Midway through the 2019 season, a member of the New York Yankees organization assessed the laundry list of injured players, providing updates on rehabilitation schedules, the latest baseball activities for those ailing and possible timelines for their respective returns to the lineup.
When I brought up Jacoby Ellsbury, the response was an incredulous stare.
As in: Really? There was no expectation he would play this year, and in the end, Ellsbury didn't play much for the Yankees over the course of his seven-year, $153 million contract before his release this week. Ellsbury competed in 520 games over four seasons. He did not play in any games for the Yankees in 2018 or 2019 and won't in 2020, the last year of the contract.
That value deficit is why Ellsbury's deal will go down as one of the worst big-money contracts in baseball history. Using a Fangraphs search tool, Sarah Langs of MLB.com pegged the Ellsbury contract value at $63 million, so what the Yankees got in return was almost $100 million less in value. (Although the Yankees are now contending that Ellsbury violated his deal and say they do not intend to pay him the remaining $26 million due under his contract.)
What follows are some of the least productive free-agent contracts we've seen in baseball, among deals of at least $50 million.