Cole Hamels should be smiling for the next six years with the Phillies.
The $144 million is the second-richest contract ever given to a pitcher, trailing only the $161 million deal CC Sabathia received from the New York Yankees in 2009. Hamels also became the eighth pitcher in baseball history to sign a contract worth at least $100 million in total value.
But a big $100 million contract doesn't guarantee 20-win seasons, Cy Young Awards and World Series championships for the teams that hand out those deals. In a few instances, those agreements backfired spectacularly.
The $100 million seal was broken in 1999 when the Los Angeles Dodgers signed Kevin Brown. Let's take a look at his contract and the seven other $100 million deals that have been awarded to pitchers since then. How did they end up working out and which turned out to be the best value?
Kevin Brown was the first pitcher to get a $100 million contract when he signed a seven-year deal worth $105 million with the Los Angeles Dodgers before the 1999 season.
Before signing with the Dodgers, Brown had one 20-win season, going 21-11 for the Rangers in 1992. He earned four All-Star appearances and was the runner-up for the 1996 AL Cy Young Award.
Brown won a World Series championship in 1997 with the Florida Marlins. He returned to the World Series the following season after being traded to the San Diego Padres. The Padres ended up losing to the New York Yankees.
Did the Dodgers get their money's worth? Brown compiled a 58-32 record and 2.83 ERA in five seasons while struggling with frequent elbow and back injuries. The Dodgers never finished in first place with him.
They ended up unloading Brown to the Yankees in 2004. During his two years in pinstripes, he finished with a 14-13 record and 4.95 ERA. The Yankees lost in the playoffs in both of those seasons.
Mike Hampton was the second pitcher to break the $100 million barrier, signing an eight-year, $121 million contract with the Colorado Rockies before the 2001 season.
In 1999, Hampton went 22-4 with the Astros for his one 20-win season. He also made his first All-Star team that year and finished second in the NL Cy Young Award vote.
The Mets traded for Hampton in 2000. He went 15-10 with a 3.14 ERA, helping the Mets to a wild-card playoff spot and a run to the World Series. The Mets lost the championship to the Yankees.
Hampton's stint with the Rockies was disastrous. As ESPN's Tim Kurkjian explained in 2002, the left-hander lost his release point, and the thinner air in Denver adversely affected his sinker.
After going 21-28 with a 5.75 ERA in two seasons, the Rockies traded him to the Atlanta Braves, eating a sizable portion of that contract in the process.
The Braves got the best part of the deal. Hampton went 35-24 with a 4.10 ERA in four seasons with Atlanta, helping win three division titles.
Mike Hampton's tenure with the Rockies was bad, but with Barry Zito and the San Francisco Giants, we may have the worst free-agent agreement of all time.
Zito signed a seven-year, $126 million deal with the Giants before the 2007 season, the biggest contract ever given to a pitcher at the time.
Prior to the deal, Zito compiled a 102-63 record with the Oakland Athletics. He had one 20-win season in Oakland, going 22-5 in 2002—a performance that earned him the AL Cy Young Award. Zito was also named to three All-Star teams during his tenure with the A's.
Nothing even close to that success and prosperity has taken place during Zito's six seasons with the Giants. During that time, he's put together a 51-67 record and 4.45 ERA. He was famously held off the Giants' postseason roster in 2010 when the team went on to win the World Series.
Zito can't really put that championship on his resume, can he? But presumably, he can say he contributed to a division-winning team that season.
In his sixth year with the Giants, Zito may be putting together his best season. In 19 starts, he's racked up an 8-6 record and 3.75 ERA for a team that currently holds first place in the NL West and appears to be headed to the postseason. Maybe this time Zito will get to pitch in the playoffs.
Santana agreed to a six-year, $137.5 million deal, which was the richest deal ever given to a pitcher at the time, surpassing Barry Zito's contract with the Giants.
When he joined the Mets, Santana was 28 years old and had pitched eight seasons in the big leagues. He had a 93-44 record with the Twins, helping to win four division titles.
From 2004-06, he was the best pitcher in baseball, racking up one 20-win season and winning 19 games two years later. Those performances earned him two AL Cy Young Awards.
Santana hasn't pitched at that level with the Mets, but he's been an ace starter in his three seasons in Queens. He's compiled a 46-32 record with a 3.03 ERA. In his first season with the Mets, Santana went 16-7 and led the majors with a 2.53 ERA.
Shoulder surgery forced Santana to miss the entire 2011 season. But since returning, he's been a top pitcher for the Mets. His signature moment with the team came on June 1, when he pitched the first no-hitter in franchise history.
Santana has one more season and a club option worth a total of $50.5 million remaining on his contract. Will the Mets get their money's worth?
Consider that starting pitching allowed the Mets to contend for a playoff spot until recently. Santana was obviously a big part of that. Is it a coincidence that the Mets fell out of the race as Santana had to go on the disabled list with an ankle injury?
The New York Yankees needed an ace starting pitcher to return to championship glory. General manager Brian Cashman (and owner George Steinbrenner, surely) had eyes on CC Sabathia, envisioning the left-hander as the man to get them back to the World Series.
Sabathia signed a five-year, $122 million contract prior to the 2009 season.
Before joining the Yankees, Sabathia compiled a 117-73 record with the Cleveland Indians and Milwaukee Brewers. He didn't put together a 20-win season with the Tribe, but was named to three All-Star teams and won the AL Cy Young Award in 2007. He also finished second in AL Rookie of the Year voting in 2001.
