Are you saying you'd rather have "reasonable" contracts no no WS wins? Yes. That is exactly what I said. Sorry, I phrased that incorrectly. You're saying that even if the Cubs won 5 world series' within a decade, you'd be still be bitching about 1 bad contract on the team. No. The point is obviously the end goal is to win the world series, but the same way a world series winning manager isn't automatically good, neither is a world series winning GM, and when you're looking to hire either you don't simply look at what their end results were. Kenny Williams trading Carlos Lee for Scott Podsednik doesn't automatically become a smart move because the White Sox won a world series. Garagiola Jr putting the D-Backs in severe debt doesn't become intelligent because Mariano Rivera blew a save in game 7. The fact that Gillick's protege in Philly thought that contract for Howard was a good idea is something to be concerned about when talking about Gillick. Gooney makes a good point that it hasn't hamstrung them, but the fact that they have a payroll pushing 170M isn't hurting them either. It's a bit of chicken or egg: Did the success of the Phillies lead to the 170M payroll, or is their success a byproduct of said payroll. I'm not trying to argue that Hendry is a better GM than Amaro, or that Gillick will be a failure, but that Howard contract is certainly an eyesore.