I mean I'm not sure what to tell you. The moment they decided to reduce payroll to the $105-110 mil range it instantly became a 3+ year rebuild on top of the 2 years they had already been bad. Based on what I've read about their financials, it's entirely possibly that they simply needed to because the MLB rules about team debt in regards of revenue. Bleacher nation had a good article about where their money has gone under Theo et al. We'll never know entirely the truth of the matter but the numbers make sense.
The $105-110 mil budget immediately changes the way you approach things. If you look at the off season prior to 2012, Theo and co apparently had a $105-110 mil budget of which Soriano was set to make $19 mil, Zambrano was set to make $19 mil, Dempster was set to make $14 mil and you had Pena and Ramirez hitting FA. The 2011 team won 71 games. That's about as shitty of a situation as you can be in. You had 3 players making $52 mil of your $105-110 mil budget and you're losing 2 of your top 3 hitters as well as needing a RF and 2 starters. Objectively looking at that scenario there's really no surprise they won only 61 games.
Last year their 3 best young players weren't that good(Castro, Shark, and Rizzo) and their biggest FA tanked as well. I'm not going to suggest that outcome is surprising given what was around them but they simply needed those players to give them more than they did because they clearly are trying to clear the books of older players making lots of money and get younger and it didn't happen. So, as I've long said, I'm not sure what exactly Theo's front office was suppose to do in 2 years given the situation. Maybe I'm wrong about the budget of $105-110 mil payroll but Theo has said he spent every penny in the budget the first 2 years and there's no evidence to the contrary. As for the Ricketts in the first 2 years, it's hard to say. I seem to recall the sale being late in the offseason which probably lead to the first year being fairly hands off. Hendry entering 2011 on the hot seat likely didn't help matters either.
What I can say is anyone who's built an business organization should understand it's about assembling the right people and that takes time. It seemingly took them 2 years to find "the guy" in Theo. Theo then had to assemble people under him such as scouts, analytics.....etc. Then all of those people have to find the right players. You have to remember that the 2009 era cubs were far from a model franchise. They were one of the last to embrace the analytical aspects of the game. Their farm system regardless of what it may have been rated at the time simply hasn't produced much MLB talent in the past 5-10 years.
If you were to bring Theo and Co into some other teams they likely could have a very similar impact that he did when he was hired by the Red Sox. The Sox needed fine tuning not a complete overhaul. And on top of that, having them drop from the $140ish mil range to $105-110 really cripples their ability to start quick. If they were the dodgers or the Yankees where money isn't an issue then again, they could have shortened some of the pain we are now having. What this really goes to show is how poorly the Trib ran the cubs. There are numerous issues that have huge ramifications today. For example, had the tribune thought ahead and purchased the buildings surrounding wrigley or at least forced the the rooftop owners out of business the sign issues are gone. The TV contracts are yet another area that set the current cubs back. The lack of embracing analytics for so long is on them. The lack of maintenance on wrigley itself is on the tribune. The fact the cubs didn't have a latin american facility to begin with is on them.
We can go on and on about things that they didn't do correctly. These are all things that the current owners now are having to fix. I'm not saying they should be lauded with praise for building a latin american facility. But, all of the shit they've done is stuff that's need to be done.
