“We’ll take a dozen oysters too,” he said, not bothering to ask me if I wanted any. We’d eaten so many dinners with the Dillons at that point that we all knew each other’s likes and dislikes.
We talked about random things for a few minutes before I said, “Okay, so tell me. Before you get called away on a presidential emergency. Tell me everything you do as the deputy director of political strategy.” I said his title with exaggerated awe.
“Everything?” he asked, raising his eyebrows.
“Everything.”
I let Jimmy talk for almost twenty minutes. I had some sort of idea about what he was doing, from things Matt had said to me or conversations we’d had when we were out—I knew he always traveled with the President, that whenever Obama was photographed, you almost always saw Jimmy standing just to the right of him. Sometimes you’d just see half of his face or one arm, but if you looked for him (which I always did) you could find him. It was like a presidential Where’s Waldo? game. But I didn’t completely understand what his responsibilities were, what it was he actually did.
“So, anytime the President goes anywhere,” he started, “he meets with different political people. If he’s going to Philly, then Ed Rendell will probably meet him at the airport. Things like that. So, I’m in charge of contacting those people, of figuring out who he should see in each city, and then setting it up. Does that make sense?”
I nodded, and he continued. “And then sometimes it’s not politicians, sometimes it’s celebrities that are coming to meet him in the photo line or attending an event. So I’m the contact for them, I facilitate that meeting.”
“And that’s why Scarlett Johansson sends you texts?” I asked. This had happened while we were out to dinner not long ago, and Jimmy had left his phone on the table, so that we could all see when the name Scarlett popped up on his screen.
“Exactly,” he said. “That, and because I’m charming company.”
“Of course,” I said.
Through Matt, I knew that because Jimmy was Jimmy, he befriended almost every celebrity he met, would have drinks with them if they came to DC, offered them private West Wing tours. He showed up on the Instagrams of actresses, as they posed for selfies in front of the Rose Garden. Behind his back, all the people at work made fun of him a little bit, rolled their eyes as he held his phone and pretended to complain that another beautiful actress was texting him, that he’d been out for drinks with Bobby De Niro. But underneath it all was always, I think, a little current of jealousy.
Jimmy was often a ridiculous person, but that didn’t stop us from wanting to hang out with him. He’d look at his reflection in the mirror, admire himself, striking dumb poses and saying, “Can you believe I’m this handsome?” When he walked into a party, he’d raise his hands and announce, “Hey-o! I’m here! The wait is over, everyone, Jimmy Dillon has arrived.” But to be fair, he also made everyone around him feel good—he was quick with compliments and conversation and (while I never would’ve said this to anyone because it sounded crazy) he had a nice energy about him.
He created a Wikipedia page for himself, complete with a head shot and a description of his career that made him sound incredibly successful, almost like he was just days away from running for president himself. His huge ego was made tolerable by his sense of humor, and even when you were rolling your eyes at him or in disbelief about something he said, it was hard to deny that there was something special about him. People wanted to be around him, I think, because it felt like he was going places.
In the meantime, Matt was getting frustrated with his job search, had been in constant contact with the Presidential Personnel Office, met people for drinks a few times a week to talk about different ideas, but still hadn’t had a real interview or even figured out exactly what it was he wanted to do. All he knew was that he didn’t want to be in the White House counsel’s office anymore. And the contrast between his current job and Jimmy’s didn’t help—he was in an office all day while Jimmy was having drinks with famous people. It was just extra salt to rub in his wound.
“So, you like this job?” I asked Jimmy at the end of our lunch. “You’re happy?”
He didn’t even sound a little bit jokey as he said, “I feel like it’s what I was born to do.”
—