The word “luck” is a very important word—very important. There’s no more important word than “luck.” But you can help create your own luck.
—DONALD J. TRUMP, APRIL 24, 1988
YOU MIGHT NOT KNOW IT from looking at him, but Donald Trump is one of the most superstitious men that most people have ever met. Sometimes, he’ll throw salt over his shoulder before he eats. He called Fox and Friends every Monday morning during the primaries because he didn’t want to change a winning routine. And he believes that some people, usually ones with low energy, carry bad luck and need to be avoided at all cost.
If you worked for Mr. Trump, you knew there were certain rules.
We were never allowed to celebrate before a win was certain, and we always had to take our losses with grace. Anything else and you’d invite in some bad juju. It’s the reason that come election night we didn’t have a victory speech—or a concession speech—written ahead of time.
“Don’t jinx me,” Mr. Trump would say.
Who knows? Maybe it’s adhering to all these little rules and rituals that’s kept Donald J. Trump in such good standing with the universe all these years. Like Midas, he’s turned everything he’s touched into gold: real estate, hotels, publishing, television, and now politics. Still, sometimes it astounds us both—the way it baffled the media and half the American electorate for so long—that Donald Trump and this ragtag band of outsiders, misfits, and political neophytes was able to pull off the biggest electoral upset in American political history. Then again, as the boss always reminded us, we had the best candidate to ever put his name on a ballot.
Still, considering how our story turns out, the backdrop of Las Vegas is a pretty good place for it to start.
I t was sometime in 2010 when Dave picked up his BlackBerry, the retro phone he still refuses to part with, and dialed his friend in Vegas. Three-quarters of the way across the country, Steve Wynn took the call in his casino-floor office in “The Wynn,” as they call his five-star hotel and casino, the one with the stunning seventy-foot waterfall that tumbles into a three-acre man-made lake.
The call had little to do with politics. Dave was going to try to ply some swag out of Mr. Wynn for an auction held at the annual golf tournament he ran. “Ply” isn’t the right word. The tournament raised money for the Children’s National Medical Center in Washington, DC, a hospital that Dave knew the inner workings of intimately. Surgeons there had operated on his son, Griffin, when he was just three years old to fix holes in his heart. You see, Griffin was a miracle baby. He had already had a heart surgery at two days old to fix the descending aorta of his heart, which was too narrow to get blood out to his body. Though it was successful, Griffin would have five more major surgeries: one on his heart and four on his brain. Through all of them, Dave and Susan sat anxiously in hospital waiting rooms and on hard benches outside cardiac or neurology operating rooms, waiting for the results. During Griffin’s brain surgery, doctors suggested that Dave and Susan go out and spend a day together in New York City, where they’d gone for a specialist. This might be a long one, they said. Could be up to eighteen hours long. Instead, Dave and Susan stayed near the operating room, knowing the odds of their son surviving were almost unbearably low. The hospital had made them sign papers acknowledging it.
Inside, the team of neurological interventionists took turns going through the veins in Griffin’s brain—his head, because of significant hydrocephalus, was nearly the size of an adult male’s, though his body stayed as small as a toddler’s—and watching it the whole time on multiple high-definition screens above their heads.
Then, just a couple of hours in, something happened. Just as the doctors were getting at the area near his vein of Galen aneurism that they’d gone in to seal up, the blood vessel sealed on its own. The doctors watched on the screen, amazed. They cut the surgery short and paged Dave and Susan, who were getting breakfast with Susan’s sister, Nathalie, who had flown in from Denver to help out. They thought the worst because only a short time had passed.
“Your son’s a miracle,” Dr. Alejandro Berenstein, the lead surgeon, said. “I’ve never heard of anything like that happening, let alone seen it.”
And just like that, in a few hours, Susan and Dave saw hope. Even with three more brain surgeries and one open-heart surgery, Griffin had a future.
So Dave and a buddy, Mike Murray, who would later become one of Ben Carson’s campaign managers, decided to run a golf tournament for the renowned DC children’s hospital, and their friends were always happy to support it. And Steve Wynn, though he was a relatively new friend, was no exception.
