How the Red Sox Should Finish Their Offseason

Robbie Hyde hosts his own MLB-focused YouTube channel.


Since losing in the 2021 ALCS, the Red Sox have endured the misery of back-to-back last place finishes, dismissing Chaim Bloom from his role as Chief Baseball Officer, and attempting to right the course by bringing in former Red Sox reliever Craig Breslow to lead the way.

Like many others, Breslow came in and knew immediately that expectations would be through the roof, especially with the ill-fated “full-throttle” comments from chairman Tom Werner early in the offseason. 

With the starting pitching in shambles last season, as well as needing a right-handed hitter to replace the productive bat of Justin Turner, Boston fans thought this could be one of the most exciting offseasons in quite some time. They were dreaming of the possibility of Yoshinobu Yamamoto at Fenway Park for years to come, or Corbin Burnes dueling with Gerrit Cole and the Yankees, or maybe even a pitcher in a different color pair of socks in Dylan Cease leading the rotation. There was also the idea of Jorge Soler hitting over 800 home runs onto Landsdowne St.

Unfortunately, none of that has happened. Instead, there has been more of the opposite, as the Red Sox are looking to spend even less than last season – President Sam Kennedy said he sees the payroll being lower than the reported $225M in 2023. 


So what have they done?

For the most part (so far at least), Sox fans have seen less flashy but more logistically productive moves, mostly on the trade front, along with some additions in the front office, and hiring Andrew Bailey as the pitching coach. 


Early offseason trades

With the Red Sox needing to shed some salary, Breslow made a bold move by trading away a bad contract in 2018 World Series hero Chris Sale to the Braves, which brought in a much-needed second baseman in Vaughn Grissom, who was blocked in the Braves system. 

They also traded Alex Verdugo in a rare in-division deal to the rival Yankees, which did bring in some needed organizational pitching depth in Richard Fitts and Greg Weissert. 

To replace Verdugo, they acquired Tyler O’Neill, who was in much need of a change of scenery after a couple injury-riddled seasons in St. Louis. 

Breslow also made a low-key move with the Mariners, bringing in young reliever Isaiah Campbell, who has shown a lot of promise as a possible high upside arm for the bullpen. 

More recently, he traded middle reliever John Schreiber to the Royals for a young arm with upside in David Sandlin, and also signed Liam Hendriks to a 2-year deal with incentives. While he probably won’t see much action in 2024 if any, he should be a reliable bullpen piece for them in 2025. 


… and one significant free agent signing

It wasn’t just trades, though, as there was a free agent addition in Lucas Giolito, who had a very rough second half after a good first half in 2023. While he may not be World Series champion Jordan Montgomery or Cy Young winner Blake Snell, he does have a good track record and has shown to be an innings-eater in his career, something that should benefit the Sox in 2024 after their starting pitching finished 27th in innings pitched. 

All in all, it’s fair to say this offseason has been more on the lackluster side. While there’s still much to be desired with this roster and with plenty of free agents and trade candidates still out there, the Sox have time to turn this offseason around.

Where to go next?


Address the rotation: Sign Jordan Montgomery

Most of all, the Sox need to address the starting pitching even after the addition of Giolito. Their current projected staff of Brayan Bello, Giolito, Nick Pivetta, Kutter Crawford, and Tanner Houck is only projected to be 18th in the Major Leagues at this moment, according to FanGraphs. 

One obvious way to correct this is to sign Jordan Montgomery. The rotation lacks a lefty, and could use another consistent and durable pitcher to give them innings. He also spent his offseason in Boston while his wife has been doing her residency for dermatology at Harvard, he shouldn’t cost as much as Blake Snell, and they won’t have to give up draft-pick compensation due to the lack of a qualifying offer attached to him. 

It was reported Montgomery’s agent Scott Boras is looking for a Carlos Rodon type of contract (6 years, $162M), and is trying to hold out as long as possible. 

Unfortunately for Montgomery, other teams don’t seem to be lining up for him. His previous team, the Rangers are having TV Money issues; the Phillies are working on an extension for Zack Wheeler; the Cubs seem set with their rotation after adding Shota Imanaga; the Angels appear to be unsure if they’ll spend money, and are reportedly more connected to Blake Snell; and the Astros, who have expressed a desire to add SP, already have a franchise-record payroll after adding Josh Hader. 

With pitchers and catchers already reporting, the contract-length expectations are going to have to come down at some point, which would fall right into the Sox’ wheelhouse. For pitchers, they don't seem to want to go past three years, but reports suggest Montgomery would be inclined to go to a team with a better chance of contending on a short-term deal if he doesn’t get the years he’s looking for. 

