Top 10 Highest-Paid Starting Pitchers in the MLB

Starting pitchers have a pretty sweet gig. Pitch for a couple hours every fifth game and then enjoy a few days off sitting around watching baseball and spitting seeds. Some starting pitchers, like former Atlanta Brave John Smoltz, have even been known to golf frequently on their off days. Furthermore, if a starting pitcher is successful and wins approximately two thirds of his appearances, he can expect to have solid job security and get paid handsomely.

The latest example of this is the Los Angeles Dodgers' Clayton Kershaw and the New York Yankees' Masahiro Tanaka. Kershaw, who on January 15 signed a record-breaking deal worth $215 million over a seven year period, was joined by the unproven Tanaka eight days later in the rich-pitchers club as he signed a seven-year deal of his own worth $155 million. Baseball teams recently have begun to see just how valuable starting pitching can be in today's game and over the last several years they have invested immense funds on talented arms. However, there is an inherent risk for teams if a pitcher doesn't live up to a certain standard or fights injuries after he inks a deal.

Some recent investments have been major flops, just look at two contracts that expired at the end of 2013 with Johan Santana and the New York Mets, and Barry Zito and the San Francisco Giants. Still, GMs and baseball owners know just how valuable good pitching can be and continue to push forward undeterred. Without further ado, here's a look at the top-paid starting pitchers in baseball based on annual per-year average.

10 Adam Wainwright, St. Louis Cardinals - $19.5 million per year

Last May the Cardinals invested some big money in their ace Adam Wainwright, signing him to a five-year contract extension worth $97.5 million. The tall 6'7" pitcher has had some of his best years since 2009, going 72-41 over four full seasons for a .637 win-loss percentage. An elbow injury that kept him out all of 2011 had some worried he might not be the same pitcher afterwards, but he's proved doubters wrong with an exceptional year in 2013. Coming off his injury in 2012 with a decent 14-13 record, Wainwright went 19-9 in 2013 and finished second in NL Cy Young Award voting.

The Cardinals hope the 31-year-old can once again lead a young and talented staff, which includes 22-year-old Michael Wacha who became a household name in the 2013 playoffs. The Cardinals hope Wainwright delivers a fourth season of 19 or more wins in the past six years, especially since they'll be paying him more than $570,000 per appearance in 2014.

9 Matt Cain, San Francisco Giants - $21.25 million per year

Matt Cain entered the 2012 MLB season as the highest-paid right-handed pitcher when he signed a six-year deal worth $127 million. Cain inked the deal days before the 2012 season and he proved to be worth the money, at least for the year. The former first-round pick went 16-5 in 2012, cementing himself as the Giants' ace as he led them to their second World Series title in three years.

However, as great as Cain was in 2012, 2013 is a year he'd probably like to forget. The 29-year-old went 8-10 in 2013 with a 4.00 ERA, not near the production you'd expect from a pitcher making over $21 million year. Cain's contract has been somewhat suspect from the beginning as he's never placed higher than sixth in NL Cy Young Award voting and has posted a career win-loss percentage of .514, with a 93-88 career record. Based off his 30-game appearance in 2013, Cain was making a cool $708,000 per start.

8 Masahiro Tanaka, New York Yankees - $22.1 million per year

The newest edition to the high-paid pitchers club is Masahiro Tanaka, who signed with the New York Yankees on Wednesday, January 22 for the eighth richest annual deal among pitchers. His deal is worth $155 million over seven years, meaning the Japanese transplant will make an average of $22.1 million per year, the third-highest salary on the team behind Mark Teixeira and CC Sabathia.

Tanaka, who has yet to throw a pitch in the majors, was very impressive playing in Japan last year, compiling an unheard of 24-0 record with a 1.27 ERA leading his team, the Ratuken Golden Eagles to a Japan Series title. It will be interesting to see how the 25-year-old holds up against MLB competition, but luckily for the Yankees there is an out for the organization if Tanaka flops in the majors, as an opt-out clause has been put in after his fourth year in 2017. With the success of previous pitchers from Japan, like the Texas Rangers had in 2013 with Yu Darvish, it's not too big of a surprise the Yankees made such a high-risk/high-reward investment.

7 6 (tie). Cole Hamels, Philadelphia Phillies - $24 million per year

During the middle of the 2012 MLB season, Cole Hamels agreed to terms with the Philadelphia Phillies on a six-year contract extension worth $144 million. The deal was a way for the Phillies to reward Hamels for his .594 career-win-loss percentage, having gone 85-58 in his first seven years in the majors.

Unfortunately for the Phillies, since the extension the 30-year-old left-hander has struggled going 14-16 since the signing. After finishing the 2012 season with a solid 17-6 record, the 2008 World Series MVP went 8-14 in 2013 with a 3.60 ERA. Hamels eight wins in 2013 was the lowest output of his career, so the Phillies are definitely expecting a lot more from Hamels over the final five years of his contract. With the 33 starts he had in 2013, the Phillies were paying out $727,000 per appearance.

