A Look at Potential $100 Million RHP Contracts
Here's the debut from another new Beyond the Box Score family member, Joshua Worn. He runs Walkoff Woodward, the ESPN Sweetspot Blog dedicated to the Detroit Tigers. Please welcome him with open arms! -jbopp
The other day Ken Rosenthal penned a column regarding Matt Cain and the inevitable pay day he’ll see, if not as an extension from the Giants, then as a Free Agent once the 2012 season ends. Rosenthal focused on how Cain deserves to be the first right handed pitcher to sign a $100 million contract since Kevin Brown 13 years ago, and why it is he who will be the first right hander to benefit from the new market of bloated TV deals.
Since Brown signed his seven year $105 million deal with the Los Angeles Dodgers in 1999 there have been 33 additional $100 million contracts signed in major league baseball. There have been 0 given to right handed starters in that time. This is a fact almost as unbelievable as teams who dish out $100 million contracts in general.
But it’s true. Here is the list from Cot’s Baseball Contracts. Note: contract information is unofficial and collected from various published reports. Dollar figures not adjusted for deferred money.
|
1 |
Alex Rodriguez |
$275,000,000 |
(2008-17) 10y |
Signed with NYY |
|
2 |
Alex Rodriguez |
$252,000,000 |
(2001-10) 10y |
Signed with TEX |
|
3 |
Albert Pujols |
$240,000,000 |
(2012-21) 10y |
Signed with LAA |
|
4 |
Prince Fielder |
$214,000,000 |
(2012-20) 9y |
Signed with DET |
|
5 |
Derek Jeter |
$189,000,000 |
(2001-10) 10y |
Signed with NYY |
|
6 |
Joe Mauer |
$184,000,000 |
(2011-18) 8y |
Signed with MIN |
|
7 |
Mark Teixeira |
$180,000,000 |
(2009-16) 8y |
Signed with NYY |
|
8 |
CC Sabathia |
$161,000,000 |
(2009-15) 7y |
Signed with NYY |
|
9 |
Manny Ramirez |
$160,000,000 |
(2001-08) 8y |
Signed with BOS |
|
10 |
Matt Kemp |
$160,000,000 |
(2012-19) 8y |
Signed with LAD |
|
11 |
Troy Tulowitzki |
$157,750,000 |
(2011-20) 8y |
Signed with COL |
|
12 |
Adrian Gonzalez |
$154,000,000 |
(2012-18) 7y |
Signed with BOS |
|
13 |
Miguel Cabrera |
$152,300,000 |
(2008-15) 8y |
Signed with DET |
|
14 |
Carl Crawford |
$142,000,000 |
(2011-17) 7y |
Signed with BOS |
|
15 |
Todd Helton |
$141,500,000 |
(2003-11) 9y |
Signed with COL |
|
16 |
Johan Santana |
$137,500,000 |
(2008-13) 6y |
Signed with NYM |
|
17 |
Alfonso Soriano |
$136,000,000 |
(2007-14) 8y |
Signed with CHC |
|
18 |
Vernon Wells |
$126,000,000 |
(2008-14) 7y |
Signed with TOR |
|
19 |
Barry Zito |
$126,000,000 |
(2007-13) 7y |
Signed with SFG |
|
20 |
Jayson Werth |
$126,000,000 |
(2011-17) 7y |
Signed with WAS |
|
21 |
Ryan Howard |
$125,000,000 |
(2012-16) 5y |
Signed with PHI |
|
22 |
CC Sabathia |
$122,000,000 |
(2012-16) 5y |
Signed with NYY |
|
23 |
Mike Hampton |
$121,000,000 |
(2001-08) 8y |
Signed with COL |
|
24 |
Jason Giambi |
$120,000,000 |
(2002-08) 7y |
Signed with NYY |
|
25 |
Matt Holliday |
$120,000,000 |
(2010-16) 7y |
Signed with STL |
|
26 |
Cliff Lee |
$120,000,000 |
(2011-15) 5y |
Signed with PHI |
|
27 |
Carlos Beltran |
$119,000,000 |
(2005-11) 7y |
Signed with NYM |
|
28 |
Ken Griffey Jr. |
$116,500,000 |
(2000-08) 9y |
Signed with CIN |
|
29 |
Jose Reyes |
$106,000,000 |
(2012-17) 6y |
Signed with MIA |
|
30 |
Kevin Brown |
$105,000,000 |
(1999-2005) 7y |
Signed with LAD |
|
31 |
Ryan Braun |
$105,000,000 |
(2016-20) 5y |
Signed with MIL |
|
32 |
Ryan Zimmerman |
$100,000,000 |
(2014-19) 6y |
Signed with WAS |
|
33 |
Carlos Lee |
$100,000,000 |
