He tries. But it doesn't work all that often. I don't think they'd actually LIKE him, because whatever we can say about their bad decisions or bad characters, they aren't stupid, and he is. I think they're entirely aware that everything he says and does is about himself.
He wanted Supremes who'd be "his" judges, just as he wanted generals who'd be "his" generals. And neither has really worked out for him. The only people he can be sure of are his cabinet and White House appointments: the Stephen Millers, Kristi Noems, Pam Bondis, JD Vances, Howard Lutnicks and more.
I don't think Trump will ever understand that personal loyalty will never count for much with the Supremes or the Joint Chiefs.