Howard probably can't grasp the concept of a person being generous to his workers, as most of the Stern staff lives in poverty, having to rely on outside gigs and show prize money to pay their bills. Pretty pathetic for the "Number 1" radio show of all time.
He also most likely can't imagine anyone having the ability to turn down money. That thought has never made it past his wig.
The reason he dislikes Jay so much is because he's jealous of him. Jay thrives quite well without Howard, doing something Howard himself failed at, a talk show. He took John, who is doing much better since leaving the Stern show. Jay also works quite hard, despite not having to, another concept lost on Howard. Leno stays up late with writers to make his show better each year, not worse like Howard's.
The result? Despite badmouthing NBC for the last year or so, Jay is offered a new show, more money, and probably many perks. Howard? Losing listeners by the day, and bankrupting the company he works for.
While Jay uses his spare time to work on the many cars Howard mocks him for having ......Howard is on the therapist's couch.
Jay is the Gallant to Howard's Goofus.
