You have to remember that Howard's longtime agent, Don Buchwald, passed away in July last year. Don was crucial to Howard's financial success. Buchwald also had friends of mine as clients, including the late Alan Bleviss. While Howard can afford the highest priced agent, it won't be the same. Buchwald was a decent and honest man and a mentor to many of his clients, including Howard.
There's also little Donny Trump to consider in all of this. Stern has turned against his former regular guest and Sirius, although not regulated by the FCC, may not want to deal with tantrums coming from the thin skinned, spray tanned, gold obsessed man-child in the White House.
Plus, Howard is 71, does many of his programs from his Long Island mansion, and may not feel like continuing. He's often said on and off air, that this current Sirius contract would be his last.
As little Donny often says, "We'll just have to wait and see".