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This one will play out on the field, probably a bunch through 2012 at least.
Which hand would you want to be dealt as a GM:
Halladay 34, $20M thru 2013; Lee 32, $24M thru 2015; Oswalt 33, $16M thru 2011; Hamels 27, $9.5M arb-eligible, FA in 2013
Lincecum 27, $13M arb-eligible, FA in 2014; Cain 26, $7M then $15M, FA in 2013; Bumgarner 21, club control, I think 3 more years before arb; Sanchez 28, $2.1M arb-eligible, FA in 2013; Zito 33, $19M thru 2013
Maybe depends on how much you value Bumgarner and whether you think he'll keep up his 136 ERA+ (and 2.2 WAR in just 18 games) at minimal salary.  Seems like, at a minimum, Bumgarner ought to equal Hamels.  Zito is just sunk cost, of course, but he's been giving them 190+ innings of league-average performance, just not $19M worth.
Lee last 3 seasons (ages 29-31): 168, 131, 130
Cain last 3 seasons (ages 23-25): 118, 148, 130
We may think of Lee as post-season gold, but Cain went through this post-season with an ERA of 0.00 in 21.1 innings.  Lee was the LP to Lincecum in the WS.  Twice.
Interested in everyone's thoughts.