6 6 (tie). Cliff Lee, Philadelphia Phillies - $24 million per year

In December 2010, Cliff Lee had many suitors after his services with the Yankees and Rangers offering him very lucrative contracts. But ultimately Lee ended up taking a very generous offer from the Philadelphia Phillies for $120 million over five years, with an optional sixth year worth $27.5 million.

Since signing his lucrative contract, Lee has had two solid years and one forgettable one with 37 wins and 25 losses. In 2011 he went 17-8 finishing third in the NL Cy Young Award race, but followed that with a 6-9 record in 2012 before going 14-8 in 2013. The 2008 AL Cy Young Award winner has already made tentative plans to hang it up after his current contract runs out having told the media at the end of last season that he is "financially able to shut it down" and that he's also "getting up there in age." With the 35-year-old appearing in 31 games last year, he profited from just under $775,000 a start.

5 CC Sabathia, New York Yankees - $24.4 million per year

In 2009 when CC Sabathia decided to sign with the Yankees, his seven year $161 million contract was the highest total money ever dished out for a pitcher. Three seasons later at the conclusion of 2011 season, Sabathia negotiated a new and more profitable contract with the Yankees agreeing to a five-year deal worth $122 million. The new deal gave Sabathia a per year average of $24.4 million per year compared to the $23 million per year he was making previously.

Sabathia was rightly rewarded for his exceptional pitching, having compiled 59 wins and only 23 losses in his first three seasons as a Yankee, a .719 win-loss percentage, to go along with a 3.18 ERA. However, in the two years since the 33-year-old left-hander has seen a fairly significant drop-off going 29-19, a .604 win-loss percentage with a 4.08 ERA. Sabathia made 32 appearances in 2013 to make approximately $762,500 per start.

4 Zack Grienke, Los Angeles Dodgers - $24.5 million per year

The arms race for lucrative pitcher contracts started a couple months after the conclusion of the 2012 MLB season when the Los Angeles Dodgers signed Zack Grienke to what was then the biggest pitcher contract per annual basis. Grienke, who had just finished up a half-season stint with the Los Angeles Angels, moved across town to sign with the Dodgers for a six-year deal worth $147 million.

The 2009 AL Cy Young Award winner has proven solid thus far since signing with the Dodgers. Coming in with a 91-78 record after nine seasons in the big leagues, Grienke went 15-4 in 2013 with a 2.63 ERA and finished eighth in the NL Cy Young Award balloting. The recently turned 30-year-old made 28 appearances in 2013, meaning he averaged $875,000 per start.

3 Felix Hernandez, Seattle Mariners - $25 million per year

For one short month in February 2013, Felix Hernandez lived up to his nickname King Felix among starting pitchers when at the time he signed the most lucrative contract of any pitcher, worth $175 million over seven years. The Mariners made the investment on the young ace after he compiled a record of 59 wins and 50 losses between 2009 and 2012 for the listless Mariners.

It might seem suspicious to offer a pitcher big money with a career win-loss percentage of .561, but considering the Mariners have had two winning seasons in Hernandez's nine years and a win percentage of .449 during that time, there's good reason Seattle forked over some serious cash to the 2010 AL Cy Young Award winner. With the 27-year-old going 12-10 in 2013 with 31 appearances, Hernandez was banking a little over $800,000 per start.

2 Justin Verlander, Detroit Tigers - $25.7 million per year

A year and a half after one of the best pitching seasons in baseball history in 2011 when Justin Verlander won the AL Cy Young Award and AL MVP, the 30-year-old cashed in on the richest contract among all pitchers in baseball a week before the beginning of the 2013 season to surpass Hernandez. The deal he agreed to? A seven-year contract worth $180 million with an option for an eighth year worth $22 million in 2020 when he is 37-years-old.

Verlander for obvious reasons hasn't maintained his extraordinary pitching performance of 2011, but he has still been a solid asset for the Tigers, most recently leading them to the ALCS in 2013. He finished second in AL Cy Young Award voting in 2012 with a 17-8 record and followed that with a drop-off in production in 2013 going 13-12 with a 3.46 ERA. While Verlander has been a reliable pitcher having pitched at least 32 games for seven straight seasons, the Tigers will definitely want to see a better season from him going forward. After all, his contract is paying him over $750,000 per start based off his 34 appearances in 2013.

1 Clayton Kershaw, Los Angeles Dodgers - $30.7 million per year

Clayton Kershaw's seven year, $215 million contract is not only the highest average among all pitchers, it's now the highest annual average in all of the MLB at any position. The $30.7 million per year average is unprecedented for an MLB pitcher--surpassing the one-year salary of $28 million Roger Clemens made in 2007 for the New York Yankees--so it will be interesting to see if Kershaw can live up to the hype and expectation.

After coming off an NL Cy Young Award year where he had 16 wins and 9 losses along with a league-leading 1.83 ERA in 2013, the Dodgers better hope the 25-year-old left-hander only improves from there and produces at least 15+ wins a year. So far the former first-round pick has been nothing but solid in his young career, garnering a .626 win-loss percentage, which included a 21-win 2011 when he won his first NL Cy Young Award. Assuming Kershaw appears in 33 games in 2014 as he did in 2013, the Dodgers' ace will be making approximately $930,000 per start.

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