(2007-12) 6y |
Signed with HOU |
|
34 |
Albert Pujols |
$100,000,000 |
(2004-10) 7y |
Signed with STL |
The first things we take a look at are the splits. There have been 34 total $100 million contracts in baseball history (some haven’t even been played yet, see Ryan Braun). Obviously, Alex Rodriguez and CC Sabathia are special cases as they both opted out of their original $100 million contracts and re-signed new $100 million contracts, putting themselves in a unique class only held by…themselves. However, both contracts count and are included since they are all separate entities.
Including Brown, only seven pitchers have signed a $100 million contract during that time, and all aside from Brown have all been left handed. Carlos Zambrano is the highest paid right handed pitcher sans Brown in the history of the game, his deal was five years, $91.5 million (and ends after the 2012 season).
Rosenthal was particularly irked by this fact, asking:
"Does anyone seriously believe that Brown and Zambrano still deserve to rank 1-2 in total value, especially when baseball is generating far greater revenue than it did in ’07 and especially ’98?"
Well, first, let’s take a look at the highest paid right handed pitchers in history:
|
1 |
Kevin Brown |
$105,000,000 |
(1999-2005) |
Signed with LAD |
|
2 |
Carlos Zambrano |
$91,500,000 |
(2008-12) 5y |
Signed with CHC |
|
3 |
Jered Weaver |
$85,000,000 |
(2012-16) 5y |
Signed with LAA |
|
4 |
A.J. Burnett |
$82,500,000 |
(2009-13) 5y |
Signed with NYY |
|
5 |
John Lackey |
$82,500,000 |
(2010-14) 5y |
Signed with BOS |
|
6 |
Justin Verlander |
$80,000,000 |
(2010-14) 5y |
Signed with DET |
|
7 |
Felix Hernandez |
$78,000,000 |
(2010-14) 5y |
Signed with SEA |
|
8 |
Pedro Martinez |
$75,000,000 |
(1998-2003) |
Signed with BOS |
|
9 |
Roy Oswalt |
$73,000,000 |
(2007-11) 5y |
Signed with HOU |
|
10 |
Roy Halladay |
$60,000,000 |
(2011-13) 3y |
Signed with PHI |
|
11 |
Derek Lowe |
$60,000,000 |
(2009-12) 4y |
Signed with ATL |
|
12 |
Kevin Millwood |
$60,000,000 |
(2006-10) 5y |
Signed with TEX |
|
13 |
Pedro Martinez |
$53,000,000 |
(2005-08) 4y |
Signed with NYM |
|
14 |
Jake Peavy |
$52,000,000 |
(2010-12) 3y |
Signed with CWS |
|
15 |
Ryan Dempster |
$52,000,000 |
(2009-12) 4y |
Signed with CHC |
|
16 |
Chris Carpenter |
$50,800,000 |
(2008-11) 4y |
Signed with STL |
|
17 |
Jason Schmidt |
$47,000,000 |
(2007-09) 3y |
Signed with LAD |
|
18 |
Tim Lincecum |
$40,500,000 |
(2012-13) 2y |
Signed with SFG |
|
19 |
Roy Halladay |
$40,000,000 |
(2008-10) 3y |
Signed with TOR |
|
**please note: I did my own research for this particular list using Baseball Reference since I somehow couldn’t find a list with reliable sources. |
||||
The glaring fact in these contracts are that, aside from Brown’s seven year deal, Pedro Martinez is the only other right handed pitcher given a contract longer than five years (his was six). The left handed pitchers with $100 million contracts (in the first table) Sabathia, Lee, Santana, Zito, and Hampton were all given five year deals or more which explains the increase in the total committed amount (a theory behind that is because elite left handed pitching is harder to find than elite right handed pitching, and another theory is that both New York clubs are on the list, the free spending Phillies are on that list, and the outlying moronic contracts given to Zito and Hampton from San Francisco and Colorado are on the list, making the left handed pitchers more outliers than trend setters).
