Trade for Jacoby Ellsbury and Make the Yankees a Champion

The Yankees have some relative holes in their roster.  Not many, but when you want to ensure a World Series as much as possible, you want to try to cover those holes up.  The club has some uninspiring play in their infield and they have shown a desire, rather unique to the Yankees, that they would like to make Jordan Montgomery their sixth pitcher as opposed to their fifth one.  Combine that with a 2018 payroll of 162 MM and a desire to spend less than the 35 MM allotted under the luxury tax, they are in a very minor bind.  In 2019, about 20 MM will come off the board after consideration for arbitration, so it might be a long term issue to some extent.  If they truly want Manny Machado in 2018, they will need to shoulder his expected salary of 17.2 MM.  Beyond 2018, if they succeed in their rumored desire for him, then they may well need 40 MM a year.

This payroll crunch can be vastly simplified for the club if they do one thing: trade Jacoby Ellsbury.  Ellsbury has been passed by with Aaron Hicks establishing himself in centerfield.  Ellsbury, who has three years and 63 MM remaining with an additional 5 MM to buy out a fourth season, is effectively a very expensive Jarrod Dyson.  Ellsbury is a strong platoon bat from the strong side who should be sat as often as possible when a leflty appears on the mound.  His defense is still strong (though no longer exceptional) and he would immediately become the Orioles fastest player on the roster even as he enters his age 34 season.  His likely output would be in the 1 to 2 WAR range, which is a useful role playing starter.

For the Orioles, Ellsbury would help bridge a gap from an Adam Jones centerfield to, well, an Ellsbury one until his deal runs out.  Jarrod Dyson would also fit here and his expected pay around 8-12 MM a year provides one measure to show Ellsbury's break even point.  One benefit with Ellsbury over Dyson is that Ellsbury is a bit more respected in the game and it may be that a veteran like Jones would be more amiable to let another established veteran like Ellsbury take over instead of career platoon player Dyson.  But maybe not.  Anyway, there is a need and Ellsbury could fit.

Specifically, Ellsbury has 68.4 MM coming to him.  BORAS thinks his value would be worth a two year deal for a total of 19.4 MM this off season.  If his decline adheres to my projection, then that third season would have a future market value of one year and 8.3 MM.  This give a total value of 27.7 MM with a worth of -40.7 MM.  Earlier I noted that Manny Machado was worth somewhere in the neighborhood of 40-60 MM for 2018.  Let us be kind and peg his value and Elsbury inclusion to totaling 100 MM in assets for the Yankees to send back to the Orioles.

The Gleyber Torres Scenario
The jewel in the Yankees minor league crown is Gleyber Torres.  He would be the ideal prize if the Orioles would deal Machado over to the Yankees.  He is largely seen as Machado-light and is arguably the best prospect in baseball.  That gives him a value about 72 MM, a value that would only be possible if the Orioles took on Ellsbury's contract.

Why would the Yankees do it?  Torres is a great prospect, but he is not really a need.  They have suitable backup options at second, third, and short.  If Machado is the long term solution at short, then the Yankees would potentially be wasting Torres' value by pushing him around the diamond.  Dealing him out for one season (and potentially no more) of Machado would be a relatively insane thing to do for a lesser revenue club, but the Yankees position does make Torres movable.

To make up the rest of the package, you could argue that Chance Adams and Justus Sheffield would fit well.  Replacing Sheffield or Adams with Miguel Andujar could work and New York might see replacing Andujar easier than finding more starting pitching depth.  Some are very high on Sheffield, so his inclusion might be a bit more pie in the sky.  With Andujar, the Yankees could probably slide in someone like Todd Frazier.

The final deal would probably be Machado for Ellsbury, Torres, Adams, and Andujar.  It would give the Orioles four 2018 players.  It would remake half of their infield, provide a starting pitcher, and kick the can on a major issue in the outfield for a few years.

The non-Gleyber Torres Scenario
This would be a far higher quantity of players going back to the Orioles.  The Machado replacement would be Miguel Andujar, who has a value of about 20 MM.  Chance Adams and Justus Sheffield are two arms that the Orioles would love in the organization and are worth about 20 MM each.  Domingo Acevedo would be a strong target.  The righthander can raise his fastball to triple digits, but has had some injury issues in the past that might be related to overuse.  He could be a strong solution to Brad Brach leaving after 2018.  A 20 MM value on him might be a bit too much, but a 100 mph fastball holding its own somewhat at AAA as a starter is a nice item to have.  Finally, Nick Solak who is a relatively non-descript second base prospect who just seems to perform.  His tools are rather unimpressive, but he performs. That is a good piece.

This monster of a deal would be Machado for Ellsbury, Andujar, Adams, Sheffield, Acevedo, and Solak.  It would provide the Orioles with potentially five 2018 MLB pieces and Solak who would be a depth solution in case Jonathan Schoop departs at some point.

Conclusion
It would be frankly surprising to see the Orioles take on money to get a better deal.  That said, these deals are largely them handing over one player who would be paid 17.2 MM and getting back a multitude of MLB players for about 24 MM.  Spending 7 MM on three or four addition starters is a pretty cheap deal.  Keep in mind that only Gleyber Torres has a decent expected success rate.  The others are far less likely.  Also keep in mind that by taking Ellsbury off their hands, the Orioles set up the Yankees payroll to more easily reconfigure itself to make big runs at the Machado, Bryce Harper, Clayton Kershaw free agent season of 2018/2019 without difficult luxury tax challenges.

It is a tough call to make.

***Edit: One more thing to add, based on Perez' prospect outcome work and a couple things behind the scenes, we can expect the Torres package to deliver roughly one player (1.05) who average 2 WAR or better per season over his first six season from those three prospects.  In the second package, the likelihood is 0.87 players with 2 WAR or better.