I was hoping that, as one of the few libertarians with direct access to Trump, Napolitano might have approached Trump to ask for pardons for Assange, Manning, Snowden, and Ulbricht.All these people deserve pardons, not all but most are even heroes, but I am quite confident the Judge did not request a pardon for any of these people.
I am pretty sure I have a good understanding of the situation and the person Napolitano would have requested a pardon for deserves one and it will be interesting to see what pardons come down around Christmas 2020 after the elections.
Trump is in way over his head when it comes to presidency and economics and foreign policy but he is very street smart. If he would have told Napolitano a pardon was coming that would certainly have been viewed as obstruction if it got out. He instinctively knew it was a dumb move to discuss with Napolitano even if he is considering a pardon down the road.