The last two off seasons have a been a nightmare for MLB free agents.  In a time of big revenue for top market teams you would think that money would not be an issue and we would see the spending wars of the mid 2000’s.  What was once an arms race has turned into nothing more than a pity party.  Just ask Mike Moustakas and Greg Holland last season. The value of prospects, international money and draft picks has changed the way a lot of team construct their rosters. While there has been a culture change for most front offices, mistakes of others are also a factor in longer term deals.  These are the worst five contracts that have affected the current market.

5. Jordan Zimmermann, Detroit Tigers, 5-year $110 Million

Zimmerman was a hot commodity when he hit free agency after the 2015 season. All Star appearances in 2013 and 2014, winning 13 games in 2015, Zimmerman was arguably the biggest free agent starting pitcher name on the market.  The Tigers bit on the hype and signed Zimmerman to a hefty contract. At the time it looked like a great fit for a Tigers team that was looking to contend for a championship going into 2016.  The wheels feel of for Detroit and they feel into the bottom of their own division.  Zimmermann was not much help carrying a 5.13 ERA in three injury-plagued seasons in Detroit, and he’s still owed another $25 million in each of the next two seasons. 

Zimmerman’s poor play and massive contract have may him an impossible trade piece. Luckily for the Tigers Zimmerman should come off the books around the same time that the young pieces they have assembled can take form.

4. Albert Pujols, Los Angeles Angels, 10-year $240 Million

Albert is not higher on this list because he has been able to produce some over his seven seasons with the Angels. Producing two seasons of +4 WAR and one season hitting 40 HR.  Overall though this contract has put the Angels in a tough position.  Currently having the best player in the world on your roster you would hope to add something around him.  The Pujols contract and inability to play a position has hamstrung the organization.

Pujols was able to give the fans some memorable moments hitting his 500^th and 600^th homeruns as a member of the Halos.  Other than that, he has primarily been a burden. He is also due another $87 million over the next three seasons. Hopefully, it was all worth it for the Angels, who have gone just 576-551 with one playoff appearance since signing him.

3. Jacoby Ellsbury, New York Yankees, 7-year $153 Million

Second place in MVP voting in 2011, 52 steals in 2013.  Speed, power and defense, Ellsbury seemed to have it all going into the offseason of 2013.  The New York Yankees made an offer to the 29-year-old that seemed like a smart move on a great player in his prime.  Fast forward to 2019.  Ellsbury is entering the 5^th year of his massive deal, still due another $42 million over the next two seasons not including the buyout of another $5 million in 2022 the Yankees have basically considered him a wash.

Jacoby didn’t play a single game in 2018 and has already been considered an afterthought in the stacked Yankee outfield.  If he is healthy enough to play, would they really even play him? His first season in pinstripes was solid with an OPS of .747 adding 39 steals, that’s basically all they got or their $153 million.

2. Pablo Sandoval, Boston Red Sox, 5-year $90 Million (2014)

In 2015 Pablo Sandoval cashed in on his Giants playoff heroics.  The Red Sox signed Pablo to a 5-year, $90 million-dollar contract.  The most memorable moment in his Red Sox career was when he took a swing and broke his belt in the process.  That belt took a bigger beating then the ball ever did off his bat while in Boston. Three seasons in Boston Sandoval played a total of 161 games.  That’s right a five-year contract got the Red Sox the equivalent of one season. In those games Sandoval hit .237 with 14 homers.  Not much more to say about this one.  His time in Boston effectively ended the legend of the Kung Fu Panda.

1. Chris Davis, Baltimore Orioles, 7-year $161 Million

Chris Davis was always boom or bust player. When Davis signed his “mega deal” homeruns were not at a premium. From 2013 to 2015 the MLB average for homeruns per game was only .94.  Not realizing that the change in MLB culture was coming the Orioles thought they had a unique and mesmerizing player.  At the time of the deal it made sense, looking at it now makes Orioles fans sick to their stomach. 

Davis hasn’t just been bad, he has been historically awful. Hitting just .168 in 2018 Davis found himself out of the lineup for the last place Orioles.  This team was in last place and still couldn’t find a way to play him!  Oh, and he’s still owed another $94 million over the next four seasons. There are no signs that this is going to get any better for him — or for the team.