Contrary to the prevailing sentiment of today, teams like the Yankees and Dodgers need to succeed in various areas in order to build perennial contenders, and it goes beyond simply letting your money secure a postseason ticket. Nothing quite helps corroborate that, as a trip down memory lane to the 2013 season, one in which the Yankees lucked into an 85-win campaign and decided to do something about it, strengthening themselves all while weakening their biggest rivals by signing Jacoby Ellsbury on the open market — a deal that has lived on in infamy for the Yankees.
Jacoby Ellsbury
Signing Date: December 7, 2013
Contract: 7 years, $153,000,000
With the benefit of hindsight, who knew the Yankees would’ve been better off re-signing Curtis Granderson, who was coming off the worst season of his career, rather than diving in the deep end of the pool of the free agent market for outfield help? It was the thing we often ask teams to do. Ellsbury was the signing that didn’t pay off, but the Yankees could’ve just as easily gone after Shin Soo-Choo and been underwhelmed with his solid but still disappointing numbers as a Texas Ranger. In fact, one might argue that Choo would’ve been a better fit, considering the sole productive player remaining on the Yankees lineup from that previous campaign was Brett Gardner, a traditional center fielder. Adding top players is always welcomed, but at the time, it was irrefutable that part of the value of both Gardner and Ellsbury lay in what they delivered as hitters while playing center field — move them to a corner spot, and it’s an entirely different ballgame with those hitting stats, which is what the Yankees ultimately decided to do.
The comment about Gardner is true in part because Robinson Cano, the Yankees’ best player in 2013, had reached the open market as well. When Ellsbury was signed, there were some reports that didn’t rule them out from bringing back Cano, but as we know now, the Mariners delivered an offer New York was unwilling to match, putting even more pressure on Ellsbury to deliver as one of the key pieces of that new-look Yankees team. Much like there ultimately was a rather large gap between what the Yankees were willing to offer and what Cano ultimately received, the same could be said of Ellsbury and the Red Sox to an even larger extent — it quickly became clear he wasn’t coming back to Boston.
It should be noted that rather obvious concerns directly affected the perception of Ellsbury’s signing, one not necessarily welcomed with unanimous approval. The risks were rather evident for a player who relied heavily on speed as a part of his game and who had missed large chunks of two of his previous four seasons before reaching free agency. Unfortunately, even the short-term gain the Yankees thought they were acquiring didn’t last nearly as long as the team originally hoped.
Following in the footsteps of Johnny Damon, who also left the Red Sox to move to the Yankees in free agency as a speedy outfielder with a great hit tool, Ellsbury’s opening year in the Bronx was anything but a preview of what was to come. Ellsbury registered the most games he had since that runner-up MVP campaign in 2011, playing in 143 of 162 for the Yankees in 2014. Repeating the struggles of 2013 as a team, the Yankees labored their way through a mid 80s win campaign with Ellsbury’s addition nullified and then some by Cano’s departure. An aging lineup struggled to produce, particularly in the infield, wasting an outstanding debut season from Masahiro Tanaka, who really provided a boost to the starting staff.
During the 2015 season, the injury issues started to creep in, and while he was still able to play well over 100 games, Ellsbury’s numbers took a dive following a strained right LCL, leading to a career-worst .663 OPS and only 21 steals on 30 attempts, severely lowering his success rate on the basepaths. The Yankees managed to return to the playoffs that year as a Wild Card team, but Ellsbury didn’t feature in the starting lineup against the left-hander Dallas Keuchel and the Houston Astros; instead, he was a pinch-hitter for Chris Young.
Through a variety of factors, even before the injuries truly started to sideline Ellsbury for massive chunks, his numbers had already regressed to the point of making his contract a poor investment. Ellsbury remained healthy for the 2016 season, but his 88 OPS+ and disappointing numbers on the basepaths led to a pretty mediocre campaign. The Yankees, as a team, also took a step back and missed the playoffs for the third time in four seasons.
Following a similar path to the 2015 campaign, Ellsbury once again missed a little under two months in 2017, this time due to a concussion tracking a fly ball in center field in Kansas City in early May. Ellsbury had shown some promise before getting hurt, and he wrapped that year with a solid .750 OPS, a complementary piece in a Yankee team that went all the way until Game 7 of the ALCS against the Astros. Despite those numbers and Ellsbury being healthy for the playoffs, it was Aaron Hicks starting in CF for the Yankees throughout the duration of that postseason — Ellsbury got a limited role coming off the bench and didn’t record a hit in nine plate appearances.
In Game 4 of that ALCS, Ellsbury entered as a pinch-runner and came around to score in a 6-4 win—that would be his final play as a Yankee, with a plethora of injuries preventing him from ever taking the field again, unable to perform for the final three years of his deal. Ellsbury came into spring in 2018, having lost his starting center field role to Hicks. Sidelined due to an oblique injury, Ellsbury later had to undergo hip surgery that kept him out for the remainder of 2018. He was never able to return to a big league field, rehabbing without success for the entirety of 2019.
Unable to get on the field for two years, the Yankees released Ellsbury after the 2019 season in a move that later spurred a legal battle between the player and organization for the compensation of the remainder of his contract. The Yankees filed a grievance in an attempt not to pay the remainder of roughly $26 million they still owed Ellsbury, claiming the player had gone outside of the organization without adequate permission to get treatment. Eventually, a settlement was reached for an undisclosed amount. On top of saving some of that money, the Yankees got out of luxury tax problems, as paying the full figure to Ellsbury would’ve meant going over a second luxury tax threshold, resulting in a loss of draft picks.
When you sign any big-time free agent, there is always an assumption you’re paying for the present while assuming a certain loss down the line. The problem with Ellsbury is that both the short-term and the long-term went well below expectation, making for one of the worst free agent contracts this franchise has ever handed out — and if you want to add salt to the wound, the Red Sox selected Michael Kopech in the 2014 MLB Draft with the compensation pick they received for the departure of Ellsbury. Kopech didn’t do much with the Red Sox, but he was a key piece in the Chris Sale trade, the ace of Boston’s 2018 World Series title.
See more of the “50 Most Notable Yankees Free Agent Signings in 50 Years” series here.