The 30 Most Expensive Pitchers in MLB History: Were They Worth It?

Doug MeadCorrespondent IJanuary 23, 2012

The 30 Most Expensive Pitchers in MLB History: Were They Worth It?

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    Ever since Major League Baseball’s reserve clause was struck down in 1975 and pitcher Andy Messersmith signed a three-year, $1 million contract with the Atlanta Braves, free agency in baseball has thrived.

    With the birth of free agency, however, also came a much greater responsibility for general managers and owners across MLB, who were forced to add the role of speculator to their resumes. It became their task to properly financially assess the value of each player relative to their skills and what they could potentially bring to their new team.

    To say that some executives were better at that particular task than others would be a vast understatement. Throw into that the fact that smaller-market teams were forced to be much more budget-conscious, and the business of signing free agents literally became an exact science.

    Signing free-agent pitchers has always been a bone of contention, starting with the very first one, Messersmith. After signing with the Braves, Messersmith was 16-15 with his new team in two years, the second year interrupted by injuries.

    Messersmith was sold to the New York Yankees following the 1977 season, suffering through another injury-plagued season in the Bronx.

    If that first contract was any indication, signing free-agent pitchers certainly has a risk/reward factor that is practically impossible to gauge properly. However, it hasn’t stopped MLB executives from taking the risk anyway.

    The following is a list of the 30 most expensive pitching contracts in MLB history, with a somewhat educated opinion as to whether or not each pitcher lived up to that contract.


Honorable Mention, Pedro Martinez: Four Years, $53 Million

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    After winning the World Series with the Boston Red Sox in 2004 and becoming one of the most dominating pitchers in history, Pedro Martinez left the Red Sox and signed with the New York Mets for four years and $53 million.

    Was he worth it? No. Martinez enjoyed an excellent first season, with a 15-8 record and 2.82 ERA. However, during his last three seasons in New York, Pedro won only 17 games, dealing with lingering shoulder woes and eventually a torn rotator cuff, issues that prompted the Red Sox not to re-sign Pedro in the first place.

30. Randy Johnson: Four years, $52.5 million

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    When starting pitcher Randy Johnson joined the Arizona Diamondbacks prior to the 1999 season, he was joining a second-year franchise with hopes, but not much else. Johnson had already won one Cy Young Award, and was considered the premier left-handed pitcher in the American League at the time.

    Was he worth it? Yes. Yes. Yes. Four consecutive Cy Young awards and a World Series MVP absolutely makes this deal worthwhile. In fact, one could say he was actually underpaid.

    The overall value of the contract was $68.5 million, with the D-Backs picking up the option year on Johnson’s contract as well.

29. Darren Dreifort: Five years, $55 million

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    Aside from possibly two other pitchers on this list, it’s hard to look at the contract signed by Darren Dreifort and justify the merits of it in any good way.

    The Dodgers signed Dreifort to a five-year, $55 million contract in December 2000, after he had compiled a 39-45 career record with a 4.28 ERA in his first six seasons.

    Was he worth it? Absolutely and emphatically NO. Dreifort gathered a grand total of nine wins over the next four seasons, appearing as a middle-innings reliever in his final season.

28. Gil Meche: Five years, $55 million

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    You won’t find too many players that did what Kansas City Royals pitcher Gil Meche did in late January, 2011.

    Meche, who signed a five-year, $55 million contract before the 2007 season, retired from baseball rather than reporting to training camp and not earning his money.

    “When I signed my contract, my main goal was to earn it,” Meche said at the time. “Once I started to realize I wasn’t earning my money, I felt bad. I was making a crazy amount of money for not even pitching. Honestly, I didn’t feel like I deserved it. I didn’t want to have those feelings again.”

    Was he worth it? No. Meche put together two very good seasons for the Seattle Mariners prior to signing his deal with the Royals. Meche won 23 games in the first two years of his contract, however shoulder woes plagued him throughout 2009 and 2010, causing him to re-think things and walk away from the game and forfeit the final year of his deal.

    There is honor in baseball after all.

