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The precedent for a Jon Lester extension

Jon Lester will become one of the highest paid pitchers in baseball when he signs his next contract. History, however, suggests that signing the lefty to a long-term contract may not be the most prudent thing to do.


Jon Lester is going to get paid. That much is already settled. In his ninth major league season, Lester is having his best year, posting a 2.65 ERA, 2.61 FIP (fielding independent pitching), 134 strikeouts and 29 walks. At the age of 30, Lester is set up to get a major payday in his next contract in terms of both money and contract length.

Whether or not the Red Sox will dole out the dollars that the lefty demands is still up for debate. Jon Heyman of CBS Sports recently wrote that Lester will likely get a contract in the range of $125 million and $189 million as a free agent, suggesting the Cole Hamels and Zack Greinke contracts as good references.

Considering the cost of elite starting pitching on the free agent market, Lester's potential take home as a free agent is not ridiculous. While the demands may not be out of this world, the potential ramifications of such a long-term deal for a pitcher are significant for an organization. Recent long-term contracts have shown the risks of committing that kind of money to a pitcher.

Among the recent long-term contracts given out to a pitcher is the deal the Yankees signed CC Sabathia to in 2009, which was extended in 2011 to add an additional year to his seven-year deal and another $25 million. With his current contract, Sabathia is signed through the 2016 season. Through the first four years, Sabathia posted numbers in line with some of the top pitchers: Sabathia had a 3.22 ERA, 3.28 FIP, and a 3.3 strikeout-to-walk ratio.

The last two years, however, have not been as sweet for Sabathia. Sabathia turned in the worst season of his career in 2013, posting a 4.78 ERA, 4.10 FIP, and a 2.7 strikeout-to-walk ratio. The 33-year-old's struggles have only been magnified in 2014, when he's started just eight games and his season likely done with knee troubles. Microfracture surgery is not out of the question and some have speculated that the injury could be career ending.

There are a couple of important things to consider with the Sabathia. When he signed the contract, Sabathia was 28-years-old with no injury history. The lefty was one of the most durable and dominant pitchers in baseball for an lengthy period of time, covering multiple organizations. The contract was viewed in many eyes as one that would most definitely pay off in the short term (and it did with a World Series title). The risk in a contract inherently increases as any pitcher ages out of their prime.

20140510_ads_bs5_075.jpg.0Photo credit: Benny Sieu-USA TODAY Sports

For Sabathia, the production fell off a cliff and might now be over with money still left on the contract. While the contract will likely still be viewed as a success because of the World Series title that Sabathia helped lead the team to a World Series, the long-term deal could still financially burden the team in the years to come.

A pitcher who signed a long-term deal that flopped was someone who the Red Sox nearly traded Lester for: Johan Santana. Santana was traded to the New York Mets at the age of 29 after establishing himself as the best pitcher in baseball, claiming two Cy Young awards during his time with the Minnesota Twins. With the Twins, Santana has a 3.22 ERA, 3.31 FIP, and a 3.8 strikeout-to-walk ratio.

When he was traded to the Mets, Santana signed a six-year, $137.5 million contract with the Mets. While Santana performed well with the Mets when he was on the field, the lefty missed a lot of time due to injury. Santana missed all of the 2011 and 2013 season after he tore his shoulder capsule twice. Santana missed his age 32 and 34 season and dealt with injuries despite not having any prior injury history with the Twins.

Some long-term contracts, however, don't have the fate of Sabathia and Santana's deals.

One such contract is the five-year, $120 million contract that Cliff Lee signed with the Phillies before the 2011 season. Lee, who was 32 when he signed the contract, has been nothing but excellent with the Phillies. In his second tenure with the team, Lee has posted a 2.83 ERA, 2.83 FIP, a 6.6 strikeout-to-walk ratio. Lee has not had any many injuries and has consistently been one of the top pitchers in baseball, despite his age.

Lee, however, represents the exception rather than the rule. Among the many pitchers who flamed out after signing a long-term contracts are Barry Zito and Mike Hampton. Pitchers who have not been the same include Justin Verlander and Matt Cain. The jury is still out on pitchers such as Zack Greinke, Cole Hamels and Masahiro Tanaka, among others.

Some team will be willing to give Jon Lester a long-term contract. Precedent shows that giving a long-term contract may not be the prudent thing for a team to do. While Lester will certainly provide value to the Red Sox in the immediate years following a new contract, whether or not the 30-year-old stays healthy is absolutely up in the air. Pitchers such as Sabathia and Santana had no injury history prior to signing their new contracts. While Lester has not had any injury history, that is not a guarantee in the future, given the Tommy John epidemic and the use of pitchers in baseball today.

While Jon Lester will set up the Lester family for generations to come with his upcoming contract, whether or not the Red Sox should be the team to sign him is very much worth debating.