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Trading Jacoby Ellsbury to the Giants doesn’t make a lot of sense for the Yankees

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This rumor features the Yankees trading a bad contract for an even worse one.

American League Wild Card Game - Minnesota Twins v New York Yankees Photo by Elsa/Getty Images

Let’s pretend that Brian Cashman spends his free time collecting antiques and oddities. Busy men need hobbies, right? Perhaps his involves traveling the globe, scouting bazaars and storefronts for items to keep in his office.

Now imagine if one day Cashman encounters a man who offers him an ornament that would guarantee to put visitors on edge. Talk about great leverage in business negotiations. It gets even better though, as the item grants three wishes to its owner. A completed transaction: Cashman acquired one monkey’s paw in exchange for cash considerations.

Armed with three wishes, one could imagine that Cashman would undo the Yankees’ biggest blunder in recent memory. So long Jacoby Ellsbury, and take your remaining two years and approximately $42 million with you!

And just like that, Ellsbury would be off the Yankees’ roster. The disappointment and headaches and roster flummoxes? Gone. The outfield logjam? It just took one step closer to resolving itself. The most regrettable contract the Bombers passed out in the last 10 years? Ancient history.

Only in its place now rests a longer, more expensive, and all-around worse contract.


On Monday afternoon, the baseball world got riled up when Buster Olney reported that the San Francisco Giants discussed pursuing a trade for Ellsbury. This news comes days after Jon Heyman noted that the club had been canvassing the outfield market looking for any help they could find on the cheap.

Pursuing outfield help makes some sense for the Giants. Their current starting outfield features Chris Shaw, Steven Duggar, and Austin Slater. It took some convincing to accept that those are indeed real major league ballplayers, and not computer generated characters from MLB The Show.

The interest in Ellsbury raises some eyebrows, however, considering he didn’t play at all last year. When healthy in 2017, he authored a .264/.348/.402 batting line with a 101 wRC+. He didn’t even break the 100 wRC+ threshold in the two previous seasons. Farhan Zaidi must have serious concerns about his team’s complete lack of outfield depth.

In a vacuum, moving Ellsbury sounds like a no-brainer to the Yankees. They could rid themselves of an onerous contract, and maybe save a few bucks if they’re lucky. Most importantly, however, they would clear up a spot on the 25 man roster. His presence will create a lot of headaches for the team’s management this spring, and he would hamper a lot of flexibility on the bench.

The problem, however, is that the Giants appear to want Ellsbury in a bad contract swap. Olney speculated Johnny Cueto as a return for the center fielder, and that’s where things get dicey. Two reasons stand out as to why the Yankees probably wouldn’t make that deal — assuming the center fielder waves his no-trade clause.

1. If Ellsbury isn’t healthy, the Yankees can recoup insurance money

Cashman insists that Ellsbury will arrive to camp healthy and ready to reclaim his roster spot. Given his history of frequent and lengthy injuries, however, the Yankees will want to see that for themselves. There exists a non-zero chance that he won’t finish spring training in perfect health.

If that’s the case, then the Yankees can just sit back and recover some of the insurance money on the contract. According to Wallace Matthews, the team has a policy on Ellsbury similar to how the Mets did with David Wright. He explained that the club recouped $15,857,142.86 by letting him sit out for the year.

As long as that possibility exists, the Bombers have no urgency to move Ellsbury. They will let him go through spring training to see if he starts the season on the disabled list. In a way, that may be the most optimal outcome as far as the organization is concerned.

2. Cueto’s contract puts the Yankees in a worse position

Bad contract swaps happen all the time in baseball. Sometimes teams make the best of a poor situation. With Cueto, however, the Yankees wouldn’t be moving Ellsbury’s deal for an equally bad one. They would be taking on an even worse contract.

Cueto, 32, underwent Tommy John surgery in August. He is expected to miss the entire 2019 season. Sure, maybe the Yankees can recoup insurance money similar to how they did with Ellsbury. That’s not a sure thing, though.

The right-hander also has a longer contract. When the Ellsbury’s deal comes off the books, Cueto will still have another year and nearly $22 million owed to him. The whole point would be to get out from underneath the Ellsbury albatross, not prolong the ordeal.

There exists a chance that Cueto could be useful as a fifth starter, effectively taking CC Sabathia’s place once the southpaw retires. Cueto had a 4.52 ERA (4.49 FIP) in 2017, but had even worse peripherals last year with a 3.23 ERA (4.71 FIP). The juice isn’t worth the squeeze here.


For years fans have clamored for a way to trade Jacoby Ellsbury. In all likelihood, the front office felt similarly. The Yankees, however, have to approach such a move in a smart fashion. They should remember to be careful what they wished for. That monkey’s paw can be dangerous.