Donald Trump, if nothing else, is a man who loves spectacle, and Mayor Rahm Emanuel’s brother Ari may be the one to deliver it at the Republican National Convention this July in Cleveland, according to a new profile of the presumptive GOP nominee by Michael Wolff in the Hollywood Reporter:

He may know few people in Washington, and care about them less, but he knows his [media] moguls and where they rank on the modern suck-up-to list. (…) Among his frequent media and now political confidants is WME co-CEO Ari Emanuel — whose brother, Rahm, the mayor of Chicago, was once Obama’s chief of staff — whom Trump says has offered to take charge of the Trump celebratory convention film.

The connections between Trump and the Emanuel brothers should be no surprise to those following along in Chicago. Trump gave Rahm $50,000 for his first run for mayor, as reported by Carol Felsenthal in Chicago in April 2011. At the time, Trump was making headlines due to his relentless birtherism in demanding that President Barack Obama release his birth certificate and his (then-laughable) claims that he’d run for president himself.

Ari Emanuel, the big-time Hollywood agent who famously inspired Jeremy Piven’s character Ari Gold in HBO’s Entourage, previously represented Trump as an agent and Trump called him a “close friend.” Considering Ari, Rahm, and their physician/bioethicist brother Zeke all maintain close ties to the Obama administration, this may seem odd. But Trump was happy to play up the connection in his recent interview, telling Wolff:

“[Ari’s] a very good friend of mine,” says Trump. “He calls me a lot. I call him a lot and we talk. He’s very political. Even though he’s not political, he’s political. He gets it. You’re shocked to hear that, right? [About the movie.] But yeah, I might do something with Ari. Does he represent you?”

Trumps’ relationship with the Emanuels is yet another contradiction among the many that have come to define the reality TV tycoon’s path to nomination. As Felsenthal wrote in 2011, considering “he changes his mind without worrying if the public notices… [he] once denounced Reagan and ‘W’ as the worst presidents ever, [and] previously pushed for universal healthcare and abortion rights,” Trump could never be the GOP’s 2012 nominee. But Trump also called Obama “the worst president in American history,” and it was that rhetoric five years ago that foreshadowed the populist outrage he continues to tap today.