Jacoby Ellsbury

Jacoby Ellsbury patrolled center field for the New York Yankees from 2014 to 2017, signed as a $153 million free agent to be the club's long-term leadoff man after two World Series titles in Boston. He gave the Yankees one healthy, productive season, two more wrecked by injury, one merely disappointing year sandwiched in between, and then never played in another big-league game after October 2017. It's one of the stranger tenures in recent franchise history -- a genuine star on paper who became a cautionary tale in practice.

Path to the Bronx

Before any of that, Ellsbury was one of the best players in the American League. Oregon State product, 23rd overall pick in the 2005 draft, and by 2011 he was putting up a season -- .321, 32 homers, 105 RBI, 39 steals -- that finished second in AL MVP voting behind Justin Verlander (who had one of the great pitching years of the era, so losing that vote isn't much of an insult). He'd already won a ring as a rookie in 2007 and picked up a second in 2013, months before he hit free agency.

That resume is exactly why the Yankees handed him seven years and $153 million on December 7, 2013. Brian Cashman needed a center fielder and a leadoff hitter, and here was a two-time champion with a Gold Glove, a Silver Slugger, and a track record of leading the league in steals three separate times. "I'm proud to be a New York Yankee," Ellsbury said at his introductory press conference, twelve days after the deal was announced. Boston fans, who'd just watched their World Series hero walk to the rival dugout, were not thrilled.

Yankees Career

The first year actually worked. Ellsbury hit .271 with 16 homers and 39 stolen bases in 149 games in the 2014 season, and for one season the contract looked reasonable (never mind that the team missed the playoffs anyway -- that one's not on him). Then the injuries started, and they never really stopped.

A sprained right knee wiped out about two months of 2015 and left him a shell of himself once he came back (he was hitting .324 before the injury, .224 after). The full-season numbers -- a .663 OPS, a career worst -- told the same story. He stayed healthier in 2016, playing 148 games, but the pop never fully returned either: nine homers and a .374 slugging percentage that wouldn't scare anybody. And in the 2017 season, the year the Baby Bombers went on their improbable ALCS run, Ellsbury was hitting .281 with real life in his bat until he crashed into the center-field wall on May 24, robbing Kansas City's Alcides Escobar of extra bases and taking a concussion for his trouble. Aaron Judge was becoming a phenomenon that summer. Ellsbury spent it losing his job to Aaron Hicks and never got it back.

The Injuries Win

What happened after that concussion is the real story of the Ellsbury contract. He played his final MLB games that October -- a DH start in the ALDS against Cleveland, pinch-running duty in the ALCS against Houston -- and simply never took the field again. A torn labrum in his hip cost him all of 2018. Plantar fasciitis cost him all of 2019. The Yankees, increasingly convinced they'd never get anything more out of the deal, converted the remaining money to non-guaranteed status, accused him of getting outside medical treatment without authorization, and released him on November 20, 2019, with roughly $26 million still on the books.

That triggered an actual grievance from the players' union, which dragged on until a confidential settlement in April 2022 (baseball's version of two exhausted parties agreeing to stop fighting in front of the kids). By the numbers, Ellsbury played in 520 of a possible 972 team games across the life of the deal -- about 53 percent -- and Pinstripe Alley has rightly called it the worst free-agent contract in franchise history. Brett Gardner ended up absorbing most of the outfield innings the Yankees thought they were paying Ellsbury to cover.

None of it shows up in a stat table, but Ellsbury still holds a big-league record: most times reaching base on catcher's interference. For a $153 million outfielder the Yankees signed to be their next great leadoff man, that's a strange thing to be remembered for. It's also, somehow, exactly right.