Sabathia was part of two division championships in Cleveland. But he may have shown how valuable he could be to a team after getting traded to the Brewers in 2008. He went 11-2 with a 1.65 ERA, leading Milwaukee to the postseason for the first time since 1982.
Since signing with the Yankees, Sabathia has been one of the best pitchers in baseball. In his first three seasons in the Bronx, he won 59 games, earning his first 20-win season (21-7) in 2010. The Yankees have been to the postseason three times and won the World Series in 2009.
Exercising an opt-out clause in his contract, Sabathia signed a one-year, $25 million extension for 2016 and has a $25 million vesting option for 2017. That brought the total value of Sabathia's contract to $161 million over seven years—the richest contract ever awarded to a pitcher.
Yes, Sabathia is the highest-paid pitcher in baseball. And they haven't competed for championships just because of him. But as loaded as the Yankees' roster is with superstars, they can't get far without Sabathia as the No. 1 man in their rotation.
Cliff Lee was a man in demand after becoming a free agent following the 2010 season. He ended up shocking baseball by agreeing to a five-year, $120 million contract, spurning the Yankees and Texas Rangers to return to the Philadelphia Phillies, with whom he pitched in his first World Series.
Lee was 32 years old at the time he signed his deal with the Phillies, having pitched seven full major league seasons.
During stints with the Indians, Phillies, Mariners and Rangers, Lee put together a 102-61 record. He had one 20-win season, going 22-3 with an AL-leading 2.54 ERA in 2008. That performance earned him an All-Star appearance and the AL Cy Young Award.
Lee was traded to the Phillies after that season, going 7-4 with a 3.39 ERA and giving Philadelphia the push it needed for its second consecutive World Series appearance. The Phillies ended up losing to the New York Yankees.
However, Lee was back in the World Series again the following season after taking an unusual route to get there.
The Phillies traded him to the Mariners. Seattle was awful in 2010 and became sellers at the trade deadline. They dealt him to the Rangers, who needed an ace to boost their postseason chances.
Since reuniting with the Phillies, Lee has gone 18-14 with a 3.25 ERA. He was outstanding in his first season back with Philadelphia, compiling a 17-8 record and 2.40 ERA and helping the Phillies to a fifth consecutive NL East division title.
Lee has struggled this season, going 1-6 with a 3.95 ERA. Initially, he was victimized by poor run support. But as the season has progressed, Lee just hasn't pitched very well.
There have been rumors the Phillies might trade him, but with the re-signing of Hamels, Lee will likely be a part of the core of a starting rotation that should enable the Phillies to compete again next year.
The San Francisco Giants didn't want to go into the 2012 season with Matt Cain's contract situation unresolved. Cain didn't want to begin the season without agreeing to an extension.
So the two sides eventually agreed on a six-year, $127.5 million deal that ended up causing ripples throughout baseball.
Would Hamels have gotten his big contract without Cain raising the bar? Would Zack Greinke have already re-signed with the Brewers if "Matt Cain money" wasn't the goal on the free-agent market?
Cain was 27 years old when he signed his contract, having pitched six full big league seasons for the Giants.
His record during those six seasons was an unimpressive 69-73, but the Giants understood that Cain suffered from poor run support during his career in San Francisco. All the team had to do was look at the 2011 season, during which Cain finished 12-11 despite a 2.88 ERA.
Cain hasn't had a 20-win season with the Giants, but he's been a three-time All-Star (including this year) and was a major factor in the team's NL West title and World Series championship in 2010.
If you want to know how good Cain is, look at that 2010 postseason, during which he didn't allow an earned run in three starts totaling 21.1 innings.
Thus far in 2012, Cain has a 10-3 record and 2.74 ERA. He's been one of the best pitchers in baseball, leading the NL with an 0.95 WHIP (walks and hits per innings pitched) and holding opposing batters to a .208 average—the second-best mark in baseball.
This could very well earn Cain his first Cy Young Award this season.
That brings us to baseball's newest $100 million pitcher, the reason this slideshow was put together.
Cole Hamels re-signing with the Phillies was somewhat of a surprise, given that he was two months from free agency and expressed interest in seeing what his worth would be on the open market. Also lurking with money ready to spend were the Dodgers, who would allow Hamels an opportunity to return to his southern California roots.
Hamels is at the point of his career where his fellow $100 million pitchers were when they signed their lucrative contracts. He's 28 years old with seven major league seasons on his resume.
During those seven years with the Phillies, Hamels has compiled an 85-58 record. He hasn't put together a 20-win season, though there's a strong chance he could achieve that this year with an 11-4 record thus far. Hamels' first Cy Young Award is also a possibility this season, as his numbers put him among the top pitchers in the NL.
Hamels has been a key part of an impressive five-year run for the Phillies. Philadelphia has won five consecutive division titles, made it to two World Series and won a championship in 2008. Hamels was the MVP of that 2008 World Series, compiling a 2.77 ERA in two starts.
Is Hamels the second-best pitcher in baseball, as his contract status now implies? No, but these sorts of things are all about the timing. Hamels' contract was up at a time that's never been better for starting pitchers.
Additionally, the Phillies needed to keep him to stay competitive and reload for another championship run. Though Roy Halladay and Cliff Lee are also in Philadelphia's starting rotation, Hamels could end up being the ace of the staff next season. He'll certainly be paid like the No. 1 guy.
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