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Jacoby Ellsbury was the Yankees’ worst contract of all time

Although it was easy to be excited when they got him, Ellsbury became the worst investment in team history.

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

With great spending power comes great spending responsibility. While the Yankees have spent more money on players than any team in history, not all of their investments have been home runs. The likes of Kei Igawa, A.J. Burnett and Carl Pavano (all pitchers!) lived on as some of the worst mistakes in Yankees franchise history.

However, as another player’s Yankees career ends, a new contender has emerged, and he takes the cake. The Yankees’ fifth-most expensive acquisition of all time, he ended up providing less than 10 WAR over four mediocre seasons and two more years spent entirely on the injured list. Even in his buyout phase, there’s controversy, as the Yankees believe he violated the terms of his contract while injured.

Step aside, Igawa and Pavano, there’s a new biggest Yankees free agent bust of all time, and his name is Jacoby Ellsbury. What began as an electric signing ended as one of the most disappointing in MLB history, and easily the Yankees’ biggest waste of money.

It’s a shame, too. Ellsbury was a great player for the Boston Red Sox early in his career, but was honestly never worth the absurd deal the Yankees offered him. Ellsbury was a one-time All-Star in Boston, a one-time MVP finalist, a one-time Gold Glover and a one-time Silver Slugger. Instead, the Yankees paid him like he was a perennial award winner, blowing him out of the water with a seven-year, $153 million contract that seemed ill-advised from the get-go.

The Yankees were desperate. Robinson Cano was going to leave, and the Yankees didn’t know how to handle losing out on a marquee free agent, particularly one of their own. The Steinbrenners struck back by finding the biggest name they could, Ellsbury, and throwing oodles of cash at him. No matter how beloved a player is in Boston, anyone would trade in their Sox for pinstripes for a cool $153 million.

The problem was, Ellsbury was never really a fit in New York. The Yankees already had a lefty leadoff hitter with speed who played top-notch defense in Brett Gardner, and although two is usually better than one, adding Ellsbury really just made the Yankees’ lineup redundant. In the 2014 season, Ellsbury’s best as a Yankee, he most often batted third behind Gardner and a 40-year-old Derek Jeter. It was one of the least intimidating top-threes in team history – there sure was contact and speed, but almost no power threat.

All in all though, Ellsbury’s 2014 wasn’t bad. He put up the second-most home runs and RBI of his career, stole 39 bases and was generally productive, if not $21 million-a-year productive. It was after that season when the wheels really fell off for Ellsbury in New York.

Perennially a fragile player, Ellsbury succumbed to injuries for the rest of his time in pinstripes. His 2015 season started off well, but came crashing to a halt with a knee sprain that robbed him of his power and speed upon returning. When given the chance to start him in a must-win playoff game, manager Joe Girardi elected to sit his nine-figure man, the first major sign of trouble in paradise for Ellsbury.

Although he was mostly healthy in 2016, he wasn’t very good, putting up a .703 OPS and 88 OPS+. As he became ineffective at the plate, his speed and defense became the only reason to keep him in the lineup, and even those assets were declining. Although he rebounded somewhat in 2017, posting a .750 OPS and raking down the stretch, he was held hitless in the playoffs and ended his Yankees career as a nine-figure pinch-runner in the 2017 ALCS.

Although he showed up to spring training motivated in 2018, it became the last time Ellsbury ever played for the Yankees. An oblique strain sidelined him until April, when it was then revealed that he had developed a hip condition that became a torn labrum. Ellsbury missed the whole year, and was barely a thought heading into 2019.

Ultimately, a similar laundry list of injuries kept him out of commission again. His hip injury led to a foot injury, which became plantar fasciitis, and then finally a shoulder injury, which became the last straw for the Yankees. After not playing for over two years, and costing the team over $40 million in the process, the Yankees cut Ellsbury this winter, ending what became an embarrassing soap opera.

There are several reasons why this is the worst deal in team history. First, the Yankees were way out of line in their valuation and spending. They never should have invested a seven-year, $153 million deal in a speed-and-defense guy with a lengthy injury history. It was doomed from the start, and that’s not Ellsbury’s fault, per se.

When you compare it to the other bad deals in team history, nothing else comes close. Pavano, Burnett and Igawa combined to cost the Yankees about $142 million, which is still less than the team paid Ellsbury. While they provided even less production, none of their tenures lasted more than three years. Instead, Ellsbury became an albatross for six years.

There was buzz when the Yankees signed Ellsbury. I bought in – I had a jersey, a t-shirt and a bobblehead. He was an exciting player at his best, and he had some moments with the Bombers. He stole home twice, made several diving catches and hit two homers in the Yankees’ massive comeback win vs. the Orioles in April 2017. Still, with a contract like his, the expectations for Ellsbury were (unfairly) high, and he found a way to miss the mark on all of them.

Reports indicate that Ellsbury plans to play again in 2020 if given the chance, and fans should hope it works out for him. It would be a comeback story for the ages. Moving forward, the Jacoby Ellsbury experience shouldn’t be a cautionary tale for the Yankees to never spend again, but it can serve as a reminder moving forward that the Yankees should only spend on what they need, and not just the shiny toys.