With the firing of GM Dave Dombrowski, it is clear that the Red Sox are going to move their team into a different direction. That direction would include cutting payroll and possibly trading their biggest star, Mokie Betts, in order to do so. If the Red Sox are exploring trading Betts, the Chicago White Sox must be flirting with the idea of trading for him.
It won’t happen until they get a new GM, but the Red Sox may be exploring trading Mookie Betts. If they do explore trading him, one of the best fits might be the Chicago White Sox. There is no player that would help the White Sox more and perhaps no team that would be a better fit for baseball’s second-best player in the league.
The Red Sox will probably try to sign him to an extension first, but he likely won’t sign it, opting to become a free agent and explore his market. The Red Sox may then trade him to a suitable team, hoping to get a decent package for him before he leaves while helping the team save money.
So why would Mookie Betts go to the White Sox? For one, he is a near-perfect fit for the team. The White Sox are hoping to contend in 2020, and they’ll need to improve on their weakest position (right field) in order to do so. Betts is probably the best right fielder in the game, and getting him would likely add at least 8-10 wins to the team, given how much room for improvement they have at the position.
The Red Sox would probably want a healthy batch of prospects in return, which does make the White Sox seem like at least a feasible landing spot, given that they still have a lot of prospects they can trade. However, the Red Sox would be wrong to demand a package similar to what they traded for Chris Sale. For one, Betts only has one year of control, whereas Sale had three years and was pretty cheap considering the production he provided.
Betts is probably a more valuable commodity, but he has only one year left of control and will demand a hefty salary going forward, so he doesn’t merit the kind of return that Sale got the White Sox in the trade. Given this, the White Sox would be able to make the deal happen. They may have to get creative to do so.
If they don’t want to give up prospects, the White Sox could try taking on a bad contract like that of Rusney Castillo. This could help Boston cut costs, and the White Sox have the payroll flexibility to take on Castillo’s contract and employ him as a fourth outfielder – would he really be much worse than several of the options the White Sox have tried in the outfield this year? Catillo has an 82 OPS+ for his career, which isn’t worse than what Adam Engel and Leury Garcia have done this season.
With the Castillo possible addition aside, it is hard to see who the White Sox would give up that would get the deal to go through. Moving Michael Kopech back to his original team would certainly be creative and interesting, but the White Sox have invested too much in Kopech to go shopping him around at this point. Also, neither team would do a Kopech trade until seeing how he performs in the big leagues after recovering from Tommy John surgery in 2019. And most importantly, the White Sox badly need the starting pitching, so it’s hard to see him being included.
Nick Madrigal is someone who could get the trade done as well, but then there goes the White Sox future at the keystone position. The White Sox could sign Anthony Rendon and make Yoan Moncada shift back to second base but do you really expect the White Sox to sign Mookie Betts to a mega-contract and get Rendon signed on top of that? Not likely, given their history of spending.
The White Sox might just trade for one year of Mookie Betts and see if he can get them to the playoffs, but would it really be worth it if they aren’t going to extend him? They should try to trade for him and then use that experience to convince them to sign with them when he becomes a free agent, similar to what they tried to do with Manny Machado in 2018.
The most likely trade scenario that could go through would be a packaged deal of Betts and Castillo going to the White Sox for a decent crop of second-tier prospects who are outside of the top-four prospects in the White Sox system but good enough to get the deal done. Let’s hope they can pull through with this one.