Tastes and technology change are another factor that has to be accounted for. Most of us now use the DVR to time-shift our viewing and the ability to watch on non-TV devices or with special apparatus (i.e., AppleTV, roku) means that those who want to pay to watch will be willing to pay, those that don't want to pay will watch/do something else.

There is a new standard in tv money with the Dodgers deal. We all thought the new Dodgers' ownership group was crazy for what they paid for that team, but then they struck a monumental tv rights deal and proceeded to outspend everyone. The Cubs are one of the few teams that have a pseudo national following. They should be able to extract a huge price for their tv rights, which were always internally subsidized by the Tribune Company.

JORR correctly points out that Wrigley Field is another huge advantage.

The whole package is going to come together someday, and it will be glorious. If you think the Blackhawks or six championship Bulls were a thing, a Cubs World Series will be heaven on earth.