When you are a young, there comes a point when you have to decide what it is you want to do with your life, and generally, that decision depends on your interests and the amount of money you hope to make. Many of us wish that we can make a good living by simply doing whatever it is we love, but in the real world, hardly anyone is lucky enough to find a job that they truly love to go to every single day. There are some exceptions though, like law enforcement, and the field of medicine, both of which can be especially rewarding because of their importance in society; but their is another profession out there that allows people to make a lot of money by doing something they have loved since childhood, and that profession would be a professional athlete.
There are those who would say that playing a sport professionally is easy, but it is actually quite difficult, as only a very select few have the skills and mindset to truly excel at sports at the professional level. In every professional sports league, including the MLB, athletes who perform receive contracts from teams that either have a long term associated with them, a boat load of money, or both; and although there are teams who are pleased with all of their contracts, there are some contracts that teams wish they could make disappear. In baseball, the contracts are guaranteed, which means that no matter what, a player will get paid every single penny in their contract, which would be fine, if teams did not sign players to terribly long and/or expensive contracts that restrict and mess up their budgets. That said, here are 15 current MLB contracts that are so bad that teams now regret signing them.
15 James Shields
For years, the Tampa Bay Rays have been known for producing talented starting pitchers, and for a time, James Shields was one of those pitchers, as they developed him from the time they drafted him in 2000. When he signed with San Diego in 2015, he inked a four-year, $75 million contract, and from the very beginning, it became apparent that he was no longer the pitcher he was in Tampa, as San Diego quickly became tired of his poor play and traded him to the White Sox the following season. Shields may be off to a good start this season, but it may not last long, as he has struggled to keep his ERA below 5.00 the past few years, and at 35 years old, it is hard to believe that he will be able to perform like he did in his younger days, which is unfortunate for Chicago as they have to pay him $16 million for three more seasons.
14 Ian Kennedy
When the Kansas City Royals won the World Series in 2015, they did so with the help of great pitching, and in order to take a run at another championship, they went out in the 2016 offseason and brought starter Ian Kennedy into the fold. The Royals signed him to a five-year, $70 million deal, which will see him make $13.5 million each of the next three seasons. which would be fine if Kennedy, for his entire career, did not struggle to keep his ERA below 4.00. If you ask any baseball insider, they will say that at this point, Kennedy's real value lies in the fact that he can eat up a lot of innings. Although going deep into a game helps out the bullpen, a pitcher whose main job is to eat innings should never be paid so much, because it hinders a team like the Royals who cannot afford a huge payroll. That is why they will regret signing him to such an expensive contract when it comes time to re-sign their best player, Eric Hosmer, next season.
13 David Wright
David Wright has been with the New York Mets since the team drafted him in 2001, and since then, he has gone on to become the team's captain, as well as the most beloved player on the entire roster. In November of 2012, the Mets signed Wright to a seven-year, $138 million contract, a contract which he lived up to in the first year, but if the last two seasons are any indication, the remaining four years may be a bit of a disaster for the team. Wright has had to deal with numerous injuries over the last two seasons, including a fairly serious spinal cord issue that he suffered last year which he is still rehabbing from, and which could force him into early retirement. Wright still has not played in a game this season, which will still see him get paid $20 million, and if he is forced to retire after this year, the Mets will still have to pay him a combined $47 million.
12 Phil Hughes
While with the New York Yankees, Phil Hughes was considered to be an up and coming star just like his former teammate Ian Kennedy who was mentioned earlier, and just like Kennedy, Hughes is getting overpaid. The Minnesota Twins signed Hughes to a 3-year $42 million contract extension in 2014 (which comes into effect this season), and since then, he has suffered several injuries, while also posting an ERA that is way above 4.00, and this year is looking like a terrible year as his ERA is nearly 5.75. Like Kennedy, Hughes is now good to just eat innings, but in doing so, he is taking up a good chunk of the Twins' payroll, as he will be making $13.2 million for the next 3 years, and based on his stats, its highly unlikely that Minnesota will be able to ever move him thanks to his salary.
