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The ideal Adam Wainwright extension

By Chris Cwik | CBSSports.com
Adam Wainwright wants to stay in St. Louis long-term. (US Presswire)

When one of the best pitchers in baseball wants to talk about a contract extension, you listen. Since he became a full-time starter, Adam Wainwright has been one of the game's most successful pitchers. Wainwright has expressed his interest to remain in St. Louis long-term, and things are trending in the right direction. Given his track record, there's a good chance Wainwright's next contract hits nine figures.

Few pitchers with Wainwright's service time have signed large extensions in recent season. The list is comprised of just four pitchers; Felix Hernandez, R.A. Dickey, Kyle Lohse and Johan Santana. Wainwright has been much better than Dickey and Lohse, so they don't fit as great comparisons. Talent-wise, Wainwright wasn't as great as either Hernandez or Santana early in their careers, and both signed their deals at earlier ages. Pitchers with six-to-eight years of service time rarely sign long-term extensions unless they are the once in a lifetime talent, or veterans looking for financial security after strong seasons. Wainwright is in neither category. Most pitchers with Wainwright's experience tend to hit the free-agent market.

First, a word of caution. Players who typically sign on the free-agent market make significantly more money than players who sign extensions. This is mainly due to the fact that multiple teams can drive up the bidding on a player in free agency. In the case of an extension, the player has less leverage, as he's only negotiating with one team. With that out of the way, the list of similar pitchers who signed free-agent deals is far more interesting.

NameIPK%BB%ERAFIPWARContract
John Lackey1501.018.90%6.90%3.813.8331.3$82.5 million over 5 years
Adam Wainwright1073.020.40%6.80%3.153.3122.9???
Cliff Lee1196.217.70%6.50%3.973.9822.9$120 million over 5 years
C.J. Wilson708.021.30%9.80%3.603.6814.1$77.5 million over 5 years
Ryan Dempster1218.118.50%11.60%4.824.5910.6$52 million over 4 years

The above chart shows players who signed extensions prior to their age-31 seasons, and their stats leading up to that point in their careers. CJ Wilson and Ryan Dempster aren't great comps for Wainwright, as both produced significantly less value than Wainwright at the same point in their respective careers. Both John Lackey and Cliff Lee, however, can provide some insight into what Wainwright could make in his extension.

Wainwright is probably looking for something better than Lackey's five-year, $82.5 million deal, and he's likely to get it. Lackey may have accumulated a higher WAR than Wainwright through age-30, but much of that is due to the different in innings pitched. It's a significant difference, but it's more a factor of Wainwright starting his career as a reliever and missing 2011 with Tommy John surgery. Health is a skill, and Lackey should receive a boost from staying healthy, but Wainwright has proven to be a better pitcher on a rate basis.

Lee is actually a great comp for Wainwright. Both players had an identical 22.9 WAR and a similar amount of innings pitched at the same point in their careers. On the free-agent market, that earned Lee a five-year, $120 million deal. This is the contract Wainwright's agent should be using in negotiations.

Given that Wainwright is signing an extension, his new contact may not reach the same heights. His agent could make the case that two seasons have passed, and inflation could push Wainwright's extension into Lee-territory. More than likely, he'll settle for an average annual salary between $21 million and $23.5 million. Though Wainwright could potentially make more money on the market next season, there's an advantage to signing his big deal now and staying in St. Louis. And since Wainwright has stressed his desire to remain a Cardinal, there's no reason this deal shouldn't get done before opening day.

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