The CBS deal stipulated that the network would pay Letterman a penalty fee of an astounding $50 million if he did not get a show in the 11:30 time period. In other words, any deal presented by NBC had to guarantee Letterman the “Tonight” show time period or else pay him an extra $50 million. What CAA was attempting to do was ensure that no NBC deal could truly match the CBS offer if it did not give Dave an 11:30 show.

