Chris Carpenter is 37 and entering the second year of a 2 year $21mil extention. The age is similar, but the miles (numbers of surgery) are very different. Carpenter also has a vastly superior track record, but as a "traditional" pitcher, one might worry that he is nearing the end of the line. Not so, perhaps with our favorite knuckleballer. Carpenter missed all of 2003 and pitched a combined total of 21.1 IP in '07 and '08. He signed his 2-year extention after leading the NL in innings in 2011 and promptly pitched 17 innings this season. In his career with the Cards he is 95-44 with a 3.07 ERA and a 1.125 WHIP, 7.2 K/9 and 2.0 BB/9, an adjusted ERA of 133.
Zack Greinke, at 29 years old, just finished a 4 year $38mil contract which he signed originally with KC. The fact that he was still arbitration eligible (and therefore under team control) when he signed the deal and that he missed time with anxiety issues are somewhat comparable to Dickey's option year and late arrival to the big leagues. In Greinke's last 5 seasons, he has gone 70-43 with a 3.38 ERA, a 1.197 WHIP, 8.75 K/9 and 2.28 BB/9. His adjusted ERA for his career is 114.
Tim Lincecum is entering the second year of a 2-year $40.5mil contract. Forgetting age for a moment, there has long been an undercurrent of "how long can Lincecum keep doing this" at 5'11" 165 lbs. (The answer may be "not much longer.") That, combined with the fact the Giants had arbitration "control" led to 1 and 2-year deals for Lincecum.
Roy Halladay is 35 and in the middle of a 3-year $60mil contract. I would suggest this is not terribly comparable, except to use as the type of contract that Dickey should not be able to get. Halladay signed the deal at 4 years younger than Dickey is now, already had the track record of dominance and was a free agent.
Lee (5 years $120mil), Sabathia (8 years $182mil), Peavy (5 years $77mil), Verlander (5 years $78.5mil), Felix (5 years $78mil) and Kershaw (2 years $19mil) are not comparable due to each players' youth, track record and/or contract status.
So what do I take from this? I would say Dickey can make a case for being more of a sure thing than Carpenter in terms of fewer miles on his arm and the overall effectiveness of knuckleballers into their 40s though the question of whether his "hard knuckler" changes that equation is a fair one. I would further say that Greinke and Halladay are a "high end" of what he should not be able to surpass. So, somewhere between 2 and 4 years, where can we possibly meet in the middle there? Hmmmm... my math is failing me. And somewhere between $9.5mil (Greinke), 10.5mil (Carpenter) and $20mil (Lincecum/Halladay). I think we're closing in on "Oliver Perez money"! Seriously, is we offer an extention of 2 years $24mil and an option year or two or three at $12mil each, does that not work?