A key piece of covering the N.F.L.’s quarterly league meetings, as I have for a dozen years as a sportswriter for The New York Times, is trying to get the tight-lipped, billionaire team owners to talk about issues of the day. Mostly, it’s a fool’s errand. Few of them want to talk to the media, let alone be seen talking to you, and when they do talk, they are often guarded.

But the two most powerful owners—Jerry Jones, 83, of the Dallas Cowboys, and Robert Kraft, 84, of the New England Patriots—routinely speak with reporters, and their interactions say much about who they are and how they want to be perceived. Take the three-day owners’ meeting in 2023 at the Frank Lloyd Wright–inspired Biltmore hotel in Phoenix, Arizona.