The fact is, there is no bias against right handed pitchers, which is the tone you took away from Rosenthal’s column. There isn’t much different in a right hander’s average annual value than left handed pitchers, or even that much AAV difference between pitchers and position players.
The glaring differences are in the total contract amounts because there are glaring differences in the years that teams are willing to commit to pitchers. Given that the risk of injury is far greater in pitchers than hitters, you can see why teams are less inclined to give pitchers anything over five years.
The last giant free agent pitcher, Cliff Lee, signed his giant $125 million contract with Philadelphia, but it was for five years. The Phillies General Manager, Ruben Amaro Jr. was willing to give Lee more AAV ($25M per) than years. Part of that is because Lee will be 37 years old at the end of the fifth season, part of that contract is because there were multiple teams competing for Lee’s services and the price was being driven up by agents.
Justin Verlander and Jered Weaver both signed extensions with their current teams and aren’t going to hit the free market for years. You can safely assume that since teams are aware of the rarity of their stud pitchers they are more inclined to sign them before they hit the open market (even if Scott Boras is involved).
Given all this information, it’s going to be very interesting to see the contracts handed to Matt Cain, Tim Lincecum, James Shields, Zack Greinke, Dan Haren, Ervin Santana, Matt Garza, and Josh Johnson over the next two years, given the impact the new TV deals having on individual club finances. Will we see Brown and Zambrano overtaken as the richest right handed pitchers in the game, or will age and injury concerns still trump a team’s willingness to commit years and millions?
I guess it depends on who actually hits the open market, because once they do…well, Albert Pujols and Prince Fielder can certainly explain to you the end game there.
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Good stuff Joshua
I look forward to reading your posts in the future as well.
I guess it depends on who actually hits the open market
I think this really is the key to the whole thing. Looking at your list, I think there is little doubt that a couple of those guys like Verlander, Hernandez, and Halladay would be getting $100 million contracts.
Lincecum looks like the only other potential $100 million guy on the upcoming FA list, but hey, what do I know, stranger contracts have been given out.
"I never knew how someone dying could say he was the luckiest man in the world. But now I understand."
~Mickey Mantle's farewell address
by LaserVortex888 on Mar 12, 2026 5:30 PM EDT reply actions
Thanks guys!
One thought I had that about Halladay:
I wonder if Philadelphia would extend him for another 5 yrs at $100m at the end of his current deal? Given his work ethic and chance at 300 wins I think he could be a very good potential for that…
@walkoffwoodward | www.walkoffwoodward.com
by joshuaworn on Mar 13, 2026 12:02 AM EDT reply actions
I can't see it happening
Only because he will be 36 and a 5 year deal just doesn’t sound like a good idea. If you told me a year ago that the Phillies locked him up for 5 years I could believe it, but not 2 years from now. I see him getting a two year deal, maybe 3 if he can prove to stay healthy over the last two years of this deal.
"I never knew how someone dying could say he was the luckiest man in the world. But now I understand."
~Mickey Mantle's farewell address
by LaserVortex888 on Mar 13, 2026 1:05 AM EDT up reply actions
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