To ensure he comes to Boston, let's do a 4-year deal. According to BTV’s Future Free Agent Tool, it would take $111.6M over 4 years to get it done. Let's do a round number of $110M over 4 years, so $27.5M per year. 


Time to clear more salary: Trade Kenley Jansen

With the Sox seemingly having a desire to lower their payroll this season from last season, it would behoove them to make some space. As of right now, the current Luxury Tax payroll sits at $202M according to FanGraphs. 

One contract taking up space is Kenley Jansen’s, who’s owed $16M for 2024.

There are a couple ways to clear Jansen from the payroll. You could simply just trade him by himself somewhere with teams like the Dodgers, Padres, Rangers, and Royals having expressed interest this offseason. 


Proposed trades:

Padres/Red Sox:

  • Padres get: RP Kenley Jansen (-$2.1M), Cash ($4M)
  • Red Sox get: SP Victor Lizarraga ($2.3)

Dodgers/Red Sox:

  • Dodgers get: RP Kenley Jansen (-$2.1M), Cash ($4M)
  • Red Sox get: SP Justin Wrobleski ($2.3M)

Phillies/Red Sox:

  • Phillies get: RP Kenley Jansen (-$2.1M), Cash ($4M)
  • Red Sox get: Griff McGarry ($2.0M)

However, reports say the Sox don’t want to eat any of his salary, and with Jansen’s contract currently under water (-$2.1M), this might not be desirable to other teams especially if the Sox want something in return. 


Trade Jansen along with a more valuable piece

One possibility: pair him with another player who’s also been coming up in trade rumors as well, and that's speedster Jarren Duran. The Padres currently have only one capable everyday outfielder on their roster in Fernando Tatis Jr. They could also use a bonafide closer even after signing a couple relievers from overseas in Yuki Matsui and Woo-Suk Go, along with lefty Wandy Peralta. Padres GM A.J. Preller and Senior Advisor Logan White both also have connections to Jansen from their time with the Dodgers.  

While the Padres have had some reported issues with payroll this offseason, they’re still far under the first CBT threshold at $215M, so they should be able to absorb Jansen’s contract for one season, especially if it means they get to add a cost-controlled outfielder in Duran, who's coming off a breakout season. 

While the Sox are looking for cost-controlled starting pitching, they could also be interested in adding one of the Padres higher-rated pitching prospects, Robby Snelling or Dylan Lesko. With Snelling a bit closer and Lesko recently coming back from Tommy John surgery, it’s plausible Boston would want Snelling instead.

Proposed trade: Padres/Red Sox

  • Padres get: OF Jarren Duran ($34M), RP Kenley Jansen (-$2.1M)
  • Red Sox get: SP Robby Snelling ($25.7M)

The BTV simulator grades this as a Minor Overpay. However, this trade itself feels a bit flat considering the Red Sox are giving up two MLB-ready players for someone who hasn’t pitched one inning at the MLB level.

Or we can explore three-way deals like this one:


Let’s get complicated, option 1

While the Padres have been connected with Duran, they’ve also been connected to another OF, Sal Frelick, the Brewers’ No. 15 pick from the 2021 MLB Draft. Let's make this a bit more interesting, and perhaps the Brewers could get in on a 3-way trade with the Red Sox and Padres.

Proposed trade: Padres/Red Sox/Brewers

  • Padres get: OF Sal Frelick ($35.4M), RP Kenley Jansen (-$2.1M)
  • Red Sox get: SP Robby Snelling ($25.4M)
  • Brewers get: UTIL Jake Cronenworth (-20.4), 2B Nick Yorke ($13.1M), OF Samuel Zavala ($11M), RP Josh Winckowski ($9.1M), $16M Cash

In this blockbuster, the Padres still get a young cost-controlled OF with high upside in Frelick along with a closer in Jansen. The Red Sox would be getting a SP for the future in Snelling while also being able to keep Duran as their leadoff hitter, and the Brewers would be getting a mix of MLB talent and minor leaguers, a type of trade up their alley that helps them stay competitive. 

The most notable player heading to the Brewers would be UTIL Jake Cronenworth, who has fallen off a bit after signing a 7-year, $80M extension with San Diego that starts in 2024. The Padres would be paying $16M of his $80M to get out of the contract, and with Frelick heading to San Diego, this would mean Yelich can stay in the OF. 

As for the infield, Rhys Hoskins can spend more time at DH and Cronenworth can man 1B while also having versatility to play other positions. They would also receive another MLB piece in LRP Josh Winckowski, who could be used either as a starter or reliever, and position-player prospects Nick Yorke and Samuel Zavala. 

The BTV simulator approves this as a Minor Overpay.