11 Shin-Soo Choo
Before the start of the 2014 season, the Texas Rangers signed South Korean native Shin-Soo Choo to a seven-year contract worth $130 million, and although he has performed well as a designated hitter, his contract is still horrible. Since signing the contract, Choo has dealt with injury problems, injuries that last season caused him to play in just 47 games, and at 34 years old, these injuries have made his health a real concern. Including this season, Choo has four more years left on his deal, one which will see him earn $82 million, and if his body continues to break down, Texas will never be able to move him even if they want to. That's why his contract could foreseeably go down as one of the worst contracts in Rangers franchise history.
10 Pablo Sandoval
For six seasons (2008-2014), Pablo Sandoval played third base for the San Francisco Giants, and those seasons turned out to be the best of his career, as over that time he helped to lead the team to three World Series wins. It was because of his postseason success that the Boston Red Sox signed him as a free agent to a five-year contract worth $90 million, a contract that they have been regretting seemingly from day one. So far with Boston, Sandoval has not even been able to get his batting average to the .250 mark, and last season he missed the entire year with a shoulder injury. Also, his weight seems to constantly be an issue. Considering that he still has three years left on his deal, which will see him make close to $55 million, Boston is praying that he learns to hit like he did with the Giants.
9 Russell Martin
The Toronto Blue Jays have provided Canada with postseason baseball the past two seasons, and they did so by adding some much-needed talent and experience to their hard-hitting lineup, and one of those additions was Russell Martin. The Canadian catcher fits right at home with the team, and he has been a great help to the Jays' relatively young pitching staff, which was to be expected as he is considered to be one of the better catchers in the game. Toronto signed Martin to a five-year, $82 million contract in 2014, and although he has helped the team make it to the ALCS in two consecutive years, the Jays are now definitely regretting the amount of money they have to pay him. As a catcher, Martin is good when he is healthy, but he has been dealing with injuries this year and last year from playing too much,. When he does play, he cannot hit above a .240 average, which would be fine if Toronto was not paying him $20 million for three more years.
8 Matt Cain
Matt Cain was drafted by San Francisco in the 1st round in 2002, and has so far spent his entire career with the team as a member of their starting rotation, and over that time he has helped the team win three championships. It is because of his reliability that the team signed him to a five-year extension in 2012 worth $112.5 million, and for basically the entire length of that contract, he has performed well below the expectations of the team. Since singing that contract, Cain has finished every season with an ERA of 4.00 or above, including 2015 when finished the year with a 5.79 ERA, and this year is already looking to be another bad year as his current ERA is at 4.91. The Giants have regrettably paid Cain $20 million each year of his contract, but luckily for them his deal expires at the end of this season.
7 Adam Wainwright
The St. Louis Cardinals are still regarded as the best organization in all of baseball, primarily because they have a track record of developing young players and turning them into valuable members of the roster. St. Louis acquired Adam Wainwright in 2003 from the Braves, and since 2006, he has been a part of their starting rotation, where in that time, he became a big contributor to the team's last two World Series wins. It was because of his great performances during those years, that the Cardinals awarded him with a five-year contract worth $97.5 million in 2013, but unfortunately, they are regretting it now. In the first year, Wainwright lived up to his new deal, but the year after he missed the entire season due to injury, and for the past two seasons (including this year), he has posted an ERA above 4.60. If his numbers continue to deteriorate, St, Louis will regrettably still have to pay him another $19.5 million next year too.
6 Jason Heyward
It may have been a 108-year wait, but the Chicago Cubs finally won their third World Series last season, thanks to great pitching, and a roster that was mostly made up of young and incredibly talented players. However, there were also veteran hitters in the lineup as well. Jason Heyward, who despite being 27 at the time, had lots of experience, and the Cubs signed him last offseason hoping that he would help them win a championship. That help was pretty costly as they signed him to an incredible eight-year, $184 million contract. The contract will see Heyward make over $28 million this year and next, followed by another five seasons where he will get paid over $22 million a year. Despite coming off a Championship season, the Cubs have probably already realized that they drastically overpaid Heyward, because in less than two full seasons with Chicago, he has struggled to hit above .250.
