Could Zack Greinke Contract Make Clayton Kershaw MLB's First $200M Pitcher?

Ian Casselberry@iancassMLB Lead WriterNovember 29, 2012

Zack Greinke could become MLB's highest-paid pitcher.
Zack Greinke could become MLB's highest-paid pitcher.Lisa Blumenfeld/Getty Images

If the Los Angeles Dodgers end up signing free-agent pitcher Zack Greinke, the transaction will obviously cost the team a whole lot of money.

Greinke is reportedly seeking a six-year, $150 million contract. With the bidding war between the Dodgers and the Los Angeles Angels—who would very much like to keep Greinke—it's possible that Greinke's eventual deal could exceed those numbers. 

ESPN's Buster Olney talked to a source involved in negotiations with Greinke who speculated that the package could ultimately exceed the seven-year, $161.1 million contract that CC Sabathia signed with the New York Yankees in 2009, which happens to be the biggest contract a pitcher has ever received. 

But if the Dodgers do eventually win the auction for Greinke, that deal could end up costing the team even more down the line. Incumbent ace Clayton Kershaw is set to become a free agent after the 2013 season. If Greinke is worth more than $160 million, could Kershaw hit the $200 million mark with his next contract?

Let's start with the obvious reason Kershaw will get a richer contract than Greinke: He's a better pitcher.

(Actually, the truly most obvious reason Kershaw's deal will be bigger is because he'll become a free agent a year after Greinke did. As much as these sorts of things are about talent, they are also about timing. When you become a free agent is awfully important.) 

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The 25-year-old left-hander is coming off two consecutive seasons in which he led the National League in ERA and WHIP (walks and hits per innings pitched). He also led the league in strikeouts last season and finished one away from the top in 2012.

I would argue (and have done so, in writing) that Kershaw should also have won two straight NL Cy Young Awards, rather than winning in 2011 and finishing second this year.

That's not to say Greinke also hasn't been excellent. He has an AL Cy Young Award on his mantle, having won the honor in 2009 with a 2.16 ERA and 16-8 record. 

During his past two seasons, Greinke has twice reached 200 strikeouts, and his win-loss record is 31-11 with a 3.66 ERA. In 2011, he led MLB with a rate of 10.5 strikeouts per nine innings. 

If the Dodgers sign Greinke, the expectation for him will be to pitch as well as Kershaw has over the last two years. But Kershaw already is the most dominant pitcher in the NL. 

Another reason that Kershaw will ultimately fetch an even larger contract than Greinke is because he throws a baseball with his left hand. Cot's Contracts lists MLB's richest contracts by total value and average annual value, and nearly all of the pitchers that top those lists are all southpaws.

Sabathia, of course, leads the way. Cole Hamels is in the club after signing his six-year, $144 million contract extension with the Philadelphia Phillies this year. Johan Santana is next on the list. Barry Zito and Cliff Lee are close behind. 

The one right-hander that breaks through the cluster of lefties on those lists is Matt Cain, whose six-year, $127.5 million contract extension with the San Francisco Giants set the bar that Greinke is currently trying to clear. 

So righties get plenty of love too. (Roger Clemens actually has the largest one-year salary in MLB history at $28 million. But Greinke probably isn't going to surpass that figure.) It's just that Greinke's reign at the top of the heap is probably only going to last one year.

The mind boggles at what the bidding could reach for Kershaw next winter if he hits free agency. Yet the likelihood of the Dodgers even letting it get to that point seems pretty low.

Most everyone expects the Dodgers to blow away the competition with an offer for Greinke. The same would surely hold true with Kershaw next year. And since the Dodgers already have Kershaw, their megabucks ownership is not going to let him get away. 

Sabathia established the upper reaches of contract length for pitchers by getting a seven-year deal from the Yankees. So that's probably what Kershaw will aim for. That's probably also how he'll get to the $200 million benchmark, if that's the ultimate goal. 

An eight-year, $200 million contract would give Kershaw an average annual salary of $25 million. That's presumably the mark that Greinke is looking to hit with his contract, which would nudge him just above Sabathia's $24.4 million average yearly paycheck. Hamels and Lee are in the $24 million club too. 

So $25 million is the hurdle for Kershaw to clear with his next contract. A seven-year, $200 million package works out to $28.6 million per season. There it is. Kershaw would be the top dog among MLB pitchers both in terms of total contract value and average yearly salary. 

Perhaps even more impressive is that Kershaw will be only 25 years old by the end of the 2013 season. That's four years younger than Greinke is now. He'll be three years younger than Sabathia and Hamels were when they signed their contracts, and six years younger than Lee was. 

That could mean Kershaw signs a deal longer than seven years. But what's more likely is that he'll go for another contract when he's just 32 years old. Who knows what kind of pitcher Kershaw will be by then, but there's no reason to think he won't still be extremely effective, barring unforeseen circumstances.

We also have to go back to the fact that Kershaw is left-handed. He'll absolutely find work if he wants it. 

But the first thing Kershaw might do with that left hand when he reports to the Dodgers spring training camp in Glendale, Ariz., in February is shake Greinke's hand (presuming the two are teammates, of course).

Someone had to set the market that Kershaw will eventually shatter.

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