MLB: Red Sox 2022–23 Offseason Primer

Jake T. O'Donnell
8 min readNov 6, 2022

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Julio Cortez | Credit: AP

The World Series is over, and the most important offseason in recent Boston Red Sox history is upon us.

I began publishing offseason outlook posts way back on Aug. 28, and in total I ended up writing eight of them. Since Chaim Bloom took over in 2019, it was clear this was going to be a critical winter that could color the next decade of what this team will look like. The Red Sox had such a lousy season in 2022 that it was impossible not to start thinking about the future so soon.

I’m going to briefly do some scene-setting, and then go through all of my previous offseason posts with some key points and updates since I published them.

The Red Sox will open the offseason with a projected $146.47M in Collective Bargaining Tax (CBT) payroll commitments for 2023, according to the accurate, expert tabulations of @RedSoxPayroll. This is about $86.5M under the first CBT threshold of $233M.

There seems to be some misunderstanding of what that $86.5M number actually means. I certainly hope $233M won’t be a de facto cap if the plan is to get back to the postseason. They went over the 2022 CBT threshold by $4.5M for a team that won 78 games, and in 2023 they can spend to $273M without anything beyond a financial penalty (going above that would result in draft pick penalties). There’s no good reason why the team should be treating that first CBT threshold as their spending limit.

Within the next few days, decisions will have to be made by both the club and players on impending options and opt-outs, and the club will have to make calls about issuing qualifying offers.

We know based on the reporting of Alex Speier that Chris Sale will opt-in to the final two years and $55M on his contract. Eric Hosmer will almost certainly also opt-in to the final three years of his deal, for which the Red Sox will only pay the MLB minimum salary. Xander Bogaerts will almost certainly opt out of the final three years and $60M of his deal.

It’s extremely unlikely the $12M mutual option for Tommy Pham’s deal will be exercised. The Red Sox hold a two-year, $26M option on James Paxton, and if that is not exercised, Paxton holds a one-year, $4M player option. Speier speculated last week that neither of the Paxton options will be exercised.

We’ll also find out which Red Sox free agents will receive one-year, $19.65M qualifying offers for 2023. If the players reject them, the Red Sox will be entitled to draft pick compensation if they sign elsewhere. The only definite qualifying offer recipient is Bogaerts, if and when he opts out. Pham, Paxton, Matt Strahm and Rich Hill will not be getting them. There has been reporting that J.D. Martinez will not get a qualifying offer, which is not surprising.

The unknown decisions are around Nathan Eovaldi and Michael Wacha. On Eovaldi, the new Adam Wainwright one-year, $17.5M contract might be a guidepost since Eovaldi had a better year (in fewer innings) than Wainwright in 2022.

I think Eovaldi gets one and Wacha doesn’t. I also suspect Eovaldi will reject the offer. Because this is such a middling free agent market for starting pitchers, Eovaldi should have multi-year offers on the table. In his free agency predictions column, Jim Bowden projected Eovaldi to get a four-year, $90M deal this winter. We’ll see if it gets to that level, but he should do a lot better than around $20M guaranteed.

The annual GM meetings start Monday in Las Vegas. Sometimes actual moves happen at these meetings, but usually it’s about getting discussions going and laying the groundwork for things that happen in the future. The Winter Meetings will start Dec. 4 in San Diego. This tends to be where lots of stuff happens.

I truly hope this winter’s hot stove will actually be hot from the get-go. The last few offseasons have been weird because of COVID-19 and the lockout last year, and teams seem to want things to drag out in hopes of waiting out the players to get the best deals.

I’d love to see the vast majority of winter business done by the end of the Winter Meetings, but I know that’s probably a pipe dream. Let’s just hope it’s not dreadfully boring until after the 1st of the year like some past offseasons.

Here’s all the stuff I wrote at the end of the season about this Red Sox winter:

Part 1: Setting the Scene, Devers Extension

I already set the scene above.

As for Rafael Devers, there was a flurry of reporting at the time of his 26th birthday on Oct. 24 that the Red Sox had visited him in the Dominican Republic and likely made a new extension offer. There has not been much reported since then other than that the sides are still fairly far apart on a deal, but negotiations continue.

I have all my fingers and toes crossed that something gets done here, but Devers has all the leverage. Here’s hoping there is enough common ground to keep Devers for a long time, and we finally get the answer to the question we’re all wondering: is Devers a Fudgie the Whale guy or a Cookie Puss guy?

Part 2: Outfielders (and Bonus on this topic as well)

In my original post on how the Red Sox should fill their hole in the outfield, I went over free agent possibilities Aaron Judge, Michael Conforto, Brandon Nimmo, Joc Pederson and Mitch Haniger. Of these, I like Conforto the best from both a realistic standpoint and a bang-for-your-buck standpoint. I’ve found myself intrigued by Haniger, as long as he doesn’t get a qualifying offer.

