If the Cubs hire Theo as their GM, it would be a huge mistake. In the next two years, they will trim a sizeable amount of payroll off their team. 134 million payroll in 2011, 72 signed so far for 2012, and 28 signed for 2013. The Cubs are going to have an absolute ton of money to work with, with A-ram, Zambrano, Dempster, Fukodome, Pena and a few other big dollar players are going to be off the roster.
Theo's strength is drafting prospects and building them for the future, but has a severe weakness when it comes to spending money on established MLB players. I would not give 60-80 million dollars worth of free agents per year in 2013 to Theo's hands.