Not to distract from the in depth thread on the Twins forum, but a point raised there has piqued my research interest. Many seem to say that long-term pitching contracts cannot produce any value for the team due to the inevitable decline. I decided I'd use those pitchers who had "earned" a $90M+ overall contract or a shorter term contract with $20M+ AAV. The lists: $90M total contract club - 15 members (don't count CC twice) Clayton Kershaw $215M 7 years, 2014-2020 Justin Verlander $180M 7 years, 2013-2019 Felix Hernandez $175M 7 years, 2013-2019 CC Sabathia $161M 7 years, 2009-2015 Masahiro Tanaka $155M 7 years, 2014-2020 Zack Greinke $147M 6 years, 2013-2018 Cole Hamels $144M 6 years, 2013-2018 Johan Santana $137.5M 6 years, 2008-2013 Matt Cain $127.5M 6 years, 2012-2017 Barry Zito $126M 7 years, 2007-2013 CC Sabathia $122M 5 years, 2012-2016 Mike Hampton $121M 8 years, 2001-2008 Cliff Lee $120M 5 years, 2011-2015 Kevin Brown $105M 7 years, 1999-2005 Adam Wainwright $97.5M 5 years, 2014-2018 Carlos Zambrano $91.5M 5 years, 2008-2012 $20M annual contract club (excluding those who are in the first club) - 3 member, one twice Roger Clemens $28M 2007 Roger Clemens $22M 2006 Tim Lincecum $40.5M 2012-2013 Roy Halladay $60M 2011-2013 So, I'll break them down a little bit. For a guy resigning with his original club when he hits free agency (or as an extension to avoid some arbitration years), there is very good value for the club (even Zambrano, which thoroughly surprised me). As an example of this, Clayton Kershaw will earn $215M starting this year and going into a current 6th grader's senior year of high school. However, including this year's significantly discounted first year of the contract, Kershaw has earned $23,844,000 in his career, and according to Fangraphs, he has delivered $166.4M of value, meaning if he pitches for the Dodgers the entire contract, they'll have paid him roughly $240M total for 13 years of play for their team. They've already earned $166.4M of that money, so Clayton really needs to produce roughly 14 WAR over the rest of the contract to earn the difference, and he's already had a 6.7 WAR season this year on the heels of a 6.6 WAR season last year, so barring injury, the Dodgers will likely make out very well in Kershaw's career. The short term deals pretty much all went belly up. Clemens earned $50M in 2006-2007 and produced $18.9M in value. Lincecum returned $10.7M in value on the Giants' $40.5M investment, though one could use my Kershaw logic to say they were already ahead, paying $24.55M for $110.6M in value produced. Halladay by far came closest to producing value in his short-term, high-money deal, earning $42.8M while being paid $60M. He was coming off a season after the Phillies traded for him where he gave them $24.4M in value for $15.75M in salary, meaning Philly paid $75.75M for Halladay's time with the team and got $67.2M in value, which isn't horrible considering he retired at the end of that contract. The third category is the straight free agent pitchers. These have had varying values. The guys in this category are CC Sabathia's first contract, Greinke, Tanaka, Zito, Hampton, Lee, and Brown. Sabathia currently has produced $112M in value since signing that contract and been paid $132.9M to do it. Not a great value, but certainly not horrific. Greinke has produced $33.5M while being paid $45M since signing his deal. Tanaka produced $16.8M in his injury-shortened season while being paid $22M. Zito was the big flop everyone refers to, producing $24.1M in value, meaning the Giants lost over $100M on the deal in salary paid vs. production. Lee has been one of the better signings, costing the Phillies $82.5M while providing $85.5M in value (and he was signed going into his age 32 season). Hampton and Brown started their contracts before FanGraphs valuation formulas begin, so they are both estimations. Hampton produced an estimated $33.7M in value for his $121M, though a big part of the lost value for Hampton, especially once he ended up in Atlanta rather than Colorado, was the games he missed, only starting 147 games in the 8 years of his contract, missing 2006 and 2007 completely, and only pitching 200 innings once in the entire deal. A bit of trivia on Hampton: he was one of two pitchers not named Greg Maddux to win a Gold Glove from 1990-2009, and all three have Braves ties (you can easily Google the answer, but try guessing first). Kevin Brown was the originator of the $100M pitching contract, and his is still seen as one of the better investments, and the values are hard to measure, but he earned an estimated $67M of value for his $105M cost. What did we learn? Honestly, not as much as you'd like. The free agent pitchers still under contract have earned 88% of their paid value so far in the contracts. Zito earned 19% of his contract, and Hampton earned 28% of his contract while Brown earned 64% of his deal. It is of interest to note that between Hampton and Zito's deals, there was a 6 year hiatus in big deals like this for all pitchers, and in general, the deals signed since Zito's have been fairly successful (or a reward for value already produced in an extension). Here's a quick list on those extensions - total value provided with team, total salary earned thus far, and total salary investment from the team by the end of the current contract: Kershaw - $166.4M value, $23.84M earned after 2014, $240M committed Verlander - $208.8M value, $86.5M earned after 2014, $226.5M committed Hernandez - $210M value, $85.2M earned after 2014, $217.5M committed Hamels - $152.5M value, $78.4M earned after 2014, $180.4M committed Santana - $54.3M value for Mets, $137.5M earned from Mets (career totals of $170.9M value and ~$161.5M earned) Cain - $120.4M value, $71.7M earned after 2014, $144.2M committed Sabathia - $112M value to Yankees, $132.9M earned after 2014 from Yankees, $185.7 committed overall by Yankees (career totals of $243.4M value, $169.4M earned, and $222.4M committed) Wainwright - $147.1M value, $56.2M earned after 2014, $134.2M committed Zambrano - $111M career value, $114M career earnings TL;DR, I know. Sorry. This was just freaking interesting as I dug into it more and more!