Every Major League Baseball team prioritizes signing the best talent possible to ensure they have the best chance at winning the ultimate prize, the World Series. See, free agency can make or break a team for the present and future.
A team like the Chicago Cubs, the reigning World Series champions, for example, saw themselves led by one of the best free agent signings in recent history, Jon Lester. Pitching alongside John Lackey, Lester helped dominate opposing teams to lead the Cubs to the World Series win. However, the Cubs gained familiarity with the other side of the business as Jason Heyward, the prized free agent signing of the offseason before, turned out to be a total bust. Every team has their fair share of strong free agent signings and free agent busts. The goal is to maximize the strong signings and minimize the busts in order to create the best roster possible. And the the teams that succeed most in this endeavor go the furthest and end up hoisting the World Series trophy when all is said and done. Let's take a look at some of the bad deals, meaning the deals that teams will find themselves regretting in the immediate and/or in the future.
15 Jason Heyward
As we already mentioned, one of the few negatives on the Chicago Cubs team that broke their over-a-century-long World Series drought was Jason Heyward. Heyward was signed to be a great boom defensively and offensively to the Cubs roster, but instead failed to contribute offensively at all, while his defense failed to make any kind of a significant difference. Heyward still has around $200 million left on his contract, one that the Cubs are already wishing they could get rid of. Theo Epstein was recently chosen as the top leader in the world of baseball, but even the best ones make mistakes. Heyward's contract is among the worst in the entire league and that is not about to change any time soon. It's a disaster.
14 Zack Greinke
When the Arizona Diamondbacks signed Zack Greinke away from the Los Angeles Dodgers, they thought they pulled a fast one on one of their chief rivals. Instead, it turns out they were doing a favor to the Dodgers, as Greinke has not performed close to the expectations the Arizona Diamondbacks had for him. Now the Diamondbacks are simply hoping their $34 million pitcher can provide them with top starter success, otherwise they will be paying nearly double what the average 2nd or 3rd starter makes in Major League Baseball. Oh, and by paying him that much, they also prevent the Dodgers from having to spend all of that money on him. It's not what you want.
13 Ian Desmond
Ian Desmond has had one of the strangest careers of any player in all of Major League Baseball. He went from a fringe prospect in the Washington Nationals' system, to a strong prospect, to a somewhat solid contributor, to a solid contributor, to one of the most useful players, and finally to a useless player, all in the span of a few years. He went through all of the roles with Washington, then signed with the Texas Rangers. With the Rangers, he moved to center field from shortstop, a strange move for the player. This offseason, he signed to switch positions again, this time back to center field with the Colorado Rockies. It's a strange signing with zero evidence to suggest it will work.
12 Rich Hill
Alright, we already know what you are thinking. What could possibly be the disadvantage to signing a pitcher to a three year deal? If he does not work out, the Los Angeles Dodgers can simply replace Rich Hill with someone else, right? Well, the Dodgers will want to keep giving Hill chances to get healthy and perform, leading to their misunderstanding his value to the team, and failing to acquire other players. Wouldn't the Dodgers be better off if they had acquired, say, Chris Archer or Jose Quintana instead? The Rich Hill signing was a short term fix that we believe by the second year will have solved nothing. But hey, teams love to sign the players they already have familiarity with for some reason.
11 Kendrys Morales
Kendrys Morales went unsigned for a long portion of the 2014 season, something that seems to have been forgotten by many Major League Baseball teams. The Kansas City Royals brought him on board for 2015 and 2016, and admittedly, he did help them win a World Series title, and flags fly forever. However, those same Kansas City Royals allowed him to leave in free agency without even making any attempt to bring him back. Seems suspicious if he's that good, no? Well, we think the Royals knew something that some other teams didn't, such as the team that ended up signing Morales, the Toronto Blue Jays. Even worse, the Blue Jays signed Morales to replace Edwin Encarnacion, arguably their best hitter besides Josh Donaldson.
10 David Price
While the Boston Red Sox went all-in this offseason by acquiring Chris Sale, one pitcher was noticeably missing from their opening day rotation. And that pitcher was David Price, the prized signing of the offseason prior. Price was believed to be needing Tommy John surgery, essentially the worst-case scenario for any starting pitcher. Luckily for the Red Sox, Price simply needs to rehab his elbow. But unluckily for the Red Sox, Price struggled yet again last post-season, continuing a career-long stretch of post-season struggles. At this point, this is simply who David Price is as a pitcher. He will pitch pretty well in the regular season, then completely fall apart in the post-season. That's not what you want if you want to win a World Series.
9 Pablo Sandoval
While David Price has struggled throughout his entire postseason career, the Boston Red Sox also signed a different player due in part to his postseason success. The Red Sox signed Pablo Sandoval in the year 2015 to take over their vacant third base position. Sandoval immediately brought plenty to the table....when it comes to controversies. Sandoval has provided little to no production to the Red Sox, while instead providing plenty of headaches to the organization surrounding his weight and inability to produce on the field. The Red Sox have Sandoval back at third base this season, hoping he can provide even a bit of the production they expected of him when they signed him to his long-term contract back in 2015.
