecting the Red Sox to treat him like he was an actual free agent in extension talks, which is rarely how things actually go. There was reporting in pre-season that what Bogaerts wanted was in line with what other free agents had made, in the eight-year, $240M range.

Would Bogaerts have actually accepted something close to what the Red Sox reportedly offered this week (the aforementioned six-year, $160M offer) if they made that offer before the 2022 season? Only he can answer that, but based on all available evidence, I’m very skeptical he would have done so.

[UPDATE, THURSDAY PM: Earlier today, Speier and Abraham co-bylined a piece in the Globe that had quite a bit of inside info on the contract negotiations over the last year between the Red Sox and Bogaerts. This tidbit got some attention online:

Bogaerts, a source suggested, would have been open to a new deal that was in the range of what Story received. The five-year, $151 million agreement that Astros star Jose Altuve landed in his extension several years earlier likewise represented a framework that Bogaerts would have welcomed.

Leaving aside for the moment that six years and $140M is a lot different from five years and $151M, this new piece of info doesn’t totally comport with what ESPN reported in April about what Bogaerts actually asked for from the Red Sox at that time:

Boston offered Bogaerts an extension during the offseason, but the 29-year-old turned down the offer. According to team sources, Bogaerts asked for a contract that paid him in line with the game’s highest-paid shortstops: Carlos Correa (who makes $35.1 million with the Minnesota Twins), Francisco Lindor (who makes $34.1 million with the New York Mets) and Corey Seager (who makes $33 million with the Texas Rangers).

So, piecing this together, it appears the Sox made the lowball offer, and Boras countered with deals in the $34M AAV range. The Sox said no. It’s apparent Bogaerts didn’t tell the Red Sox he would actually accept a Story/Altuve kind of deal, which makes sense as a negotiating tactic. In general, I have a hard time buying that Boras would have allowed Bogaerts to actually accept such a small deal he was willing to take, knowing he could take his client to free agency and get him a lot more, which he did. Anyway, back to what I wrote this morning.]

I’m not begrudging Bogaerts for any of this — players work their whole lives for free agency, to get to choose their destiny and maximize their earning potential. I just can’t help but feel the media and fans got played to a degree about what Bogaerts was willing to accept to stay in Boston before going to free agency.

He wanted to get paid at the top of the market, and he did. In my opinion, that’s what constituted “fair” to him.

What happens now? The Red Sox were having a pretty good day before the news broke about Bogaerts overnight. They signed Kenley Jansen, one of the best closers of his generation, to a two-year, $32M deal, and also won the bidding for superstar Japanese outfielder Masataka Yoshida on a five-year, $90M deal.

They’ve missed out on a number of free agents they reportedly wanted, including Jose Abreu, Zach Eflin, Mitch Haniger and Andrew Heaney among them. And now, they’ve struck out on their stated #1 option at SS.

It would be my hope the Red Sox would pivot to signing Carlos Correa, the clear top SS on the market, who’s two years younger than Bogaerts, is personally close with Alex Cora, and would not cost draft picks to sign. The fact they were willing to go to six years with Bogaerts would indicate a willingness to possibly go to eight with Correa.

But like Bogaerts, Correa is represented by Boras, and after opting out of his contract with the Twins he has tons of suitors. Reportedly the Giants are heavily in on Correa after losing out on Aaron Judge. The Cubs, Cardinals, Orioles and a reunion with the Twins are also possibilities.

After Bogaerts and Trea Turner both got 11-year contracts, you’d assume Boras wants to find at least that many years on a deal for Correa and I have a feeling at least one of the teams I mentioned above would oblige. I’m not sure I see the Red Sox being that team.

Dansby Swanson is also out there, and while he provides elite defense, I don’t know if I see his overall profile as a real fit here, plus he got the qualifying offer. The Red Sox have reportedly shown some interest, though.

If not one of those guys, or a trade option that’s not clear at the moment, the Red Sox could go with a stopgap at SS and try to fortify other areas. Elvis Andrus is still solid defensively. Jose Iglesias has a lot of history here and could hold his own. They could consider signing a 2B like Jean Segura, Adam Frazier, Josh Harrison or Brandon Drury, or trading for one like Jake Cronenworth, and slide Trevor Story to SS.

Internally, they could go with some combination of Story, Kiké Hernandez, Christian Arroyo and the newly-acquired Hoy Park to fill the 2B/SS spots without going outside the organization for help. But, in order to field a competitive team, the Sox will have to do a lot more in other spots if that’s the plan. They still need a DH and possibly another OF, and this approach could lead them back into trying to upgrade at catcher too.

I’ve been wondering even before this if the Sox will consider leaning into more of a run prevention model. We’ve already seen them load up in the bullpen with Jansen, Chris Martin and Joely Rodriguez. We know they’ve said over and over they intend to land another starter. A Nathan Eovaldi return is on the table, and there’s been significant interest in signing Kodai Senga. They could explore trades here too.

The best starter still out on the free agent market is Carlos Rodon, another Boras client. Would the Sox consider taking a run at him now? While signing Rodon would cost two draft picks, they’re getting one back now for letting Bogaerts walk.

On the run prevention idea, Yoshida is a superb hitter but not much of an OF defender. They could try to acquire a stalwart defender to take over RF and possibly move Alex Verdugo in the process. A trade for Max Kepler or Daulton Varsho would help in this area.

A word on Rafael Devers. One of the things over the last year that has really annoyed me about Red Sox discourse (and believe me, there have been a lot of them) is the idea that Bogaerts’ free agency was somehow directly tied to whether Rafael Devers would agree to a long-term extension before he hits free agency after the 2023 season.

People have tied themselves in knots, based purely on speculation, on the idea that Devers would not sign an extension unless Bogaerts was here too. There’s no proof of this, and overnight last night a couple of reporters downplayed that idea.

However, the Red Sox can no longer use needing to pay other free agents as an excuse to not give Devers what he wants, which is reportedly 10 years and $300M. Devers could be looking at the free agent contracts being doled out this winter and decide he wants to test those waters himself. Conversely, he’s not a SS, nor is he coming off a record-breaking HR season.

This is 100% his team now, and the Red Sox need to pay him like that. If they don’t, and they allow him to leave in free agency, that’s when it will be time to question Fenway Sports Group’s commitment to the Red Sox and whether or not their plan is to own the team over the long haul.

I know people are mad at Henry and FSG right now, but trust me when I say this: with new ownership, the grass is NOT always greener, and the current owners brought four titles to Boston in two decades.

The clock is ticking and fans have a right to be losing their patience given how everything has gone here since 2018, minus the fun playoff run of 2021. I have faith things will work out, and the Sox will be relevant again soon, but it has to actually happen.

In the interim, being a Red Sox fan will continue to be a nerve-wracking exercise.

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Jake T. O'Donnell

Writing stuff on a number of topics since about ’90 or ’91 I’d say.