Examining hypothetical Red Sox trade scenarios

The Red Sox are set to make a big trade this offseason. Craig Breslow has made his desire clear and the club is well placed to do plenty of deals.

But if and when a deal does happen, what might it actually look like?

The Red Sox have several goals they can achieve through trade. They could trade for an elite starting pitcher. They could address one or more other roster deficiencies. They could clear a logjam of position players that makes it easier to improve the club through free agency. Or they could do something completely unexpected.

Of course, it’s impossible to know for sure what kind of trade package another club would find acceptable – everyone has their own priorities and valuations – but we can make an educated guess. So here are a few hypothetical deals that would allow the Red Sox to achieve each of the goals listed above.

Crochet blockbuster

Red Sox receive: LHP Garrett Crochet. White Sox receive: RF Wilyer Abreu, RHP Kutter Crawford, INF Chase Meidroth, OF Jhostynxon Garcia

Word is that the White Sox are looking for a collection of position players in exchange for their 25-year-old star player, but considering how ugly things got last season, they need not only prospects but also up-and-coming young players, This can quickly have an impact on the major league club. Luckily, the Red Sox have plenty of guys who fit that profile.

Abreu just won a Gold Glove as a rookie and could immediately become one of Chicago’s top three position players. Crawford pitched just 183.2 innings and was able to slot right into Crochet’s old rotation spot. Both have proven their MLB track record and have four-plus years of team control remaining, and Meidroth (Boston’s No. 11 prospect according to MLB Pipeline) had a great season in Triple-A and could be in Chicago’s starting lineup right away be included in the opening list or utility role. Garcia may not be as MLB-ready as the others, but he is one of Boston’s fastest-growing talents and projects and exactly the type of mid-range threat Chicago desperately needs.

Would Chicago bite? If they did, the Red Sox would secure an ace without having to give up any of their Big Four prospects. That would be a huge win for the franchise.

Two birds with one stone

Red Sox receive: 3B Nolan Arenado, RHP Ryan Helsley. Cardinals receive: C Kyle Teel

The Cardinals have signaled their intention to rebuild, and there have been rumors recently that Arenado, a 10-time Gold Glove third baseman, could be on the trading block. Sean McAdam of MassLive also recently reported that Arenado could be an option for Boston if the organization decides to move Rafael Devers from third base.

Let’s assume all of this happens and the Red Sox pursue Arenado. He would be an interesting addition on his own, but if the Cardinals are serious about rebuilding, the Red Sox should aim higher and try to acquire Ryan Helsley as well.

Helsley is one of the best closers in baseball and led the MLB with 49 saves last season. He would provide a huge boost to Boston’s bullpen, and Arenado would provide the right-handed bat the Red Sox have been looking for while also being a huge improvement on defense.

Boston could probably do a lot to make that happen by simply taking on a significant portion of the $74 million Arenado is owed over the next three years, but including Helsley would also require including at least one valuable prospect . Given St. Louis’ struggles at catcher since the retirement of Yadier Molina, the Cardinals would likely push for top catching candidate Teel to be the primary return, as his presence would provide St. Louis with a way out to move up Willson Contreras to move first base.

If the Red Sox weren’t willing to part with Teel, they could also offer the Cardinals a selection of about four other prospects. Maybe a deal with teenage shortstop Franklin Arias? Or right-hander Richard Fitts if he prefers to pitch?

Unload Yoshida

Red Sox receive: LHP David Peterson. Mets receive: OF Jarren Duran, DH Masataka Yoshida, cash

Masataka Yoshida is no longer a good fit on the Red Sox roster, but he might also be the hardest player in the organization to trade. His contract runs for three years and is worth $54 million. He is coming off an injury in 2024 and will spend the offseason recovering from shoulder surgery.

These factors will complicate any trade discussion, but if Boston wants to free up its designated hitter spot, there is a way to do it.

In 2012, the Red Sox parted ways with the albatross contracts of Carl Crawford and Josh Beckett by including them with Adrian Gonzalez in a blockbuster deal with the Dodgers. Boston could follow a similar plan today by finding a deep-pocketed buyer and releasing an attractive headliner. Duran would be a logical choice in this case, as the Red Sox could either sign a backup outfielder in free agency or promote top prospect Roman Anthony.

Given the Mets’ bottomless resources, they would be a logical trade partner. Duran would give their lineup an immediate boost and with JD Martinez likely out, Yoshida could step in as New York’s new DH. Boston would likely seek pitching in return, and David Peterson is coming off a career year in which he posted a 2.90 ERA and went at least six innings in eight of his last 11 starts starting in August.

Swing for the fences

Red Sox received: OF Fernando Tatis Jr., cash. Padres receive: OF Jarren Duran, RHP David Sandlin

Why should San Diego even consider this? Tatis is owed about $277 million over the remaining ten years of his contract, which is a lot of money for an organization that also made massive commitments to Manny Machado and Xander Bogaerts over the next decade. The Padres have amassed huge payroll under late owner Peter Seidler, but if the organization isn’t willing to continue doing so without him, it’s not crazy to imagine San Diego making some sort of move.

With Duran, the Padres would be getting a talented outfielder who just had one of the best all-around seasons in the major leagues, but who also offers four years of team control at a comparatively affordable price. Perhaps there would be debate about how much of Tatis’ salary Boston would take on or whether the Red Sox would need to bring in a pitching contender, but this deal would allow San Diego to maintain its status as a contender while freeing up resources in the long run. If not Duran, perhaps there is a version of this Triston Casas trade instead.

Whatever the case, a deal like this probably won’t happen, but if the Red Sox were to move on from Juan Soto, Tatis would be a real Plan B.