Let’s make a deal: Examining hypothetical Red Sox trade scenarios

The Red Sox are going to swing a big trade this offseason. Craig Breslow has plainly stated his desire to do so and the club is well positioned to pull off any number of deals.

But if and when a trade comes together, what might it actually look like?

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

Obviously it’s impossible to know for sure what kind of trade package another club would find acceptable — everyone has their own priorities and evaluations — but we can make an educated guess. So here are a couple of hypothetical deals that would allow the Red Sox to accomplish 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

The White Sox are said to be looking for a collection of position players in exchange for their 25-year-old ace, but considering how ugly things got last season, they don’t just need prospects but up-and-coming young players who can quickly impact the big league club. Fortunately, 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 just threw 183.2 innings and could slot right into Crochet’s old rotation spot. They both have proven MLB track records and four-plus years of team control remaining, and Meidroth (Boston’s No. 11 prospect per MLB Pipeline) enjoyed a terrific season at Triple-A and could slot right onto Chicago’s Opening Day roster in either a starting or utility role. Garcia may not quite be as MLB ready as the others, but he’s one of Boston’s fastest rising prospects and projects as the kind of middle-of-the-order threat Chicago desperately needs.

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

Two birds, 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 lately there’s been chatter that Arenado, a 10-time Gold Glove third baseman, could on the trade block. MassLive’s Sean McAdam also recently reported Arenado could be an option for Boston if the organization decides to move Rafael Devers off third base.

Let’s say all of that comes to pass and the Red Sox do pursue Arenado. He’d be an interesting addition on his own, but if the Cardinals are serious about rebuilding, the Red Sox should aim higher and try to get Ryan Helsley too.

Helsley is one of the best closers in baseball and led MLB with 49 saves last season. He’d provide a massive boost to Boston’s bullpen, and Arenado would provide the right-handed bat the Red Sox have sought while also representing an enormous upgrade defensively.

Boston could probably go a long way towards making this happen simply by taking on a significant portion of the $74 million owed to Arenado over the next three years, but if Helsley were included they’d need to toss in at least one valuable prospect too. Given St. Louis’ issues at catcher since Yadier Molina’s retirement, the Cardinals would likely push for top catching prospect Teel as the primary return, as his presence would provide an escape hatch for St. Louis to move Willson Contreras to first base.

If the Red Sox weren’t willing to part with Teel, they could also offer the Cardinals their pick of four or so other prospects. Maybe a deal headlined by teenage shortstop Franklin Arias? Or right-hander Richard Fitts if they’d prefer pitching?

Unload Yoshida

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

Masataka Yoshida isn’t a good fit for the Red Sox roster anymore, but he might also be the most difficult player in the organization to trade. He has three years, $54 million remaining on his contract, and he’s coming off an injury plagued 2024 and will spend the offseason recovering from shoulder surgery.

Those factors will complicate any trade discussions, but if Boston wants to move on to free up its designated hitter spot, there is one way they could do it.

In 2012, the Red Sox unloaded Carl Crawford and Josh Beckett’s albatross contracts by packaging them with Adrian Gonzalez in a blockbuster deal with the Dodgers. Boston could follow a similar blueprint today by finding a deep-pocketed taker and dangling an attractive piece as a headliner. Duran would be a logical choice in this case, as the Red Sox could either sign a replacement outfielder in free agency or elevate top prospect Roman Anthony.

Given the Mets’ bottomless resources, they’d be a logical trade partner. Duran would provide an immediate boost to their lineup and with J.D. Martinez likely on his way out Yoshida could slot in as New York’s new DH. Boston would likely seek pitching in exchange, and David Peterson is coming off a career year in which he posted a 2.90 ERA while going at least six innings in eight of his last 11 starts from August onwards.

Swing for the fences

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

Why would San Diego even consider this? Tatis is owed approximately $277 million over the remaining 10 years of his contract, which is a lot of money for an organization that’s also made massive commitments to Manny Machado and Xander Bogaerts over the next decade. The Padres ran up huge payrolls 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 kind of move.

In Duran the Padres would get a talented outfielder who just put together one of the best all-around seasons in the big leagues, but who also offers four years of team control at a comparatively affordable rate. Maybe there’d be discussion over how much of Tatis’ salary Boston would take on or if the Red Sox would need to toss in a pitching prospect, but this deal would allow San Diego to maintain its status as a contender while freeing up resources over the long haul. If not Duran, perhaps there’s a version of this trade with Triston Casas instead.

Either way, a deal like this probably won’t happen, but if the Red Sox were to strike out on Juan Soto, Tatis would be one heck of a Plan B.

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