You cannot retire your campaign until you are debt free by law. This seems like a fine way to go about getting those campaign debts under some sort of control so he can officially end it.
BTW, I read a while back that Clintoons ‘96 campaign is still active because they still owe people money. We are headed towards the 20 year mark on that. LOL.
Charging money to snap photos with celebs is common in the former (and usually is a black tie occasion where they're a select group of VIPs pay handsomely to sit at the same table and have dinner with the candidate), but considered tacky in the latter example. It's rare for politicians to try and squeeze cash out of people when they're posing for informal photos at public events, although Rod Blagojevich made a fool out of himself doing it during the 2011 Chicago Comic Con (but even HE didn't mind talking to people during the event). Some politicians, like Illinois State Sen. Chris Lauzen, don't even charge for photo-ops at their formal fundraiser dinners. He's nice enough to pose for free with you after you paid $25 to get in for dinner.
It's kinda like how you'd expect to see a gratuity fee automatically added to the bill if you're dining at some fancy sit-down Italian restaurant downtown, but what if McDonald's started charging gratuity fees? They'd probably get the same reaction Newt is getting.