27. Mark Buehrle: Four years, $56 million

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    Before signing his deal with the Miami Marlins, Chicago White Sox pitcher Mark Buehrle completed a four-year, $56 million deal with White Sox. Winning an average of just under 14 games a season over 200 innings pitched each season and an ERA of 3.88 during the life of the contract, Buehrle also missed just one start over that period as well.

    Was he worth it? Yes. While the numbers posted during the four years aren’t totally overwhelming, Buehrle certainly didn’t fall under the weight of the deal.

26. Mark Buehrle: Four years, $58 million

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    The Miami Marlins set out to make a big splash, and they certainly provided it with the signings of Heath Bell, Jose Reyes and Mark Buehrle.

    Buehrle was signed to a four-year, $58 million contract after spending his first 12 seasons with the Chicago White Sox, winning 161 games.

    Was he worth it? Yes. Well, he will be if the Marlins win their third World Series title with him. Otherwise, look for Jeffrey Loria to unload Buehrle quickly if the Marlins fail to succeed next season.

25. Derek Lowe: Four years, $60 million

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    The Atlanta Braves have always regarded pitching as their primary weapon over the past 20 years, and that was evident with their fabulous run of 14 NL East titles in 15 seasons between 1991 and 2005.

    In January 2009, they sought to continue dominating with their starting rotation, signing free-agent pitcher Derek Lowe to a four-year, $60 million contract. Lowe was coming off a successful run with the Los Angeles Dodgers, posting a 54-48 record and 3.59 ERA in four seasons.

    Was he worth it? No. Giving a sizable contract to a pitcher in his mid-thirties is always risky (see Kevin Brown, LA Dodgers), and it certainly proved to be true with Lowe as well. After three seasons in Atlanta, Lowe was dealt to the Cleveland Indians along with cash, freeing up the rotation for younger stars Brandon Beachy, Mike Minor, Randall Delgado and Julio Teheran.

24. Chan Ho Park: Five years, $65 million

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    Boy, that guy Scott Boras is one shrewd agent.

    After nine years with the Los Angeles Dodgers, the last five as a somewhat effective starter, Chan Ho Park signed a five-year, $65 million contract with the Texas Rangers in late 2001.

    Park had posted an 84-58 record and 3.77 ERA during his time in LA, averaging 15 wins a season for his final five years in Dodger blue.

    Was he worth it? No. In three-plus years with the Rangers, Park won a grand total of 22 games, with an ERA of 5.79 along with a 1.61 WHIP. Without a doubt one of the worst pitcher contracts in MLB history.

23. Kevin Millwood: Five years, $60 million

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    Following his 2005 season with the Cleveland Indians in which he posted a 9-11 record and American League-leading 2.86 ERA, starting pitcher Kevin Millwood agreed to a four-year, $48 million contract with the Texas Rangers, with a vesting option for a fifth year.

    The Rangers are probably ruing the fact that Millwood did indeed vest in 2009, surpassing 180 innings to kick in his 2010 option.

    Was he worth it? No. Millwood was 48-46 with a 4.57 ERA in Texas, and they literally couldn’t wait to unload him, dealing him to the Baltimore Orioles in December 2009.

22. Roy Halladay: Three years, $60 million

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    In the deal that sent starting pitcher Roy Halladay from the Toronto Blue Jays to the Philadelphia Phillies in December 2009, the Phillies finalized a three-year, $60 million contract to finalize the transaction, with a vesting option for a fourth year that could bring the total value of the contract to $80 million.

    Was he worth it? Yes. Halladay won the Cy Young Award in 2010 and finished runner-up last season, and the 34-year-old right-hander shows absolutely no signs of slowing down whatsoever.

21. John Danks: Five years, $65 million

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    This offseason has certainly been puzzling when looking at the curious moves of the Chicago White Sox.

    Thus far, they have passed on retaining long-time starter Mark Buehrle, traded closer Sergio Santos, right fielder Carlos Quentin and reliever Jason Frasor and appeared to be in full-on rebuild mode.

    Then came the news that GM Kenny Williams signed starting pitcher John Danks to a five-year, $65 million contract extension, on the heels of several rumors regarding Danks’ availability.

    Was he worth it? Incomplete. This is probably the only player that I don’t have a definite feeling of “yes” or “no.” Danks is 26, has been durable and is a quality innings-eater. However, considering the moves the White Sox have made over the last two months, and considering the considerable discourse regarding Danks and Gavin Floyd’s availability, it’s certainly a curious move.

