Big contract for any pitcher is risky business

The contract Japanese pitcher Masahiro Tanaka is going to receive is already giving some people upset stomachs. The size of it might end up being more eye-popping than the $50-60 million contracts teams gave to Yu Darvish and Daisuke Matsuzaka. Keep in mind that was before the posting fee was capped at $20 million. The Red Sox and Rangers each coughed up posting fees in excess of $50 million, making the total investment for each pitcher more than $100 million.

It was a big deal when Kevin Brown
became the first $100 million pitcher
in baseball when he signed with the Dodgers.

That big of an investment rarely works out well if you're expecting the player to pitch well over the life of the whole contract. Here are the biggest contracts ever given to pitchers:

Felix Hernandez, Mariners, $175,000,000 (2013-19)
CC Sabathia, Yankees, $161,000,000 (2009-15)
Zack Greinke, Dodgers, $147,000,000 (2013-18)
Cole Hamels, Phillies, $144,000,000 (2013-18)
Johan Santana, Mets, $137,500,000 (2008-13)
Matt Cain, Giants, $127,500,000 (2012-17)
Barry Zito, Giants, $126,000,000 (2007-13)
CC Sabathia, Yankees, $122,000,000 (2012-16)
Mike Hampton, Rockies, $121,000,000 (2001-08)
Cliff Lee, Phillies, $120,000,000 (2011-15)
Yu Darvish, Rangers, $111.700,000 (2012-2017)*
Kevin Brown, Dodgers, $105,000,000 (1999-2005)
Daisuke Matsuzaka, Red Sox, $102,111,111 (2007-2012)*
Adam Wainwright, Cardinals, $97,500,000 (2014-18)
Carlos Zambrano, Cubs, $91,500,000 (2008-12)
-Source: Cot's Baseball Contracts
*posting fee included with salary

Obviously most of these contracts are newer as teams have been flush with cash and the pay for elite pitchers has gone up. Though maybe it's interesting is that five of the top six contracts ever given out to pitchers weren't signed by free agents, but were extensions for guys with a year or two left before hitting the market.

Of the contracts that have been completed, all of them looked like a disaster at some point. Hampton's looked like one almost as soon as the ink dried in the thin Colorado air. Zito's was almost as bad save for the fact he still soaked up a lot of innings for the Giants over the course of his seven-year deal.

Over the course of Zambrano's extension, he suffered a decrease in either his performance or ability to take the mound each and every year of his new contract. Matsuzaka and Santana each had a few good years at the front ends of their deals before ineffectiveness and/or injuries did them in.

The best contract of all of them in my opinion was Brown's. Baseball's first $100 million arm was good for more than 1,000 innings with a 3.23 ERA over seven years. Brown, who I think has an underrated Hall of Fame case, missed some time with injuries, but still pitched a lot of mostly good innings for his money, only completely losing it the final year when he was 40.

The jury is still out on the other contracts. Cain, Verlander, Hamels and Sabathia each just endured their worst season in years. Greinke was very good, but missed time after breaking a bone in a scuffle with Carlos Quentin. With Hernandez, Lee, Darvish and Wainwright, things are looking so-far-so-good, though only Lee's contract is even close to completion.

The results here seem pretty apparent. If you don't have to spend almost $100 million or more on a pitcher, then don't. The risk is still one that teams are willing to make, especially teams that are close to contention. Should they be?

Possibly. In a way, this is already how teams view the cost of dabbling in free agency. They're willing to get a good value on the front end of a contract in exchange for dead money at the end.

Looking at each of these contracts, none of them really stopped the team paying the checks from doing anything else. Zito didn't keep the Giants from winning two World Series titles. Lee and Hamels aren't the problem with the Phillies' payroll. Even Mike Hampton's contract was eventually carved up and served in digestible bites that teams other than the Rockies helped swallow.

Unless Tanaka pulls a Hampton-Zito, the team that wins the bidding for his services will be getting a good pitcher for at least a few years. So any team with the money might as well bid away.