Three Ways the Yankees Could Dump Jacoby Ellsbury This Winter

The New York Yankees have finally cleared most of the worst contracts off their payroll, but one major albatross remains in center fielder Jacoby Ellsbury.

Even at the time, the New York Yankees’ decision to sign center fielder Jacoby Ellsbury to a seven year $153 million contract in December 2013 seemed like a major misstep, and now, after a steep decline in production during seasons two and three of the deal, it looks like one of the worst moves in the team’s recent history.

Assuming Masahiro Tanaka opts out of the remainder of his contract as expected following next season, the four years and $89.6 million owed to Ellsbury (including the $5 million buyout on his 2021 option) is easily New York’s largest financial commitment.

A big part of the rebuilding effort has been selling off their expensive veterans. They showed they are willing to continue what they started at the trade deadline last year by moving Brian McCann to the Houston Astros in November, and are also reportedly open to moving Brett Gardner and Chase Headley as well, although there hasn’t been a ton of interest.

Most analysts have taken it as a given that the Yankees are stuck with Ellsbury for the immediate future because of just how awful that contract is. New York’s only hope, unless they simply want to eat a huge amount of money to facilitate a trade, is to find a bad contract for bad contract swap that could benefit both sides.

Threading that unlikely needle means finding a player roughly as expensive and unproductive as Ellsbury whose club could use an outfield upgrade. Here are a few possibilities.

Detroit Tigers

By all indications, the Detroit Tigers are trying to cut payroll this winter, so them taking on a big money deal like Ellsbury’s seems counterintuitive. At the same time, the Tigers have a clear need in center field, with Anthony Gose and Jacoby Jones currently their best internal candidates.

They are still trying to compete in 2017, so if they were able to unload one of their own disappointing big money deals in exchange, there could be a fit. The Tigers have plenty of big contracts to choose from, but most of them are probably too good to swap for Ellsbury.

Their most onerous deals are Miguel Cabrera, who is still owed $212 million even if his 2024 and 2025 options don’t vest, and Justin Verlander, who was a serious AL Cy Young candidate last year. Despite the boatloads of money owed to them, anyone who wants to acquire them would probably need to part with some top prospects as well, making a deal for either guy unlikely.

The other two nine figure deals they have on the books might be a better fit following disappointing seasons. Jordan Zimmerman signed his five year $110 million contract just last offseason, and given the Yankees’ futile search for controllable starting pitching this winter, it’s possible they could see him as a viable bounce back candidate at age 31, even after pitching to a disappointing 4.87 ERA and 4.42 FIP in 105.1 IP while dealing with neck and groin injuries.

From 2012-2015, Zimmerman was one of the National League’s most consistent starters with the Nationals, accumulating a 3.13 ERA and 3.33 FIP over 129 starts over those four seasons, making him worth a combined 16.8 wins above replacement in that span according to Baseball-Reference.

Another possibility with the Tigers is their other big free agent signing from last year, Justin Upton, who is most likely available after hitting just .246/.310/.465 (108 OPS+) with 31 home runs and 87 RBI in 626 plate appearances

Aside from his flashy power numbers, Upton’s performance was pretty ugly in 2016, but he’s four years younger than Ellsbury and would give the Yanks another much-needed power bat. He’s owed $110.5 million over the next five years, so a straight one-for-one would help Detroit’s front office save around $20 million. New York would likely still need to sweeten the pot with a solid prospect or two for this to work.

Chicago Cubs

Jason Heyward was rumored to be the only big name free agent the Yankees would consider committing big money to last offseason because his youth made him a nice asset for a club on the cusp of a serious rebuild.

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It also came out last spring that New York came close to acquiring Heyward the previous winter as well, prior to the trade that sent him from Atlanta to St. Louis. The proposed deal was a ten-player that would have included Luis Severino, Aaron Judge, and Gary Sanchez.

Even after an ugly season in which Heyward hit .230/.306/.325 (70 OPS+) in 592 plate appearances and was relegated to a part-time player in the postseason, you have to believe there are those in the Yankees front office who would have some residual interest in bringing him on board.

Heyward is still just 27 years old and did win his fourth National League Gold Glove award. 2016 was the first time in the young man’s career that he was not an above average regular by Baseball-Reference’s wins above replacement metric. He’s accumulated 32.7 WAR over his seven-year career, and was worth over six wins each of the previous two seasons, which is superstar caliber production.

While Chicago signed Jon Jay to a one-year deal to patch over the hole left in center field by Dexter Fowler‘s departure. Even in his diminished state, Ellsbury would be a pretty big upgrade defensively and at the top of the lineup at a time when the Cubbies are gearing up for another championship run. It also helps them long term by shedding almost $100 million in committed money.

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Despite his poor performance in 2016, I’d much rather have Heyward than Ellsbury over the next few years, but this is probably the craziest of the four swaps I’ve proposed here because of how much more money the Yankees would be taking back at a time when they are trying to get under the luxury tax and trimming payroll. It would certainly be a fun gamble for New York though.