20. Josh Beckett: Four years, $68 million

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    When the Boston Red Sox announced the signing of free-agent starting pitcher John Lackey to a five-year, $82.5 million contract in December 2010, it appeared at the time that the Red Sox were sending a message to current pitcher Josh Beckett, indicating they might not be ready to commit long-term to Beckett.

    However, GM Theo Epstein quickly reached out to Beckett, indicating the exact opposite. Four months later, Beckett was signed to a four-year, $68 million salary, representing an average annual salary of $500,000 per year more than Lackey.

    Was he worth it? Yes. Based on the first year of Beckett’s salary, it’s hard to argue against justifying the salary. Beckett was 13-7 with a 2.89 ERA, 1.026 WHIP and just 6.8 hits given up per nine innings. While Beckett’s shoulder was considered problematic early in his Red Sox career, those concerns seem to have disappeared.

19. Roy Oswalt: Five years, $73 million

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    From the moment starting pitcher Roy Oswalt first stepped on the field for the Houston Astros in 2001, he was a model of consistency, never posting an ERA above 3.49 and posting back-to-back 20-win seasons in 2004 and 2005, winning the NLCS MVP Award in 2005 and posting five top-five finishes in Cy Young award balloting in his first six seasons.

    In August 2006, the Astros rewarded Oswalt with a five-year, $73 million contract extension, passing up the opportunity to become a free agent following the 2007 season.

    Was he worth it? No. In comparison with other top-tier pitchers, Oswalt was 61-46 with a 3.42 ERA during the life of the contract, missing two months of the 2011 season with recurring back issues.

18. Pedro Martinez: Six years, $75 million

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    Following his 1997 season during which he captured the National League Cy Young Award for the Montreal Expos with a 17-8 record, 1.90 ERA and 305 strikeouts, Pedro Martinez went to greener pastures, signing a six-year, $77.5 million contract shortly after the Expos traded him for Tony Armas and Carl Pavano.

    Was he worth it? Yes. Absolute no-brainer here. Pedro won two Cy Young Awards back-to-back in 1999 and 2000, finished in the top four in Cy Young Award voting four other times and finished his Red Sox career with a 117-37 record, the best winning percentage of any pitcher for any team in MLB history.

17. C.J. Wilson: Five years, $77.5 million

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    After helping to lead the Texas Rangers to back-to-back World Series appearances, left-handed starting pitcher C.J. Wilson decided to go back home, signing a five-year, $77.5 million contract with the Los Angeles Angels, returning to his Southern California roots.

    Wilson posted two strong seasons in the Rangers rotation after transitioning from the bullpen following the 2009 season.

    Was he worth it? Yes. This is obviously a judgment call here, considering Wilson just signed this deal less than two months ago. On paper, the contract gives the Angels one of the best starting rotations in the major leagues.

    However, can Wilson carry this success into his thirties? Considering that Wilson is moving into a more pitcher-friendly environment, the guess is yes.

16. Felix Hernandez: Five years, $78 million

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    Following an outstanding 2009 season, the Seattle Mariners wrapped up their star pitcher, Felix Hernandez, signing him to a five-year, $78 million contract in January 2010.

    Hernandez finished second in Cy Young Award balloting after posting a 19-5 record and 2.49 ERA.

    Was he worth it? Yes. So, what did Hernandez do after finishing second in Cy Young Award balloting and signing a nice, fat contract? He won the award the following season. Hernandez continues to put up stellar numbers despite an anemic offense that can’t support him with enough runs.

15. Justin Verlander: Five years, $79.5 million

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    When the Detroit Tigers inked star right-handed pitcher Justin Verlander to a five-year, $80 million deal in February 2010, they certainly hoped that Verlander would continue on a path of positive development after posting a 19-9 record and 3.45 ERA in 2009.

    Verlander indeed was good the following year, but in 2011, he put together a season that will ultimately go down as one of the best single-season pitching performances in MLB history.

