1. The Jacoby Ellsbury signing
Jacoby Ellsbury had a very puzzling career with the Boston Red Sox. He was a really solid leadoff hitter with terrific speed. In 2009 he led the league with 10 triples and 70 (yes 70) stolen bases. Despite not hitting more than nine home runs in a single season in the first 3 full seasons of his career, Ellsbury hit 32 in 2011. It felt out of nowhere, and it really was.
That 2011 season was absurd from Ellsbury. He slashed .321/.376/.552 with 32 home runs and 105 RBI. He stole 39 bases and hit 46 doubles as well. He was an all-star, won a Gold Glove in center field, took home his first Silver Slugger award, and was the MVP runner-up. Just a monster year.
Ellsbury never came close to repeating those power numbers, but stole 52 bases and hit just below .300 in the 2013 season for Boston serving as their leadoff hitter. He was a big part of their World Series team that year.
Ellsbury was a free agent after that 2013 season and signed a seven-year $153 million dollar deal to leave Boston and go to New York. Things couldn’t have gone much worse for the former All-Star.
He had a decent debut season, stealing 39 bases and hitting 16 home runs with a .747 OPS and a 111 OPS+ in 149 games. In the three seasons after that, Ellsbury had an 89 OPS+ in 371 games played. He did not record a single postseason hit as a Yankee after winning two World Series titles with Boston.
Ellsbury was a below-average hitter for most of his first four seasons with the Yankees and didn’t play in the final three years of his contract because of a multitude of injuries. Normally stealing an All-Star from Boston would feel good for Yankee fans, but Ellsbury’s stay in the Bronx was an absolute disaster.