Why do you think Rush was being uncomplimentary? I would think Tucker would have liked the comparison.
It was many, many years ago, perhaps coincident with Tucker’s previous work at CNN or MSNBC, and probably was a reference to his youthful, preppy appearance & bowtie. Back then, I had heard his name, but knew little of his ideology, so I won’t speculate on that.
On one show during his last year, Rush spoke of his reference to Tucker as Chatsworth Osborne Jr., but I don’t remember if he fully explained the reasoning. It always struck me as being at least somewhat derisive.
I’m guessing that Rush would be more supportive with the strength of Tucker’s views in recent years, especially the past two or so. His is one of a very few ‘don’t miss’ daily broadcasts for my wife and myself.