It has to be a top 5 (maybe 3), 9 figure contract for a SP of all time. Finally had time to put this together. Full list of $100M+ contracts for pitchers per Cots. This isn't just free agent deals though, if that's what you meant (Verlander, for example, had two years left on his deal before his extension in 2013). So if you meant FA deals, I didn't sort for that. This is also WAR over the length of the contract, not just with the team that signed the player to the contract. It also doesn't factor in if a player opted out, like Sabathia did during his first deal. So true FA deals for guys who stuck around, Scherzer and Sabathia were definitely better. Greinke's Dodger deal would have been had he not opted out. Lee's was better because of how much value he provided in only four years. The rest either were worse or were extensions.
Pitcher Years Dollars bWAR fWAR
David Price 16-22 $217M 10.4 10.6
Clayton Kershaw 14-20 $217M 32.5 34.1
Max Scherzer 15-20 $210M 34.9 32.9
Zack Greinke 16-21 $207M 17.0 15.7
Justin Verlander 13-19 $180M 35.7 33.6
Felix Hernandez 13-19 $175M 16.4 15.9
Stephen Strasburg 17-23 $175M 15.2 14.0
CC Sabathia 09-15 $161M 21.3 24.5
Masahiro Tanaka 14-20 $155M 16.9 18.2
Jon Lester 15-20 $155M 13.8 17.0
Zack Greinke 13-18 $147M 29.5 23.2
Cole Hamels 13-18 $144M 26.3 20.9
Johan Santana 08-13 $138M 15.3 13.9
Johnny Cueto 16-21 $130M 8.7 6.3
Matt Cain 12-17 $128M 2.7 3.9
Barry Zito 07-13 $126M 2.4 6.5
CC Sabathia 12-16 $122M 7.0 10.0
Mike Hampton 01-08 $121M 2.9 8.8
Cliff Lee 11-15 $120M 20.2 19.7
Jordan Zimmerman 16-20 $110M 1.2 4.8
Kevin Brown 99-05 $105M 22.8 27.4
Homer Bailey 14-19 $105M 0.4 5.7
Contract not long enough: Cole (20-28), Strasburg (20-26), Sale (20-24), Corbin (19-24), deGrom (19-23), Darvish (18-23), Wheeler (20-24) Pretty cool that Lester and the guy the Cubs initially targeted (Tanaka) are so close.