Frank Luntz, the coarchitect of Newt Gingrich’s Contract with America, had introduced Dave to Steve Wynn in early 2010. Later, Dave flew out to Vegas and had dinner with Wynn in the steak house in his casino. Dave, the president of a nonprofit conservative political organization, had recently won a lawsuit against the Federal Election Commission in a First Amendment case you might have heard of. The Supreme Court’s Citizens United decision in January 2010 would rewrite US campaign finance laws, ensuring that money spent for political purposes was protected as free speech under the Constitution and couldn’t be regulated by the government. As a businessman and a frequent political donor, Wynn was someone Luntz thought Dave should know. He also thought the two would get along. He was right. They did.
Wynn promised Dave several great prizes for his tournament, including room comps and a foursome at his beautiful Wynn Golf Club, a par-70 course right by his casino in Vegas. Had the phone call ended after Steve Wynn’s display of generosity, Dave would have been perfectly content. But luckily, for our sake, the conversation continued, and that’s when Lady Luck began to smile on our story. Dave mentioned that he held the tournament at what was then known as the Loews Island resort golf club in DC.
“My friend Donald Trump just bought that golf course,” Wynn told him.
Dave doesn’t like to brag, but since we’re writing this book together, he doesn’t have to. He is good at what he does, and you don’t become a political operative of Dave Bossie’s magnitude without recognizing an opportunity when you hear one. He stored the information about Trump and a month or so later called Wynn back.
“You think you could introduce me to Donald Trump?” he asked. Although he didn’t know exactly what Trump would do for him, he figured getting to know the owner of the course where he held the tournament could only have an upside. On this crap table, he saw no harm in throwing the dice.
There wasn’t any harm. Without missing a beat, Wynn called out to his assistant.
“Cindy, get the Donald on the phone for me, please.”
And just like that, Dave was on a conference call with two billionaires.
“Any friend of Steve’s is a friend of mine,” Trump would say after the introductions. “Next time you’re in New York, come see me.”
“Funny,” Dave said, “I’m scheduled to be in New York City in the next couple of weeks.”
As there was no such scheduled trip, Dave made a mental note to make the reservations as soon as he hung up.
When Trump got off the line, Steve Wynn had some parting advice.
“Ask Donald to waive the fee for the course,” he told Dave.
I’m on a roll , Dave thought as he hung up the phone.
T he next week he walked into Trump Tower for the first time in his life with a wish list of auction prizes in his head. In the elevator up to the twenty-sixth floor, where Donald Trump had his fantastic office, Dave started to have second thoughts about this plan he had hatched. Sure, it was for a good cause, but he was about to walk in to see Donald Trump, whom he knew only about as well as you could know anybody from television and a five-minute phone conversation, and ask for stuff. Besides, he was Donald Trump. The Apprentice . The Art of the Deal . Trump had succeeded spectacularly in the world of Manhattan real estate. There are no waters more dark and shark infested.
As it would turn out, Trump was easy to talk to and incredibly generous. He would say yes to every single item on Dave’s list, which, by the end of the meeting, had grown to include foursomes at his Trump National Bedminster, Trump National Westchester, Trump International West Palm Beach, a day on the set of The Apprentice for four people, a dinner for six with the Donald himself at Jean-Georges, the famous Manhattan restaurant, and a $5,000 donation from Mr. Trump to Children’s National Medical Center.
Over the years, Mr. Trump has also been more than gracious to Griffin, who has grown into a healthy, grand slam–slugging fourteen-year-old golf enthusiast. Whenever the two of them see each other, they talk golf and baseball. Not many people know this, but Trump was a pretty good ballplayer himself back in high school. Sometimes during the campaign to come, Dave would hear him talk about it, usually during long rides in the car or the private airplane. But hardly ever to a crowd. Mr. Trump was also thoughtful and gracious to Dave’s girls. He knew they played tennis and one day he called Dave and said Serena Williams was going to be at Trump National to open his tennis facility. He told Dave to bring the girls.
Still, there was a point in that first meeting when Dave thought he might have ruined the whole deal.
“Steve Wynn suggested that I ask you for the golf course for free,” he said.
Trump’s benevolent smile faded.
