Welcome back to The Best & The Brightest, I’m Tara Palmeri. In tonight’s issue, my conversation with former Trump White House political director Bill Stepien, who knows more about the dark art of hoarding and deploying political capital—and about Trump’s misunderstood relationship with it—than perhaps anyone else. Indeed, many of my recent conversations with people inside Trumpworld confirm Stepien’s insights: I’m hearing that, when it comes to his cavalcade of problematic nominees—and particularly Robert F. Kennedy Jr.—he doesn’t believe that their loss would be his loss, and that it’s up to them to cross the finish line. We discuss all that and more, below the fold.

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And now, on to Bill Stepien…

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Tara Palmeri: What does a political director do inside the White House? Bill Stepien: In most White Houses, there’s a focus on helping guide the legislative agenda based on polling data and public sentiment. In a Trump White House, it’s quite different, as you might imagine. There’s a constant focus on races, candidates, and elections. My first two years with the president as political director were spent just feeding information to him—not putting a finger on the scale of, “Sir, you should do this.” People call him and talk about how great they are, or talk about how great their guy or gal is, without providing a full story. My job, as I saw it, was to provide a full political story of a race and give a full picture, so we could have our eyes wide open on whatever political decisions he sought to make. Many things are different eight years later. Most notably, his political strength is much more sizable. Now, you have people beating down the door because he’s at the height of his power. At any point, we would have died to have the poll numbers and strength that he has right now. Trump’s down-ballot endorsements have had a spotty record—and he’s done some unusual ones. For instance, in the ’22 Missouri Senate primary, he offered a kind of double endorsement to both Eric Schmitt and the scandal-plagued former governor Eric Greitens, and he’s done this more than once. Usually, an endorsement is a golden ticket, but Trump doesn’t look at political capital that way. I think people oftentimes have a misguided view of the kind of person he actually is. At the end of the day, he’s a people pleaser. He wants to make people happy. He wants to help people. He wants people to like him, and he wants to like people. The double-endorsement thing isn’t something I’d seen before, but it’s in line with him wanting to please and to help. That’s an example of him doing things his own way, for sure. I think there are different ways to view political capital. Someone I used to work with would often say that you can obtain political capital and keep it in your desk drawer to save and use for a later date—or you can use it and actually expend it for something you want or need. Trump views political capital in the latter category. He gets it. He uses it. And unlike anyone I’ve seen before, he can get more. I’m not sure anyone has really seen an unending supply of political capital like Trump has, and I always laughed when I was in the White House and read stories about how he’d be enraged when one of his endorsees lost a race. He sees these things as wins and losses. He’s very black and white in how he views these races and his decisions. And that extends to cabinet nominees, to legislation, to basically anything he wants. It feels like everybody else is playing political chess, and he’s just like, Whatever… He believes—and he’s right—that with a tweet or a press conference, the news media soaks it up. I don’t think he worries too much about a bad news cycle, because it’s only a matter of hours, not days or weeks with this guy. He’s using his levers of influence to negotiate, to push around, to get people to sit up in their chairs. That’s very different from what we’re used to from the person sitting in that office, but this is the guy.

Let’s talk about his legislative agenda. Senate leader John Thune and Speaker of the House Mike Johnson see two different pathways to passing Trump’s agenda. Johnson is arguing for one massive bill that includes immigration, energy, and Trump’s tax code, while Thune is saying they should push it through two bills. What are the pros and cons of each approach? Candidly, I think they should ask Trump what he wants to do, because if he’s not involved in the process, he’s less apt to engage. And we know he wants to be engaged, because he loves this process of negotiation, having people in the Oval Office going back and forth, battling it out. Besides, we know Trump’s instincts are really good on this. Eight years ago, his instincts were to do tax cuts first, and all the smart people in Washington said, Sir, we need to go after Obamacare first. That was the white whale for Republicans in D.C., and it was more their fight than President Trump’s, and they ultimately wasted time on Obamacare. It didn’t go down as intended. It was weakening because of that swing and miss, and it took time to get back on track. So they should ask Trump what he wants to do, because who’s going to be a better salesman of this—Donald Trump, Senator Thune, or Speaker Johnson?

What was Trump’s relationship with pollsters when you were with him in the White House? He liked pollsters when their numbers were good, and he didn’t like them when they were bad. He looked at polls, but he was far from obsessed with them. He paid attention when you had something to show him, but he was guided more by his instinct than he was by a pollster’s number that was published somewhere. He used polls to verify his instincts, but they weren’t guiding his agenda or thought process. One of Trump’s greatest strengths is messaging. In his first term, he fired off a flurry of executive orders that were pretty much toothless and couldn’t be upheld in court. How much of this is Trump’s way of sending a message to the American people that he’s trying to make good on his promise, and if it fails, it’s not because of him? From my perspective, those are less legislative documents than they are guiding principles and shows of strength. They’re more, I’m doing on Day One what I promised to do and what you elected me to do. Most Americans don’t know what the hell an executive order is, or if something is subsequently held up in the courts, or overturned. They see him sitting at his desk with a big pen and a document with his big signature on the piece of paper. And it’s the picture and messaging that matters a whole lot more than what happens after. Candidly, people are going to pay attention to what pictures they see on Day One. Do you think Trump is genuinely eager to expand the power of the executive branch? I don’t know the answer to your question. I would say the thing he can do most to have expansive powers is continue to do what he’s doing right now. Right now, he’s so much stronger than he was eight years ago, when Americans gave him even marks and his approval rating was plus-one. Now, it’s approaching plus-20. You can do a whole lot more with the bully pulpit when you’re strong politically. The best way to expand your powers is to look and be strong, and he is.

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