    Verlander led just about major pitching category, including the triple crown of pitching, posting a 24-5 record, 2.40 ERA, 250 strikeouts, 0.92 WHIP, 6.2 hits per nine innings and and ERA+ of 170. Verlander became the first starting pitcher to capture both the Cy Young and MVP award since Roger Clemens in 1986.

    Was he worth it? Yes. At just 28 years of age, Verlander figures to continue dominating in the American League for several years to come.

14. A.J. Burnett: Five years, $82.5 million

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    For some inane reason, players oftentimes are rewarded lofty long-term contracts based on what appears to be one good season. Such is the case with New York Yankees pitcher A.J. Burnett.

    After winning 18 games with the Toronto Blue Jays in 2008, the Yankees rewarded Burnett with a five-year, $82.5 million contract. Burnett was given ace money even though he was only the second-best pitcher for the Blue Jays (Roy Halladay).

    Was he worth it? No. Burnett hasn’t even come close to posting the same kind of numbers in New York, with an ERA north of 5.00 ERA the past two seasons. The Yankees brought in Michael Pineda and Hiroki Kuroda in recent weeks to bolster the staff, and while Burnett could have been given a wake-up call with the recent transactions, it’s doubtful that anyone will ever think that his contract was justified.

13. John Lackey: Five years, $82.5 million

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    Following the 2009 season, the Boston Red Sox wisely decided to let outfielder Jason Bay walk, opting not to offer Bay a five-year contract.

    They should have done the same with pitcher John Lackey.

    Following an eight-year career with Los Angeles Angels in which Lackey compiled a 102-71 record and 3.81 ERA, including winning the seventh game of the 2002 World Series, Lackey signed a five-year, $82.5 million contract with the Red Sox, using New York Yankees pitcher A.J. Burnett’s similar contract as a benchmark.

    Was he worth it? No. Lackey was a pedestrian 14-11 with a 4.40 ERA in his first season, and followed that up with a 12-12 record and 6.41 ERA last season, not to mention a surly attitude and alleged chicken wing-eating, beer-drinking clubhouse antics.

12. Jered Weaver: Five years, $85 million

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    Last September, the Los Angeles Angels announced that they had signed ace right-hander Jered Weaver to a five-year, $85 million contract, ensuring that Weaver would not test the waters of free agency and keeping him in the place that he loves.

    Weaver has been outstanding ever since debuting with the Angels back in 2006, posting a career record of 82-47 and 3.31 ERA. Weaver’s 2.41 ERA in 2011 was just 0.01 behind AL MVP and Cy Young Award winner Justin Verlander, and Weaver also placed runner-up to Verlander in Cy Young Award balloting as well.

    Was he worth it? Yes. Weaver could have easily signed for more money had he opted for free agency, however he instructed agent Scott Boras to get a deal done with the Angels, choosing home over money.

    "If $85 (million) is not enough to take care of my family and other generations of families then I'm pretty stupid, but how much money do you really need in life?" Weaver said at the time. "I've never played this game for the money. I played it for the love and the competitive part of it. It just so happens that baseball's going to be taking care of me for the rest of my life."

11. Mike Mussina: Six years, $88.5 million

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    Many fans in Baltimore were saddened by the departure of long-time Orioles starting pitcher Mike Mussina, who amassed a 147-81 record and 3.53 lifetime ERA during his 10 years there. Many consider Mussina to be the second-greatest pitcher in Orioles history, behind Hall of Famer Jim Palmer.

    The New York Yankees came calling at the end of the 2000 season, wooing Mussina with a six-year, $88.5 million contract.

    Was he worth it? Yes. Mussina’s numbers in his first six years with the Yankees (92-53 record, 3.80 ERA) were similar to the numbers posted in Baltimore. While the Yankees were unable to win a World Series championship during Mussina’s tenure, he nonetheless helped lead them to six straight postseason berths, posting a 3.80 ERA in 15 postseason starts over the life of the contract.

10. Carlos Zambrano: Five years, $91.5 million

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    On the heels of two successive seasons in which Chicago Cubs right-hander Carlos Zambrano placed in the top five in NL Cy Young Award balloting, the Cubs rewarded him with a five-year, $91.5 million contract  extension in August 2007.

    At the time, Zambrano was happy with Chicago, and the Cubs were happy with Zambrano.