8 Aroldis Chapman
Aroldis Chapman was one of the most critical components to the Chicago Cubs' success the year they brought him aboard in a trade with the New York Yankees. The Cubs surrendered a bevy of prospects in the deal, but it turned out to be completely worth it, as the Cubs went on to win the World Series for the first time in 108 years. However, Chapman gave a preview to what his future looks like when he blew the save in Game 7 of the World Series. As a pitcher who relies completely on his velocity, when he loses that velocity, he will be lost. The Yankees signed him to a five-year deal, and during that span they will see him decline into a poor pitcher.
7 Justin Upton
Justin Upton provides the Detroit Tigers with some power and home runs, but not much else. He can no longer serve as a threat to steal any bases, and he does not play the outfield very well anymore. So the Tigers spent a whole lot of money for the next bunch of years essentially to buy some home runs. Teams can buy homers from other spots, however. For example, the New York Yankees signed Chris Carter, who hit 41 home runs last season, for only $3 million in the offseason. The Tigers did not need to spend that much on Upton, and now they have a long-term, weak contract on their books that they have to deal with for the short and long-term.
6 Jeff Samardzija
Jeff Samardizja was once a star wide receiver for the Notre Dame Fighting Irish. He was also once a top starter for the Oakland Athletics and Chicago Cubs. In fact, Samardzija left the Cubs just before they took off as a powerhouse in Major League Baseball and won their first World Series in over a century. So why then, may you ask, did the San Francisco Giants determine Samardzija was worth a mega-contract to join their team as a top three starter? Well, uh... we don't understand this one either. The Giants needed a starter, but they surely did not need this starter. Samardzija is an average pitcher at this point in his career, and not worth nearly the big bucks the Giants are paying him.
5 Jordan Zimmermann
There seems to be a bit of a trend here where players leave competitive teams, join other competitive teams, then fail to succeed in their new organizations. We believe this may be due to the teams that let the players go knowing that those respective players can no longer contribute enough to winning organizations to be worth what they are going to be paid. Why else would a player like Jordan Zimmermann, one of the top pitching free agents a couple of years ago, be let go by the Washington Nationals, a team desperately trying to succeed in the post-season? The Detroit Tigers should have seen the writing on the walls rather than signing Zimmermann to a big, long-term deal to lead their rotation.
4 Alex Gordon
Another reason teams sometimes sign players to large contracts is because of the success they had with their respective Major League Baseball organizations. One of the prime examples of this is Alex Gordon. Gordon is not worth the 4-year, $72-million contract he signed after he aided the Kansas City Royals in winning a World Series, but let's go back through the sentence. Winning a World Series serves as the key words, as once those words enter the fold, teams become blind to the negatives of players. Despite Alex Gordon failing to provide any great contributions that the average player cannot contribute, Gordon received a mega-contract from the Royals. They are already wishing they didn't hand the deal to him, and that will continue.
3 Homer Bailey
Homer Bailey is one of the few actual Major League Baseball talents left on the Cincinnati Reds' roster. The Reds signed Bailey to an extension despite looking to go for a full rebuild, then immediately saw their top starter, who we should mention has never shown All-Star stuff or the stuff to deserve a mega-extension, go down and require Tommy John surgery. So not only did Bailey cost the Reds big time on the payroll when they are in the midst of trying to lose games anyway, but he also is wasting their money until he returns from injury. He shouldn't even be that good when he returns from injury anyway. Oh, and the guy's name is Homer! In baseball!
2 Scott Kazmir
Scott Kazmir was reaching the mid-80s with his fastball in Spring Training! Oh wait, we said fastball, not change-up. Yikes. That's not good. Kazmir will make $18 million for each of the next two seasons for the Los Angeles Dodgers, who gave the aging lefty a hefty contract for some unknown reasons. Kazmir was not very good in his first year on the contract, and is already both injured and seeing his velocity drop big time in the second year of his contract. We're not sure Kazmir will be able to salvage this contract at all, and with the Dodgers also signing Rich Hill to a questionable contract, there are a lot of questions to go around when it comes to the Dodgers rotation.
1 Wei-Yin Chen
Wei-Yin Chen was always a third or fourth starter for one of the worst team in the entire league when it came to pitching in the Baltimore Orioles. Owning one of the worst rotations in all of Major League Baseball, the Orioles still chose to put Chen in the third or fourth starter role rather than giving him one of their top two slots. With that in mind, no team would possibly give him top two starter money, right? You would think so. But the Miami Marlins had other ideas. The Marlins gave Chen the money of a #1 or #2 starter, and are now seeing the ramifications of it. Chen is their fourth starter already, showing they had no idea what they were doing.