5 Jacoby Ellsbury
Jacoby Ellsbury helped the Boston Red Sox to win the World Series in 2007 and 2013, and while with Boston, he became a player capable of batting over .300 and hitting over 30 home runs, which is why the New York Yankees nabbed him during free agency. New York signed him in 2014 to a 7-year deal worth $153 million, which will see him make just over $21 million every year, and when the Yankees signed him to that deal, they were expecting that Ellsbury would be hitting home runs in bunches because of how their stadium is built. Since signing the contract, Ellsbury's stats have been gradually declining each year, as his defense has become truly suspect at times, he has seemingly lost his home run power, he barely steals bases anymore, and his on base percentage has declined 3 straight years. At 33 years old, Ellsbury's decline will likely get worse not better, and the Yankees still have to pay him until 2020.
4 Homer Bailey
Here we have Homer Bailey, the last pitcher who will be appearing on this list, and he has so far spent most of his career as a part of the starting rotation for the lowly Cincinnati Reds. During his first three years as a starter, he constantly posted an ERA above 4.00, but the next two seasons, he lowered it to 3.68 and 3.49 respectively, which was apparently good enough for the Reds to re-sign him to a six-year, $105 million contract in 2014, which the team definitely regrets now. The reason for that is simple, because they could have used that money to try and re-sign Johnny Cueto, who is a far better pitcher. Instead they went with Bailey who over the past two seasons, thanks to injuries, has played in just 8 games where he has posted an ERA well above 5.00, He has also already missed the first couple months of this season with a shoulder problem.
3 Justin Upton
In 2005, Justin Upton was taken 1st-overall by the Arizona Diamondbacks, and at the time, he was viewed as a player with a lot of talent who was going to have great success in the MLB. While with Arizona, Upton proved to be a hitting machine who could reach a .300 batting average, and when he briefly moved on to the Atlanta Braves, he showed teams that he had the ability to hit close to 30 home runs. It was that power that led the Detroit Tigers to signing him in 2016. Upton has indeed hit home runs for the Tigers, but aside from that, his numbers have not been all that impressive, especially since his batting average while in Detroit has been below .250. Thanks to their division getting much better, the Tigers are not as competitive as they once were, and they are close to having to re-build, but to do so they will have to move contracts like Justin's. That may be impossible to do considering his contract still has four more years on it which comes with a $88 million price tag.
2 Prince Fielder
When the Detroit Tigers were still considered to be World Series contenders in 2012, they went out and signed first baseman/designated hitter Prince Fielder to a nine-year contract worth a whopping $214 million. Prior to coming to Detroit, Fielder was considered to be one of the best hitters in the National League, as he could hit well over .275, and knock out over 30 home runs a year, and in his two seasons with Detroit, he lived up to his contract during the regular season. In 2014 though, the Tigers decided to trade Fielder to the Texas Rangers, where he missed practically his whole first year with the team due to a neck injury, and it was ultimately because of his neck that he was forced to retire from baseball last year. With baseball contracts being guaranteed, this means that the Rangers are stuck having to pay Fielder $18 million for four more years to fulfill the contract even though he will never play in another MLB game.
1 Albert Pujols
From 2001 to 2011, Albert Pujols played with the St. Louis Cardinals, and during that decade, he was arguably one of the best hitters in the entire league, as he had a batting average well over .300 virtually every year, and he hit over 40 home runs multiple times. Combine those stats with his two World Series rings, and you can understand why the Los Angeles Angels handed him a 10-year contract worth an absurd $240 million, a contract that they deeply regret today. Since signing the contract, Pujols' highest average has been .285, and over the last three seasons, it has been well below the .265 mark. At 37 years of age, he can still hit home runs, but that is basically all he can do now, as all his other stats have been declining for years. Worse, he is still under contract until he reaches 41, and in that final year, he will be getting paid $30 million. Which begs the question, what were the Angels thinking?
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