Big contracts are a risk, especially for pitchers. Age, injuries, environment, and even luck become big factors that influence how a player ends up performing. However, teams still do like to ink pitchers to big deals, some of which become great investments while others not so much. Here’s a list and analysis of the biggest 7 contracts in MLB history:



#7 Barry Zito: $126 million, seven years

It’s really hard to remember nowadays that Barry Zito was a Cy Young winner in 2002. During his seven-year stint with Oakland, Zito was a pitcher with very good results, even though his peripherals raised a lot of questions. After that period, he was shipped across the bay to answer the call of a colossal $126 million contract he signed with the Giants.

All of the questions about his peripherals were answered as he has consistently underperformed. You’ll often hear that his was probably the worst contract ever for a pitcher, and that claim is certainly justified by the numbers he has put up in San Francisco (up to 2012): 4.47 ERA, 4.57 FIP, 58-69 W-L.

Some would argue that Zito hasn’t been a complete loss, as the Giants have won two World Series in the time he’s been there, but one has to think that they have won despite Zito and not necessarily because of him (this without mentioning that he was actually left of the 2010 postseason roster).





#6 Matt Cain: $127.5 million, six years

During the course of the 2012, Matt Cain signed this monstrous deal, which was the second largest contract ever for a pitcher that was not a free agent. The Giants bought a very neat package in Cain: he’s definitely an elite pitcher who has been posting excellent results for years (3.09 ERA from 2008 to 2012) and who can be a workhorse on top of the rotation (Cain has pitched at least 200 innings in every season since 2007).

While some people think that players get relaxed after a big contract, Cain actually ended up posting his best season in 2012, reaching career highs in wins and strikeouts, and career lows in ERA, BB/9 and WHIP. Any long-term contract carries some risk, of course, but there’s no denying that things are looking good for the Giants with this contract.





#5 Johan Santana: $143 million, six years

One of the best left-handers to pitch in the majors in the

past few years, Santana ended his tenure with the Twins on a high note and looking to get a huge pay for his services. And forth came the Mets with a huge deal for Santana, handing him a six year deal that could extend up to a seventh season and $150 million.

Over the first three years of his contract, Santana was as good as advertised, posting a 40-25 win-loss record to go with a nice 2.85 ERA. However, he ended 2010 on a low as he had to be shut down because of shoulder problems that also held him out of any baseball activity in 2011. He came back strong in 2012, even throwing the first no-hitter in Mets history. This no-hitter took 134 pitches out of him and, after that, he wasn’t the same again. The whole mess ended up with him getting shut down again.





#4 Cole Hamels, $144 million, six years

Cole Hamels’ situation was very similar to the scenario I mentioned above for Matt Cain: an elite pitcher that signed a big contract extension to avoid hitting free agency. Hamels has also established himself as the type of guy that will give you 200-plus innings of pure quality every year, which isn’t something you could say about a lot of pitchers.

Hamels is often overshadowed by the names of Cliff Lee and Roy Halladay in the Phillies rotation, but make no mistake: he is a premier pitcher and he was paid like one.





#3 Zack Greinke: $147 million, six years

Greinke was the name in everybody’s mouth after the 2012 season. The whole market waited for him to sign before moving, and there were many rumors that he would be getting the biggest contract in history. While that didn’t happen, he came very close, signing with a Dodgers team revamped by pure economic power.

Greinke has been a great pitcher over the past few years, striking out at least 180 batters in each of his past 4 seasons and having some of the best peripheral stats in the sport. He has also been mostly healthy (except for an injury he sustained while playing hoops in the offseason). Even though some fear he could have a relapse of his anxiety problems in a bigger market like LA, there’s no denying that this could be a great buy for the Dodgers.





#2 CC Sabathia: $166 million, seven years

After years of dominance with the Indians (and a short stint in Milwaukee), Sabathia’s signing came during a Yankee spending spree in the 2008-2009 offseason, in which they also inked AJ Burnett and Mark Teixeira.

CC Sabathia is one of those rare examples of a pitcher actually earning every dollar in his contract. He has pitched at least 200 innings in every year since 2007, always keeping an ERA under 3.5, and he’s won at least 17 games on every season since his contract, except 2012. Sabathia is a pitcher with workhorse mentality, elite skills and an incredible consistency that have, so far, been worth every penny spent on him.





#1 Felix Hernandez: $175 million, seven years

King Felix’s deal is the most recent case of a huge contract, as he broke into the history records with a gargantuan seven year deal. The former Cy Young has been one of the best pitchers in the game for years, buried under the mediocrity of the offensively challenged Seattle Mariners. Not only that, but he’s also been the face of the franchise for years and, as a player that is just entering his prime, many big things are expected from him.

It’s hard to criticize the Mariners for the deal. Felix has been nothing but greatness for years, even though his win-loss record will never show it due to the low run support he gets. Since 2008, he’s the pitcher with the 6th biggest WAR and the 3rd pitcher in innings thrown.

Sure, there are a few well based concerns over a drop on his velocity and some lingering shoulder issues that have some people worried about the long contract but with a player like Felix, it is definitely worth it.



Editor Note: Why did we pick the Top 7? Because their contracts have a combined value of just over $1 Billion.



