Bossie, now Bannon's deputy campaign manager, was involved in the day-to-day management and hundreds of daily decisions and quickly learned who had the real authority. He would be in a meeting with Bannon, Conway and Kushner, where a decision would be made: for example, on the next three TV spots.
Bossie would pass the decision to the person running digital ads, but then see that they didn't run. "What the hell!" he said. "I came in here. I told you what to do. We had a meeting, we decided."
"Oh, no, no," he would be told. "Jared came in after you and said, 'Don't do that.' "
This was a "very important light bulb moment." If Kushner didn't fully buy in, things wouldn't get done. So after decision meetings, Bossie approached Kushner to make sure he understood what Jared wanted. Kushner, without the title, was running the campaign, especially on money matters. He knew that his father-in-law considered it all his money and Jared had to sign off on everything.
Kushner scoffed at Bannon's suggestion that Trump put $50 million of his own money into his presidential campaign. "He will never write a $50 million check," Kushner told Bannon in August.
"Dude," Bannon said, "we're going to have this thing in a dead heat." They would soon be tied with Hillary. "We need to finally go up on TV with something." They needed to contribute to the ground game. "We're going to need at least $50 million. He's going to have to write it."
Under election rules and law, the candidate can make unlimited personal contributions to his or her own campaign.
"He'll never do it," Kushner insisted.
"It's about being president of the United States!"
"Steve, unless you can show him he's a dead lock" - a certain winner - "I mean a dead lock, up three to five points, he'll never write that size check."
"Well, you're right," Bannon agreed.
"Maybe we can get $25 million out of him," said Kushner, adding a caveat: "He doesn't have a lot of cash."
After the final presidential debate in Las Vegas on October 19, Trump returned to New York. It was now the three-week sprint to election day!
Bannon, Kushner and Mnuchin, the former Goldman Sachs executive, presented Trump with a plan for him to give $25 million to the campaign.
"No way," Trump said. "Fuck that. I'm not doing it." Where were the famous Republican high-donor guys? "Where the fuck's the money? Where's all this money from these guys? Jared, you're supposed to be raising all this money. Not going to do it."
The next day they came up with a new proposal for $10 million and presented it to Trump on his plane. This wouldn't even be a loan, but an advance against the cash donations coming in from supporters. These were the "grundoons" or "hobbits" as Bannon playfully and derisively called them. And he had a deadline: They had to have the $10 million that day.
The supporters' donations "will keep coming in, win, lose or draw," Bannon said. "But I say you're going to win."
"You don't know that," Trump snapped. "We're three points down." It showed how little confidence Trump had in victory, Bannon thought.
After two days of pushing for the $10 million, Trump finally told them, "Okay, fine, get off my back. We'll do $10 million."
Steve Mnuchin handed Trump two documents to sign. The first was a terms sheet outlining how he would be paid back as money came into the campaign.
"What's this?" Trump asked about the second document. "Wiring instructions." Mnuchin knew that every Trump decision was tentative and open to relitigation. Nothing was ever over.
"What the fuck," said Trump. The wire order should be sent to someone in the Trump Organization.
Mnuchin said no, it needed to be done right' then. Trump signed both documents.
Bob Woodward, "Fear: Trump in the White House" (2018)