I mentioned several trade possibilities as well, and I believe the Red Sox are most likely to make their most significant trade acquisition this winter to address the outfield. I discussed Max Kepler, Bryan Reynolds, Ramon Laureano, Ian Happ and Cody Bellinger.

I was really into the idea of trading for Kepler, but I’m more worried now that his best year, 2019, was a fluke due to the juiced ball. Reynolds would be perfect, but won’t come cheaply.

I came up with more trade partners for an outfielder in my most recent post, and I covered possibilities with the Cardinals, Guardians and Orioles. Tyler O’Neill is my favorite potential trade target, given that St. Louis has a crowded outfield and he checks many boxes Bloom and Alex Cora have discussed wanting for next year’s team. There are injury concerns with O’Neill, to be clear.

One last thing: Chris Cotillo posted an interesting article about Alex Verdugo on Friday. Cotillo says the Red Sox were generally unhappy with Verdugo’s performance in 2022, didn’t like the fact he bulked up for the season, and took issue with his preparation methods. This has led to some speculation he could get moved this winter. I’ve typically been a pretty big Verdugo defender, and trading him would create two outfield holes instead of one. But, if another team values him, it’s definitely worth exploring what he’d return on the trade market.

Part 3: Shortstops

Yes, I do want Bogaerts back. But, many fans in Boston have allowed emotions around a fine ballplayer and a better person to get in the way of the objective truth: Bogaerts has been steadily declining at the plate since 2019 and his solid defense this year may have been a mirage caused by the now-banned shift.

Not signing Bogaerts is extremely defensible. What would be indefensible is letting him go without making a serious effort to sign another top shortstop. Trea Turner strikes me as the exact kind of guy Bloom would want. Carlos Correa has a longstanding relationship with Cora and is arguably the best bet to live up to a huge contract of any free agent this winter. I’m not as high on Dansby Swanson, but he’s in the conversation.

There will also be talk about the Padres trading Fernando Tatis, Jr. I wrote a long thing about this I might post at some point. I don’t see it for the Red Sox, or anyone else really, but it’s going to come up. Be prepared, I guess.

Part 4: Designated Hitter

As I mentioned, Martinez is likely not getting a qualifying offer and more likely than not the Red Sox will be moving on from him. The team has been clear they want more versatility and the idea of bringing back a DH-only option doesn’t fit with that.

In my view, the best option is to trade Hosmer and bring in a right-handed hitting 1B to complement Triston Casas. I don’t know if that’s how the Red Sox feel too, but in my piece I discussed José Abreu, Trey Mancini, Josh Bell, Wil Myers and Carlos Santana. Abreu is my favorite of this group, and there was some chatter last week the Sox have interest in him.

This is one area where the Sox might consider thinking outside the box, too.

Part 5: Starting Pitching (In-House Options)

I spent a good chunk here outlining a pattern: the Red Sox under Bloom have been disinclined to pay a high acquisition cost for pitching — whether in trades or free agent signings, or draft and international signing bonuses. That’s something important to keep in mind this winter.

I went over Sale, Paxton, Nick Pivetta, Brayan Bello, Kutter Crawford, Connor Seabold, Josh Winckowski, Garrett Whitlock and Tanner Houck. In order for the Red Sox to improve on what was a below-average MLB pitching staff next year, these in-house options will need to be augmented.

Part 6: Starting Pitching (Free Agents & Trades)

It’s not the greatest free agent market for starting pitching, but there are some interesting guys. I started by discussing Eovaldi and Wacha, then went into Carlos Rodon, Justin Verlander, Tyler Anderson and Mike Clevinger before briefly mentioning several other free agents. Of those guys, I most want the Red Sox to make a serious run at Verlander. I am not at all expecting interest in Jacob DeGrom.

I didn’t go too deeply on any one trade option. It’s hard to say who would actually be available, and any significant starting pitcher at the top of a rotation would be wildly expensive. I’ll reiterate: if the Red Sox make a big trade this winter, it is much more likely to be for a position player than a starting pitcher. But, I’m sure that won’t stop the speculation.

Part 7: Bullpen

The bullpen was mostly a disaster for the Red Sox in 2022 and they need a serious infusion of talent out there. Some possible RHP free agent targets include Rafael Montero, Kenley Jansen, David Robertson, Chris Martin and Adam Ottavino. I like Montero the best, despite him starting to wear down in the postseason. I don’t see a realistic pursuit of Edwin Diaz.

The Sox also may need to fill two LHP bullpen spots, and I mentioned Matt Moore, Will Smith, and Andrew Chafin (who is reportedly declining his player option in Detroit) as possibilities.

For trade targets, I went over a few guys who theoretically could be on the market, including Alexis Diaz, Scott Barlow, James Karinchak and Trevor Stephan. Short of more obvious moves, I trust Bloom to go out and find the next John Schreiber by targeting undervalued guys who could male a difference in the bullpen.

Let the action begin! I’ll check back in here as appropriate.

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Jake T. O'Donnell

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