    "Not everything is about money, you know," Zambrano said at the time. "I know if I got to free agency there were a lot of things that would come to me and offer me. I feel comfortable here. I feel good here and my family feels good here."

    Everyone may have felt good at the time, but that rapidly deteriorated.

    Was he worth it? No. Zambrano did follow up with a nice season in 2008, with a 14-6 record and 3.91 ERA. However, his over-emotional temperament and battles with teammates eventually and finally spelled doom for Zambrano, who was dealt to the Miami Marlins in early January. The Cubs gladly ate $15 million of Zambrano’s salary for the 2012 season just to be rid of the mercurial nuisance.

9. Daisuke Matsuzaka: Six years, $103 million

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    Prior to the record signing of Yu Darvish by the Texas Rangers, the Boston Red Sox posted a then-record $51.1 million in November 2006 to the Seibu Lions of Japan’s Pacific League to exclusively negotiate with star pitcher Daisuke Matsuzaka.

    Matsuzaka was then signed to a six-year, $52 million contract, making the contract worth $103 million, the second-highest amount of money ever paid for a right-handed pitcher (Kevin Brown).

    Was he worth it? No. It appeared after two seasons that Dice-K was on his way to stardom, winning 33 games, including an 18-3 record and 2.90 ERA in 2008. However, over the past three seasons, Matsuzaka has won a grand total of 13 games, battling a succession of injuries along the way, including elbow issues which led to Tommy John surgery in June.

    Matsuzaka expects to ready by the All-Star break in 2012, however, unless he comes back, wins every start and takes the Red Sox to the World Series, there is no way this contract is worth it.

8. Kevin Brown: Seven years, $105 million

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    On Dec. 12, 1998, the Los Angeles Dodgers signed right-handed starting pitcher Kevin Brown to a seven-year, $105 million contract, the first $100 million contract ever given to a player in MLB history.

    Brown, who had put together three outstanding seasons with the Florida Marlins and San Diego Padres just prior to signing his record contract, was 33 years old at the time, and many questioned the wisdom of giving such a large sum of money to a player already in his mid-thirties.

    Was he worth it? No. An emphatic no, that is. While the numbers may look decent for Brown in his five seasons with the Dodgers (58-32, 2.83 ERA), it was nowhere near what was expected of Brown, who was paid ace money to help the Dodgers get to the postseason, which he failed to do.

7. Yu Darvish: Six years, $111.7 million

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    Between posting $51.7 million and then agreeing on a six-year, $60 million deal, the Texas Rangers made the contract of Japanese pitching Yu Darvish the most expensive deal ever for a right-handed pitcher in the history of Major League Baseball.

    That’s pretty heady stuff, considering the 25-year-old has never pitched one inning in the majors. However, the Rangers were comfortable enough with Darvish, after following him for over two years, to commit the record money.

    Was he worth it? Yes. I’m going out on a limb here, I know. However, Darvish wasn’t valuable just to the Rangers. Every single scout and MLB executive who has had the opportunity to watch Darvish in person has walked away more than impressed.

6. Mike Hampton: Eight years, $121 million

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    In 1999 and 2000, left-hander Mike Hampton put together two excellent seasons, finishing runner-up in the National League Cy Young Award balloting in 1999 with the Houston Astros (22-4, 2.90 ERA) and helping the New York Mets reach the World Series the following season (15-10, 3.14).

    When it came time to get paid for his excellence, the Colorado Rockies came knocking, offering Hampton an eight-year, $121 million contract, which he happily accepted. However, the Rockies clearly rued that decision, as Hampton’s career with the Rockies ended after two miserable seasons (21-28, 5.75 ERA).

    The Rockies unloaded Hampton following the 2002 season to the Florida Marlins, who immediately dealt him to the Atlanta Braves two days later.

    Was he worth it? No. Hampton won a total of 56 games in those eight years, three wins less than CC Sabathia’s total in the first three years of his record contract.

5. CC Sabathia: Five years, $122 million

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    After previously signing the most expensive contract for a pitcher in MLB history, New York Yankees pitcher CC Sabathia was smart enough (rather, his agent was) to include an opt-out clause that allowed him to walk away from the deal after three seasons, presumably to sign an even fatter contract.

