And he failed miserably at that job. The only thing that Hendry failed miserably at was winning a WS. If you judge his success by playoff appearances, he was in the top 1/3 of GMs from the NL during his tenure with the Cubs. Too many peaks and valleys. Hendry could spend money, but he was awful at organization building. Top tier GMs build clubs that sustain success (Yankees, Red Sox, Braves, Cardinals), not winning in fits and starts bridged by periods of being awful. Hendry's tenure mas marked by too much living in the moment, too few contingency plans and too little long term planning. And, to be fair, a solid dose of bad luck. At the end of the day, it's hard to regard Hendry as anything other than a mediocre GM. That is not accurate at all. Hendry's teams had more playoff appearances during his tenure than all but 4 teams in the NL. That is not mediocre. Hendry was definitely an all in type gambler, but it was nice to know that every year he was going for it. With the payroll and resources the Cubs have, there is no excuse for fielding a team as bad as this year's team. I realize what Theo and Jed are trying to do, but they were not honest when they talked about a "dual fronts" approach to rebuilding. The team had more than enough resources to field a respectable team, but instead went cheap and got what they paid for. Every person who knew even a little bit about baseball knew that they weren't trying to win this year. I just hope next year, the front office makes an attempt at improving the major league club.