I don't envy the ownership group of the Cubs but at least you guys will flirt with being a playoff team and can have those expectations going into the season more years than not. The Cubs will be like the Maple Leafs, a huge market and brand that people will pay money to see no matter if they're a 70 win team or a 90 win team.
Reinsdorf is completely incapable of building a great team and sustaining that greatness over a half decade. I'd bet the Hawks make it to the WCF before either of these baseball clubs make the playoffs.