In theory, the best way to judge general managers might be to measure their wins against their payroll -- whether you have $50 million or $150 million, you can spend it more or less prudently -- but this raises its own issues. Fourteen of the game's 30 general managers have run their team for one or two seasons. Judging them on how well they've dealt with a roster and payroll they may have had little control over isn't really fair. Also, efficiency isn't everything. No team spends more per win than the New York Yankees, but few would say that Brian Cashman is anything other than one of the best in the game at his trade.
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Cashman's weakness isn't a small one -- the Yankees, the only team in baseball to routinely run $200 million payrolls, have recently been spending about four times as much per win as the Rays. Why, then, does he rank so high? His four world championships don't hurt, but the really impressive thing is that since he secured full control over baseball operations after the 2005 season, the Yankees have spent their money wisely, signing studs like CC Sabathia rather than sure bets for decline, and traded smartly, dealing the fruits of a much-improved farm system for players still in their prime, such as Curtis Granderson.
I agree with Marchman's comments completely. I think Brian Cashman has done a terrific job at overcoming nearly a decade of bad habits within the organization, to not only bring them their 27th ring, but also set things up nicely for the next several seasons. What are your thoughts on Cashman and the job he's doing?