Ideally, yes. However, you can succeed even if you're not in an ideal situation. The position the Cubs are in has them with a couple guys with fringy superstar potential (McNutt, Brett Jackson), a huge boom/bust guy (Vitters), and a ton of players who project to anywhere from decent ML starters to very good starters. Ideally you have more superstar caliber guys in your system, but the Cubs don't. There's nothing you can really do about that in the short term, however, so the key is working with that the best you can. If you can fill 20-23 spots on your roster cheaply with those guys, then you combine the third highest payroll in the majors and you have more money than most teams to go get a couple of guys like Pujols, Fielder, Hernandez, Votto, Kemp, Reyes, etc. Is it the best position to be in? No, but it's a very winnable situation given the upcoming options in free agency, the money the Cubs have to spend and Hendry's ability (if he's still the GM after this year) to go out and get good values in trades.