Wins/dollars is a terrible way to evaluate a GM. You never know who the guy actually targets, if a player he coveted for various reasons had a bigger desire to play elsewhere. Things like that. Of course a team with a big payroll that has sat around 500 during a GMs tenure is going to be near the bottom in wins per dollar (which is still, and has always been a terrible way to think of players "value"). All it says is that we have had a poor ability to develop our own talent to go with the money he has spent. It's not as if he is trading away our young talents, it's that we simply haven't done that much. Jim Hendry hasn't been any worse than Theo Epstein on FA/Extension's (Julio Lugo), Billy Beane (Eric Chavez), and you can go on. The difference is that Epstein's farm system has been fairly productive (thanks to more $$$), and all the other "good" GMs with a high wins per dollar have all been the beneficiary of successful farm systems (which are usually built in their predecessors tenure). He's average for signing free agents sure the Soriano deal may have been bad, but Ted Lilly was great. He's very good at finding castoffs that actually do well. Michael Barrett, Tom Gorzelanny, Ryan Dempster, etc. He's always been a solid guy in trades. He's also done relatively well when trading guys for prospects (Archer, Ceda, etc). The only thing that has kept the Cubs from going to the playoffs more often under his tenure has been a system producing one or two impact bats. An Albert Pujols, an Evan Longoria, a Joe Mauer, a Justin Morneau, a Joey Votto, a Prince Fielder, a Ryan Braun, etc. Those are the types of players that create high wins to dollar spent ratios. I'm not sure how much fault Hendry is at not producing one. Typically those players are top five picks, and we've had one top five pick in his tenure and we picked a guy that was a consensus top five pick. You can say Soto is an impact bat, but Soto's only been one in two of the years Hendry's been here - and in one of those years we won more games than any Cub team since World War II.