Let’s get complicated, option 2

If the Sox were more interested in getting a starting pitcher who can help them more in the short term instead of having to wait for Snelling, the Marlins are a possible option. They’ve been rumored to have their starting pitchers on the trade block. They’re in an awkward spot right now, where they have a decent team, but without Sandy Alcantara this season, it could be an uphill battle to compete, especially with all of the talented teams in the NL making upgrades. 

One big piece the Marlins have that could be of interest to the Sox is Jesus Luzardo, who's coming off a fantastic season in Miami and would give Boston a cheaper, cost-controlled SP for three seasons. Trading Luzardo could be a way for Miami to maximize his value while bringing in pieces that can help them both now and for the future. In this blockbuster deal, the Red Sox, Padres, and Marlins would all benefit. 

Proposed trade: Padres/Red Sox/Marlins

  • Padres get: OF Jarren Duran ($34M), RP Kenley Jansen (-$2.1M)
  • Red Sox get: SP Jesus Luzardo ($65.4M)
  • Marlins get: SP Robby Snelling ($25.4M), 2B Nick Yorke ($13.1M), OF Samuel Zavala ($11M), IF Enmanuel Valdez ($8.1M), SP Wikelman Gonzalez ($5.1M)

In this deal, the Padres get their OF and closer, the Red Sox get an MLB-ready cost controlled SP in Luzardo, and the Marlins receive a package that includes a top 50 MLB prospect in Snelling and another pitching prospect for their system in Gonzalez, the Red Sox’ top pitching prospect. They also get a few promising bats in Zavala, Yorke, and Valdez.

The BTV simulator grades this as a Minor Overpay, but if the Red Sox were to pay at least $1.5M of Jansen’s salary, this would be approved as a Fair Trade. 


A simpler Luzardo trade

Another option is for the Sox to deal directly with the Marlins on a similar package:

Proposed trade: Red Sox/Marlins

  • Red Sox Receive: SP Jesus Luzardo ($65.4M)
  • Marlins Receive: OF Jarren Duran ($34.0M), 2B Nick Yorke ($13.3M), IF Enmanuel Valdez ($8.1M), LRP Josh Winckowski ($9.1M)

In this deal, the Red Sox get a sorely needed cost-controlled young arm, while the Marlins get an upgrade for their offense, along with an MLB-ready cost-controlled infielder in Valdez, a cost-controlled young arm in Winckowski who can either start or go into the bullpen, and a bat for the future in Yorke.

No matter what deal happens, if the Red Sox can clear Jansen’s $16M salary while even paying some of it, this would reduce their luxury tax payroll to $190M if they threw in $4M, giving them much more payroll flexibility to add Montgomery. 

Overall, if the Red Sox signed Montgomery and traded for Luzardo, their luxury tax payroll would be right around $220M. Without Luzardo, they would be around $217.5M. 


One more bat

If Duran were to head to the Padres or Marlins, the Red Sox would most likely let Ceddanne Rafaela run with the job in CF. While there are concerns with his plate discipline, he’s a tremendous center fielder that will be able to hold it down out there. 

This would leave the Red Sox with O’Neill, Wilyer Abreu, and Rob Refsnyder as the other outfielders. There's also Masataka Yoshida, but after a poor defensive season in LF, manager Alex Cora has said he will see time mostly at DH moving forward. 

With O’Neill being more injury-prone, along with Rafaela and Abreu only just beginning their MLB careers, it could be beneficial for the Red Sox to add a veteran outfielder to the mix. There are some options, including Adam Duvall or Tommy Pham. Or, they could pivot to Garrett Cooper, a right-handed bat who could see time vs LHP and/or on days Casas/Yoshida need some rest. According to BTV’s Player Value Timeline, this is what it would cost for these players on 1-year deals:

  • Adam Duvall: $5.3M
  • Tommy Pham: $7.6M
  • Garrett Cooper: $3.4M


How would all that look?

Signing Montgomery, and perhaps trading for Luzardo or getting a top pitching prospect in Snelling, while bringing in a RHH to help out in the short term would be a solid finishing touch on a lackluster offseason, especially given the reported budget constraints. This could help bridge the gap over the next few seasons while waiting for the next core of young players to come up, and would very much keep them competitive.


About the Author


Henry will trade Jansen + Martin to cut salary. Then Henry makes endless announcements about Jordan Montgomery, and Henry claims poverty to do nothing. The Red Sox trade all the veterans at the trade deadline to clear payroll. Henry next promises to go full throttled naming Kaleb Ort their opening day starter.


Outside looking in, it seems as though the Red Sox are trying to rebuild while holding on to a roughly 80-85 win potential. That’s how the Rays like to “rebuild” but of course at much lower payroll figures. Personally, I’d be surprised to see the Red Sox do anything to improve their 2024 team at this point. It’s weird, but ownership seems to be prioritizing cash flow over wins this year.