This Sept. 29, 2006, file photo, shows Roger Ailes, then Fox News CEO, at Fox News in New York. (AP Photo/Jim Cooper, file)

The New York Times reported Tuesday that former Fox News Channel boss Roger Ailes, who was forced to resign amid sexual harassment allegations last month, is now advising Donald Trump's struggling presidential campaign. That pairing is totally fascinating to me. I reached out to New York magazine's Gabriel Sherman, who wrote the book, literally, on Ailes, for some perspective on their relationship. Our conversation, conducted via email and edited only for grammar, is below.

FIX: What’s the relationship between Trump and Ailes? Are they close? Acquaintances?

Sherman: Trump and Ailes have known each other for decades. They're friends in the "we're-both-Manhattan-media-power-brokers" sense. More recently, Ailes helped propel Trump's unlikely political career by giving him a weekly call-in segment on Fox & Friends. The two lunched shortly before Trump launched his candidacy, and Ailes has given Trump talking points throughout the campaign, people close to both men have told me. Trump's plan to build a wall on the Mexican border is only slightly less extreme than Ailes's immigration proposal: sending Navy SEALs to shoot people crossing illegally.  

FIX: Ailes hasn’t worked on a campaign actively since Dick Thornburgh’s special election loss in 1991. Did he ever express a desire to do so or regret that he couldn’t while at Fox News? And is what Ailes learned from campaigns in the '70s and '80s still relevant today?

Sherman: In 2012, Bob Woodward reported that Ailes said he would quit Fox News to run Gen. David Petraeus's presidential campaign, if he ever decided to run. That, of course, never happened. But I would argue that Ailes never really left working on political campaigns. Throughout his years at NBC in the 1990s and Fox News starting in 1996, Ailes regularly advised and aided GOP politicians during election cycles. 

For instance, in my book, I reported that Ailes edited a four-minute segment that had all the trappings of a Romney attack ad, which ran on Fox & Friends at the outset of Romney's 2012 general election campaign. Ailes also suggested Paul Ryan visit his former business partner (and Fox News consultant) Jon Kraushar for teleprompter coaching. One of the things that made Fox News so influential was that Ailes straddled the world of GOP politics and media. 

What Ailes learned from campaigns in the '70s and '80s is perhaps even more relevant in our ADD media environment today. For example, look at what Ailes once said after running Bush 41's media campaign in '88: "Let's face it, there are three things that the media are interested in: pictures, mistakes and attacks. That's the one sure way of getting coverage. You try to avoid as many mistakes as you can. You try to give them as many pictures as you can. And if you need coverage, you attack."

With media outlets increasingly competing for clicks, Ailes's philosophy is even more true. Candidates need to work harder than ever to capture our attention and the media reward the outrageous at the expense of the substantive. (Remember how Jeb!'s earnest policy-oriented campaign turned out?) Trump has built his entire campaign strategy around Ailes's lessons, and until now at least, it's worked. 

FIX: What does Ailes tell Trump to turn around his campaign?

Sherman: Maybe what Ailes once told Al D'Amato: "Can you fly?" Ailes posed the question during a meeting with D'Amato in a Manhattan skyscraper. As recounted in Lloyd Grove's classic Washington Post Style profile of Ailes from '88, Ailes threatened to throw D'Amato out of the window unless he started listening to him. Given the reports that Trump isn't listening to his advisers, maybe Trump needs the threat of Ailes throwing him out of Trump Tower to get him to focus.  

FIX: Ailes is 76. Is there something after FNC and this campaign for him? What does that future look like?

Sherman: Hard to say. Ailes and the Murdochs have reportedly signed an iron-clad noncompete clause that prevents Ailes from working for a rival news network for four years. That would mean he'd be 80 when he could get back in the media game. Ailes has said he's going to write a book, but he's been saying that for years and hasn't produced anything. His health is faltering — he took extended leaves of absence from Fox in recent years — so it's a real question if he has to the fight in him to stage a final act. That said, this is Roger Ailes, so I wouldn't bet against him. 

FIX: Finish this sentence: “Roger Ailes will be primarily remembered for ________.” Now, explain.

Sherman: "... revolutionizing television news while destroying the Republican Party."

Ailes's skills as a communicator and television producer are unrivaled. He built Fox News from scratch into a network that generates more than $1 billion a year in profit (with twice the ratings of CNN and MSNBC).

But that success came at a cost: Ailes helped to destroy the political party he devoted himself to since 1968, when he helped Richard Nixon win the White House. Ailes's power and ruthlessness — the black lists; his use of surveillance on employees and adversaries; and the smear campaigns he orchestrated —allowed him to take over the Republican Party and mold it to fit his paranoid worldview. Ailes's conspiratorial, divisive and entertaining style of politics may have dominated the Nielsen ratings, but it turns out to have failed as an electoral strategy in presidential politics. 

We saw this dynamic play out in 2008, 2012 and, given the trajectory of Trump's poll numbers this summer, perhaps again in 2016. Ailes's views — and therefore the GOP's views — on immigrants, climate change, taxes and national security are out of step with the mainstream. (After all, is it surprising the GOP is struggling to connect with women voters when the the architect of the party's message saw his career end after being accused of sexual harassment by dozens of women?) 

Roger Ailes stepped down as Fox News chairman and chief executive July 21 amid a sexual harassment suit brought forward by former host Gretchen Carlson. (Erin Patrick O'Connor/The Washington Post)