3. Jacoby Ellsbury
There was no question about Jacoby Ellsbury‘s talent. The question was whether or not he could stay on the field.
While he was a noted speedster, and the type of player that the New York Yankees needed, there was a question about what he was exactly. He had a 30-30 year in 2011, but had never reached double digit homers in any other year. Despite enough red flags for a May Day Parade, the Yankees gave him a seven year, $153 million contract.
Ellsbury was a disappointment when he did play, posting a subpar .264/.330/.386 batting line in his 2171 plate appearances. He hit just 39 homers and 86 doubles while stealing 102 bases. However, that production was not the worst part of Ellsbury’s contract.
He did not play at all in the final three years of the deal. He had hip and back issues that sidelined him for the entire 2018 season, with his hip eventually requiring surgery. That recovery, and subsequent setbacks, led to his missing the 2019 season as well. He was released prior to the 2020 season, and due to the pandemic, was the second highest paid player in the majors as he received his full salary. A $5 million buyout of a team option for 2021 finally got Ellsbury off their books for good.
Jacoby Ellsbury was a major question mark when he was signed by the New York Yankees. His injury problems reared their head and made that deal a disaster.