Maureen Callahan takes a closer look at Bill Belichick's disturbing new romantic relationship with a girlfriend almost 50 years younger than him. Then she goes all in on Gayle King, Oprah and their elitist cronies, flaunting their extreme wealth on social media, and exposes their ties to Diddy.  Plus, Hilaria and Alec Baldwin's failed reality series and their desperation for a reputation rebirth. And the bizarre sexual identity trends of celebrities.