President-elect Donald Trump (Molly Riley/AP)

Donald Trump's relationship with the New York City media is, well, complicated. He's been tabloid fodder for years. But that relationship has changed over the past 18 months as Trump transformed from a joke in the 2016 race to the president-elect. Given Trump's already-rocky relationship with the national press corps, I reached out to Joe Pompeo, a New York-based media reporter for Politico to see what Trump's interactions with the New York media can teach us about how he will relate to the press as president. (Make sure to subscribe to Joe's “Morning Media” tip sheet!) Our conversation, conducted via email and lightly edited, is below. 

FIX: Describe Donald Trump’s relationship with the New York City press corps over his decades living in the city.

Pompeo: I think it depends on what faction of the New York City press corps you're referring to. On the one hand, he was this larger-than-life tabloid character. I mean the great Donald-Ivana divorce of 1991 was kind of a major moment in the tabloid war, with The Post and the News trying to one-up each with scoops every single day. Trump also had a direct line to the gossip columnists, and I guess you could say it was a mutually beneficial relationship. He helped them sell papers, they helped build him into this mythical figure. He embraced the tabloids, same way he embraced all that invaluable cable news coverage as his campaign was starting to catch fire. Then there was, say, Spy magazine, the whole “short-fingered-vulgarian” thing. I mean they really skewered him, and Graydon Carter's still been skewering him in his recent editor's letters for Vanity Fair. Really epic takedowns. Then you had journalists like Wayne Barrett and Tim O'Brien who had a traditionally adversarial, ultimately litigious relationship with Trump, with these hard-hitting investigations into his shady business dealings. But I should really just stop talking and direct you to this fantastic video of Mark Singer telling the story of what happened after Tina Brown assigned him a Trump profile for the New Yorker in 1997. I think this pretty much says it all.

FIX: Has Trump’s interaction with the press changed over the years? If so, how? 

PompeoHe used the media to his advantage back then, he uses the media to his advantage now. He was suing or threatening to sue journalists over stories he found to be unfavorable back then, he's threatening to sue journalists over stories he finds unfavorable now. I mean really the biggest change is that now, for the first time, the press is trying to figure out how to cover Trump not as the nakedly ambitious real estate mogul, or the reality TV sideshow, or the birther conspiracy theorist, or even the unlikely campaign insurgent, but as the leader of the free world. It's jarring and unprecedented and messy on so many levels. It's also utterly fascinating. (And maybe a little terrifying?) 

FIX: Prior to this presidential race, how was Trump perceived by the NYC media? 

Pompeo: Hmmmm ... I don't think it would be a stretch to use words like megalomaniac, or carnival barker, or charlatan? Do you? 

FIX: Trump’s son-in-law, Jared Kushner, owns the New York Observer. How seriously is the Observer taken by the New York City media? And is that different than it was before Kushner bought it?

Pompeo: Here's the thing: If I were to tell you that the Observer hasn't been taken seriously or hasn't commanded much influence in New York media circles for some time now, the people who these days run the Observer — which as of last week is no longer a newspaper called “the New York Observer” but a website called “Observer” — would probably counter that I'm part of a club of embittered alumni so loyal to what is perceived as the Observer's “golden era” that we cannot fairly judge its current quality. So let me just say this: When I worked at the Observer during the last few years of the Peter Kaplan era in the late aughts, it was (and had always been) this fiercely reported, elegantly written, brilliantly edited, often hilarious weekly miracle that punched so far above its weight it made you brim with pride to be a part of it. (Keep in mind that Jared bought the paper in 2006 and Peter left in 2009, and arguably some of the most dramatic changes under Jared's stewardship have taken place in the last three years.) Today — and I think anyone who worked there before, oh I dunno 2011 or so, would agree — it is an entirely different publication, top to bottom. When the news came out last week that the print edition was being shut down, Jim Rutenberg tweeted, “Sad for we Observer alum, tho wasn't paper we worked at.” I'd agree with that. Now that it appears Jared is maybe becoming one of the most powerful people in the world via his influence on our president-elect, what does it mean to him any more that he owns “observer.com”? What happens next in his career as a publisher and/or White House official? These are good questions.  

FIX: Finish this sentence: “The lesson the national press should take from Trump’s relationship with the NYC press corps is ______________.” Now, explain.

Pompeo: I'm gonna cop-out here and quote the estimable George Rush, speaking to the New York Times back in April: “It was an early secret of his success that he embraced the media, that he recognized the tabloid circus was a natural arena for someone of his talents, or ego. What you’re seeing on the campaign trail” — soon in the White House! — “is a style he perfected for years.”