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Why the White Sox make sense as a J.A. Happ landing spot

The Yankees and White Sox could help each other improve.

Colorado Rockies v New York Yankees Photo by Mike Stobe/Getty Images

This offseason’s hot stove is burning brighter than in recent years. Catchers and relievers led the way, now starting pitchers are beginning to follow as well. For baseball fans it’s entertaining to see an active offseason; we observe next year taking shape and realize more teams are attempting to return into contention, like the White Sox, San Diego Padres, Cincinnati Reds, and Texas Rangers.

The Yankees’ burner may seem at a simmer, but they just met with top pitchers Gerrit Cole and Stephen Strasburg. A full 40-man roster and lack of financial flexibility are two areas in need of addressing if they were to sign either, and there could be one way to do both. By swinging a trade, the Yankees can make space for free-agent signings and ship away a considerable sum of payroll.

With strengthening of the starting rotation being the top offseason priority, more specifically a top of the rotation arm, a back-end starter like J.A. Happ has become expendable. First, his sub-par performance could be duplicated or improved on by a group of young arms in Jordan Montgomery, Deivi Garcia, or Michael King. Secondly, his $17 million salary could block the Yankees from resigning Brett Gardner, Dellin Betances, or other established veterans.

Finding a trade partner for Happ requires a few things: a team that can afford his contact, is in need of starting pitching, and is looking for prospects. The Yankees would also need to be willing to offload a young player as an incentive for the trade partner to add Happ’s contract.

One team currently in contention that is in desperate need of starting pitching looks to be the Chicago White Sox. Lucas Giolito stands out as their only reliable starter heading into 2020 after a season, where he finished tied for sixth place in AL Cy Young voting. They do have Reynaldo Lopez with upside who came over with Giolito in the Adam Eaton trade, but he has yet to put it together.

Further down the road, Michael Kopech and Carlos Rodon both will be returning from Tommy John surgery, hoping to make an impact on the White Sox rebuild. Until then, adding a veteran starting pitcher like Happ could be in their best interest.

On the other side of the ball, you can count the amount of productive hitters the White Sox have on one hand: Yasmani Grandal, Yoan Moncada, Jose Abreu, Tim Anderson, and Eloy Jimenez. A couple of prospects in Luis Robert and Nick Madrigal are coming through the pipeline, but they would still need to plug a few more holes in their lineup and add depth. Acquiring controllable offensive pieces through trade could help fortify a lineup, giving them effectively a four-year window of contention.

Once the White Sox signed Grandal and extended Jose Abreu, their current estimated luxury tax payroll is about $111 million. They clearly have the money to spend as it was reported that Zack Wheller left more money on the table in Chicago, choosing instead to sign with the Philadelphia Phillies. The White Sox organization might have not been planning to spend their money on Happ, but if the Yankees add the talent or prospects needed to justify the $17 million owed to him, it could be worth entertaining.

Estevan Florial fits their window of contention as a prospect. Mike Ford should be considered as well after raising his trade value this season, noting the Yankees have plenty of corner infield depth. Thairo Estrada and Tyler Wade currently have lower trade value but could be lower ends of a package to seal the deal. The Yankees don’t have young starting pitchers as proven as their hitters, but they could offer arms with plenty of upside, such as Michael King, Nick Nelson, and Albert Abreu.

When the Yankees traded away Chase Headley and Bryan Mitchell to the San Diego Padres for Jabari Blash, in a similar deal to unload $13 million, only one club got what they needed. Considering the White Sox would be taking on more money and adding a 37-year-old starting pitcher who had a rough season, they will be looking for more than just a Mitchell.

Furthermore, if the White Sox are looking to add pieces that would help put them into contention next season like Ford, the Yankees wouldn’t ask for a Jabari Blash. The White Sox might need to consider trading one of their legitimate prospects.

Plenty of pieces are matching up for a deal to be made between these two teams. The White Sox would be adding a much needed veteran pitcher into their rotation, while also adding hitters or pitchers they can control as they hope to take over in the AL Central. Yankees would be creating space to acquire players needed to solidify their depth and making room on the 40-man roster. Brian Cashman has done it before; it’s time to do it once again.