The Cubs are just coming out of the dark ages as far as prospects go. They had a horrible run in drafting from 2002-2006 (Hendry's biggest mistake in his entire career was not making a change on this earlier) which led to having to buy so much talent from 2007-2010. I wouldn't call Soto or Castro role players though. They'll probably both be legitimate All-Star quality players at their position for several years. Cashner has that type of capability in him. But yes, the Cubs system doesn't seem to be designed to produce superstars. And that's an ok strategy when you think of this question. Where are baseball teams most inefficient? Usually it's at 2B, SS, the bench, 3rd/4th/5th starters, and the bullpen. Since there is a scarcity at all those positions, teams tend to overpay for bad players there. If the Cubs can develop good players at those types of positions (plus at C) it gives them a lot of money flexibility to go out and buy elite bats for the corners. I look at the Cubs over Hendry's tenure as 3 eras (and getting close to entering a 4th). 2003-2006- this was a period where the future got bleaker for the Cubs every single year. Hendry did a pretty good job of restocking the offense but between the young pitching getting hurt and the minor league drafts consistently being bad by 06 there was very little hope. The organization was in a complete mess both in the majors and minors 2007-2009-the Cubs decided to make a run for it right then. This part I blame on the ownership change. A responsible owner would have fired Hendry after 2006 and attempted to slowly build up the team and farm system instead of trying to suddenly buy a winner. Hendry actually did an admirable job building that team together though. He avoided most of the free agent land mines. The 2006-2007 offseason was particularly impressive where the Cubs spent a ton of money and only came out of it with 1 bad contract relative to production when there were tons of horrid contracts handed out that offseason. But it was still the wrong strategy to take because even though Hendry did a lot right, you have to be absolutely perfect when just buying a winner without help from your farm and the Cubs weren't perfect. The Cubs did make huge strides in their farm system during this time though. 2009-2011-Ricketts comes in and says that buying a winner. The Cubs continue to develop their farm system. Hendry stops giving out long-term deals. The team slowly starts unwinding the long-term commitments they gave out. The 4th era is when the team really starts sticking their toes into the FA market again and signing a couple long-term contracts to complement the guys they have in their developing core. That will probably come in the next two offseasons.