1. Chris Davis (7 Years $161 Million)
The Orioles are not in a good spot and one of the reasons is they are cash strapped because of the enormous deal they gave Chris Davis before the 2016 season. Davis signed a deal worth $161 million dollars over the span of 7 years and over the last couple of years he has been regarded as one of the worst players in the league. He hit just .179 in 2019 and in 2018 he was even worse putting up a .168 average. His home run output, which used to be the big draw for Davis, has dropped in every year from 47 in 2015 to just 12 last season. The end isn’t near for the Orioles either, Davis is slated to make $17 million from 2020 through the 2022 season.
2. Miguel Cabrera (8 Years $248 Million)
Cabrera has been a Detroit Tiger since 2008 and maybe they felt like they had to be loyal but after already showing signs of decreased value, the Tigers gave Cabrera a 8 year extension worth $248 million dollars. This deal runs until Cabrera is 42 years old and he has only put up 100 RBIs in 1 season since 2015. Cabrera is limited on the defensive end and with decreasing power and inability to run the bases it is unclear what they will get out of him in the coming years. He is slated to make $30 million dollars per year for the next 6 years including the 2020 season. This deal was a clear mistake by the Tigers and they will be feeling it for the foreseeable future.
3. Albert Pujols (10 Years $240 Million)
Pujols signed a deal similar to Miguel Cabrera’s but he has performed better and has stayed relatively healthy throughout the deal. Pujols had been a very good hitter for average but since joining the Angels he hasn’t hit over .300 in any season and over the last 3 seasons he has hit in the .240s. However, the Angels are almost free and Pujols only has 2 more years left in his playing contract. The interesting part of this contract is Pujols contract is after he is done playing he has a $10 million dollar “personal services” contract that will be paid, these types of deals have since been outlawed by the MLBPA. Overall this deal hasn’t paid off for the Angels and this isn’t the only deal by the Angels that made their way on our list.
4. Josh Hamilton (5 Years $125 Million)
Hamilton was drafted #1 overall way back in 1999 but after a flurry of substance-abuse issues his career took a detour. However he eventually became one of the best success stories in baseball after he came alive with the Texas Rangers. He was then awarded with a 5 year $125 million dollar deal with the division rival Angels. Unfortunately, the injuries started to pile up and in 2 years he only played 240 games for LA. He was then traded back to the Rangers and the Angels ate a majority of the money they owed to him. There are a lot of off the field rumors about what could have happened with the Angels but that doesn’t change the fact that this deal crippled the Angels financially.
5. Jacoby Ellsbury (7 Years $153 Million)
Jacoby Ellsbury had one of the best statistical seasons ever in 2011 with the Boston Red Sox when he hit .321 with 23 HRs 105 RBIs and added on 39 stolen bases. The combo of speed, power, and the ability to hit for average was rare and he was rewarded to go to the rival Yankees on a 7 year contract worth $153 million dollars. However, after a pretty solid first year it all fell apart for Ellsbury. He missed the entirety of the 2018 and 2019 seasons and after that the Yankees had enough and cut him with 1 year remaining on his massive contract. All in all given the injuries and struggles at the plate the Yankees got nowhere near the return on investment that they were looking for.
6. Jordan Zimmermann (5 Years $110 Million)
Another massive and questionable deal the Tigers handed out was the 5 year $110 million dollar deal they gave to Jordan Zimmermann, who had a successful career with the Washington Nationals. He wasn’t an aging player but it just hasn’t worked out for the Tigers who have rebuilding for a while now and are bogged down by massive deals to Zimmermann and Cabrera. He hasn’t posted an ERA below 4.52 in a season and has come nowhere near the 200 IP per year that he was floating around in Washington. 2020 will be the last year of his deal and after 4 years and posting an ERA of 5.61, the Tigers won’t be sad to see him walk after the season.
7. Carl Crawford (7 Years $142 Million)
Crawford put together amazing seasons with the Tampa Bay Rays at the start of his career and when his time came he made the jump to the big boys of the league signing a 7 year deal worth $142 million dollars with the division rival Red Sox. At the time the Rays weren’t competing so this deal made sense for both parties however, the production never returned to what we saw in the Tampa years. In his first season with Boston, Crawford hit .255 and in his second season he was only able to play a total of 31 games. After that the Red Sox had enough and moved Crawford and his contract to the Los Angeles Dodgers in exchange for 1B Adrian Gonzalez. All in all the Red Sox ended up only paying Crawford $43 million for 2 seasons and before cutting him the Dodgers paid $102 million to Crawford in exchange for 3 seasons of play.
8. Homer Bailey (6 Years $105 Million)
After pitching very well in 2012 and 2013 the Reds were anxious to keep their home grown star pitcher Homer Bailey in town and gave him a 6 year deal worth $105 million dollars. This deal panned out a whole lot like the Jordan Zimmermann deal with the Tigers. After getting paid Bailey was never the same and between 2015 and 2018 with the Reds, Bailey didn’t post an ERA below 5.56. He just could not get anything going and the Reds were forced to keep trotting him out on the mound given the amount of money that they invested in him. Bailey was eventually dealt to the Dodgers who ended up paying off the remaining $22 million dollars of his contract.
9. Rusney Castillo (7 Years $72.5 Million)
Over the last handful of years a big thing clubs have been doing is investing a lot of money in Cuban talent. It has worked out decently for players like Yasiel Puig but for Rusney Castillo it hasn’t worked out in terms of performance. He did get paid though, in 2014 he signed a deal worth $72.5 million over 7 years and as of now he has only played 99 games at the major league level. He has spent most of his time at the AAA level and hasn’t quite been able to break through despite the massive contract he signed. 2020 is the last year of his deal and he will collect somewhere near $15 million dollars despite not knowing if he will even get a major league at-bat.
10. Prince Fielder (9 Years $214 Million)
Before the 2012 season, Prince Fielder was awarded with a 9 year $214 million dollar deal after putting together a season where he hit .299 with 38 home runs and 120 RBIs. He was productive in the first couple of years since signing the deal but he was eventually traded to the Texas Rangers in 2014 in exchange for Ian Kinsler. He didn’t find much success there hitting under .248 in 2 of his 3 seasons. This contract is tough to judge because Fielder’s career eventually took a halt and he was forced to retire due to neck injuries that constantly held him back. Despite this he is still getting paid and despite not playing since 2016 he will be collecting $9 million dollars from the Rangers in 2020.