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.
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.