The Cubs dreams were crushed and taken in a different path when they could wait on Wood and Prior anymore. The Cubs essentially in a 3 year span lost two number 1 prospects(Patterson and Prior) and Kerry Wood. It made what Hendry wanted to do completely change. Hendry built a pretty young core team. Coming out of 2003, you were looking at Prior, Wood, Zambrano, and another top 5 prospect in Juan Cruz. Then, you were looking at Aramis Ramirez, Corey Patterson, and Hee Sop Choi. Some busted, some got hurt and Hendry was hurting to get talent quickly. Hate to tell you, if Theo has players like this that bust or get hurt in a 3 year span. The Cubs are in a world of trouble again. That would be like Baez, Russell, and Bryant all getting injured or busting. It was horrible fucking luck.
I'm less concerned with that and more with the 2003-2010 drafts. I agree injuries happen and if they do especially the way that happened with Wood and Prior it's a huge setback. However, coming away with Ryan Harvey at #6 in 2003, Tyler Colvin at #13 in 2006 and Josh Vitters at #3 in 2007 really hurts. In 2003, Nick Markakis, Paul Maholm, and John Danks were the next 3 picks. That draft looks to have been some what poor but even if you're talking one of the next 3 guys that's some value there. 2006 seems to be a case of poor timing to be semi-average. Max Scherzer went 11th, Tim Lincecum went 10th, and Clayton Kershaw went 7th. In 2007, Matt Wieters went 5th, Jarrod Parker went 9th, Madison Bumgarner went 10th, Jason Heyward went 14th.
Now hindsight is 20/20 and all and I get that. I'm just saying different choices in those 3 drafts lead us to a totally different 2010-11 regardless of Wood and Prior getting hurt. And that's only really looking at years where you should come away with great talent based on top 15 picks. In 2005, Jacoby Ellsbury, Garza and Rasmus were drafted several picks after the cubs picked Mark Pawelek 20th. In 2008, they got Andrew Cashner 19th which is a strong pick especially that late but injuries mounted. However, I'm not sure that's an excuse for him because it's fairly common issue for pitchers(see: half the top 100 pitchers this year). 2009 they came away with Brett Jackson which looked good for a time but has since soured. Shame they didn't pick a handful of picks sooner as supposedly they liked Mike Trout who went 25th that year. And finally, in 2010, they came away with Hayden Simpson 16th. Yet another year where a few wins cost them a shot at some great talent. Chris Sale went 13th. Matt Harvey went 7th.
Ultimately, those drafts got the cubs into this situation. It's one thing to have a franchise setback with Prior and Wood going down. But, gettng very little out of 8 straight 1st round picks is pretty tough to bear. I'm willing to give a pass on Cashner as it has netted Rizzo. I'm not going to speculate on internal issues possibly being present. It's highly likely there was a giant mandate on Hendry to win now especially in the later years so having a focus entirely on the draft wasn't likely. However, those poor drafts lead to them trading Archer, Lee and others for Garza who further depleted their system when they went for it.
Also, a lot of those drafts show it just doesn't pay to be a 75-80 win team. Aside from the potential assets you get from trading away deadline players, you're talking about a number of years where they just drafted too high for several elite talents.