    This past October, Sabathia and the Yankees decided that the opt-out clause wasn’t necessary, getting together at the 11th hour to renegotiate his deal for five years and $122 million. The new deal essentially added one year and an extra $30 million for Sabathia.

    Was he worth it? Yes. Sabathia has done nothing but win in the Bronx, and is still the unquestioned ace of the Yankees staff. If Sabathia can stay in relatively good shape, there’s no reason to think that he can’t continue leading the Yankees into the postseason for the foreseeable future.

4. Barry Zito: Seven years, $126 million

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    There should be no question in anyone’s mind that this particular contract turned out to be one of the worst decisions in MLB history.

    After a brilliant seven-year career with the Oakland Athletics that netted a Cy Young Award in 2002, left-hander Barry Zito signed a seven-year, $126 million contract with the San Francisco Giants following the 2006 season. In his first five seasons across the bay, Zito has yet to post a winning record in any one season, and was left off the roster for the entire postseason in 2010 as the Giants captured their first World Series championship in 56 years.

    Was he worth it? No. Absolute no-brainer with this one, and the Giants are still on the hook for an additional $46 million.

3. Cliff Lee: Six years, $147.5 million

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    When thinking about the career of Philadelphia Phillies starting pitcher Cliff Lee, the hit Beatles song "The Long and Winding Road" comes to mind.

    Lee showed flashes of brilliance early in his career with the Cleveland Indians, but inconsistency plagued him early on. In 2008, Lee clearly figured things out, winning the AL Cy Young Award with a spectacular 22-3 record and 2.54 ERA.

    Over the next two seasons, Lee was traded three times, yet still managed to put up terrific numbers, finally settling back in Philadelphia in December 2010 armed with a five-year, $120 million contract, with a vesting option for the 2016 season that could make the contract worth $147.5 million.

    Was he worth it? Yes. One has to think yes at this point, even though Lee has only worked through one year of the contract. His 17-8 record and 2.40 ERA earned him a third-place finish in NL Cy Young Award balloting, and there’s no reason to think that Lee is going to slow down anytime soon.

2. Johan Santana: Six years, $143 million

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    In a four-year period between 2004 and 2007, there was no better left-handed pitcher in MLB than Minnesota Twins starting pitcher Johan Santana. Santana won the Cy Young Award in both ’04 and ’06, and finished in the top five in Cy Young Award balloting the other two years.

    When it came time to get paid for his considerable services, the smaller-market Twins were virtually out of the running from the start. However, the New York Mets had no problem whatsoever in ponying up huge dollars for Santana, offering him a six-year, $137.5 million contract with a club option for the 2014 season with a $5.5 million buyout that could make the contract worth about $150 million over seven seasons.

    Was he worth it? No. Santana was terrific his first year with the Mets, winning the National League ERA title and finishing third in Cy Young Award balloting. However, the problems began the following season, with Santana missing several starts in 2009 and getting shut down in early September 2010 with shoulder issues that sidelined him for the entire 2011 season.

    Setbacks from his left shoulder surgery delayed Santana’s return, and lingering concerns remain as to whether or not Santana will be healthy enough to pitch at all in 2012.

1. CC Sabathia: Seven years, $166 million

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    When the New York Yankees finished out of the playoffs following the 2008 season, GM Brian Cashman decided to go to work and earn his money.

    Cashman signed former Cy Young Award winner CC Sabathia to a record seven-year, $161 million contract, instantly putting the Yankees back in the forefront. Signing Sabathia wasn’t the only move made during the offseason—Cashman also inked A.J. Burnett to a five-year, $82.5 million deal and first baseman Mark Teixeira to an eight-year, $180 million.

    All in a day’s work in the Bronx.

    Was he worth it? Yes. Sabathia won 59 games in the first three years of his mega-deal before ripping it up and signing a new contract in late October. And the spending spree that Cashman embarked on led to the Yankees winning their 27th World Series championship.


    Doug Mead is a featured columnist with Bleacher Report. His work has been featured on the Seattle Post-Intelligencer, SF Gate, CBS Sports, the Los Angeles Times and the Houston Chronicle. Follow Doug on Twitter, @Sports_A_Holic.