Scott Fybush said:They did that. It was called "UPN," and it didn't work so well.
The issue isn't really bypassing Time Warner...it's Tribune. Time Warner didn't own TV stations (except for WTBS/WPCH in Atlanta, which was a special case), and so when it started up The WB, it needed Tribune's big-market stations to provide clearance in New York, Chicago, LA and elsewhere. Tribune took a minority interest in The WB at the time, and when The WB was merged with UPN to form The CW, it apparently gave up that minority interest in exchange for a 10-year affiliation agreement to keep WPIX, WGN, KTLA and the rest of the Tribune group in the CW fold.
That deal is up in 2016, and it will be interesting to see if at that point CBS looks to move CW programming over to KCAL in LA, WLNY in NYC, WSBK in Boston, WPSG in Philadelphia and WBFS in Miami.
As you note, Chicago is probably the biggest bargaining chip that Tribune will likely have in that negotiation. CBS and Time Warner won't want to lose their big clearance in market #3, and there aren't a lot of good options other than WGN.
Scott, I think you meant KTXA in Dallas-Fort Worth. WPSG in Philadelphia is already down with the CW.