Back in 2013, CBS announced that David Letterman’s contract had been extended for two years .
But in the book “Powerhouse” by James Andrew Miller, Letterman says of his decision to retire:
The last contract was for only a year. I was frightened then that I might not even be able to make it through the year. Everything had stopped being what it was and I didn’t want to be the last old guy in late night. And this had been an ongoing conversation. Every time I saw Les, I would say, “You know, Les,” I said, “I’m ready to go any time you need me to go.” And he said, “Everything’s fine. Don’t worry about it. Everything’s fine.” And then when Jay retired, I just thought, Oh, yeah. I’m going to be the last old guy. So that was as meaningful to me as anything else. I just thought, I can’t be the old guy trying to keep up with the kids on late night.
Lee Gabler, Letterman’s agent at CAA, says in the book that “60 Minutes” was interested in Letterman. (He doesn’t say it, but you could see Dave as the Andy Rooney.)
When the Late Show ended, I sat down with Dave and said, “What do you want to do?” And he said, “I don’t know,” and I said, “Well, why don’t we sit down with CBS and come up with a post-term deal?” And 60 Minutes was interested in making a deal with him. Sunday Morning was interested in making a deal. CBS Radio wanted to make a deal. There was conversation about a lecture tour in some kind of a format that he would feel comfortable with, but it turned out he really didn’t want to do anything at that point.
Instead, Dave grew a beard.