How Far Will Sean Hannity Go?

Among Sean Hannity’s critics, his relationship with President Donald Trump is frequently depicted as nakedly and sycophantically transactional — one career entertainer grabbing onto the coattails of another and hanging on for dear life. But people close to the president and Hannity say this caricature vastly oversimplifies the complicated and evolving alliance between the two men and misunderstands the degree to which Trump, as candidate and president, has come to Hannity’s positions, rather than the other way around.

“A big part of how Trump gauges how things are going is how they play out on television in particular,” a Trump campaign official told me. And long before he began his presidential bid in the lobby of Trump Tower in June 2015, Trump was a frequent viewer of “Hannity.” “From that first trip down the escalator at Trump Tower,” the official went on, “Trump was able to literally speak like he was on ‘Hannity.’ ” As the primaries gave way to the general election, Hannity and Trump’s campaign staff were in touch on an almost-daily basis. “Occasionally, we’d talk on Sean’s show knowing Trump was watching,” Newt Gingrich told me. “The two most effective ways of communicating with Trump are ‘Fox & Friends’ and ‘Hannity.’"