“Oh, Steve’s a good friend,” Trump muttered finally. The real estate mogul’s eyes began to narrow. In the coming years, Dave would grow to know that look well. It was his “tough as nails” look, a New York real estate killer look. Sometimes, before Trump did interviews on shows like O’Reilly or Hannity, he’d turn to Hope Hicks or Keith Schiller, his longtime bodyguard, Jason Miller, or Corey or Dave to ask if the stare was up to par that day.
“How’s the look?” he’d say, looking straight through the camera.
But this was the first time that Dave had ever seen the iron girder stare. Behind it, he could practically see Mr. Trump imagining Steve Wynn chuckling, feet up on his desk in Sin City. He could also see Trump plotting how he was going to get even.
But just as fast as “the look” came, it disappeared. Trump explained to Dave that he had golf courses all over the world, and had friends who ran fantastic charity tournaments on just about every one of them.
“If I set a precedent with you, then how could I say no to anyone else?” he asked. “My manager wouldn’t be able to make it work. But I will do something nice for you. Don’t worry, you’ll love it.”
He then invited Dave to lunch at the Trump Grill in the atrium of Trump Tower. At the table, Trump began to take his end of the deal.
Though Dave knew the topic of politics would come up, he didn’t go to see Trump with any other motive besides making a connection for his golf tournament. In fact, he was hoping to sidestep an in-depth political discussion. Like everyone else, he knew Trump’s reputation for false political starts. Donald Trump had been considering running for president as far back as 1987, when a “Draft Trump” movement caught fire and blazed through the press. It was way back then when he gave perhaps his first political speech at a restaurant in Portsmouth, New Hampshire. His appearance packed the place and cameras televised the event. It was a harbinger of things to come.
After lunch, Trump told Dave that he would be in touch. It was a promise he kept. The day of the tournament, Dave kept his phone on in case anyone had a problem. It rang when he was playing the sixth hole. Mr. Trump wanted to know how he liked the golf course, the food, and the staff.
During 2011, Dave and Trump spoke on the phone often. In June 2011 in New Hampshire, Mitt Romney announced he was running for the presidency in 2012, and soon Trump was telling Dave that Mitt was a terrible candidate, an opinion that was widely shared among Republican political pros and, ultimately, with good old Republican voters alike. Finally, during one conversation, Dave asked the question that had been hanging in the air.
“Do you want to run?”
“I don’t know,” Trump said. “I want to, but…”
Despite Donald Trump’s past political performance, it was a substantial enough maybe for Dave to put in some work on a little exploratory operation.
“Let’s see what we come up with,” he said.
That year, Dave commissioned a poll, just to test the waters, with questions like: “Would you like to see Donald Trump get in the race?” “Do you think Donald Trump would make a good president?” and “Do we need a businessperson as president?”
When the numbers came in, they showed that Trump’s name recognition was off the charts, but Dave already knew that. They also revealed that Mr. Trump’s business credentials registered higher with prospective voters than Romney’s did. But that wasn’t such big news. What did surprise Dave was that the poll said that Trump would beat Romney head-to-head in some important primary states.
There was only one real negative, but it was a big one. The prospective voters didn’t believe he would run. Still, the poll was perhaps the first documented evidence that Donald J. Trump would be a formidable candidate for the Republican nomination.
Trump ended up endorsing Romney on February 2, 2012, from the event stage of the Trump International Hotel in Las Vegas, just a few hundred feet from the floor of Steve Wynn’s casino.
“There are some things that you can’t imagine happening in your life,” Romney said, standing next to Trump the day he received his support. “And this is one of them.”
There’s no way for us to know for sure if Mitt was trying to be sarcastic or not. If he was, he changed his tune when the endorsement began to translate to votes in Michigan, Ohio, and other prominent Republican states. Just after he endorsed Romney, during the tight final weeks of the election, Trump recorded a few robocalls—political-speak for those prerecorded phone messages that always seem to come as you’re sitting down to dinner—raving about Mitt Romney and running down some of the other candidates. Just about every night, voters in individual battleground towns would get a one-minute phone call from Donald Trump himself, all smooth and earnest and fired up about Mitt.
“I support Mitt Romney because he’s the outsider in the race,” he’d say. “He’s a good man; he’s working hard. We’ve gotta get him elected because he’s the one man who’ll beat President Obama. He will win. You’ve gotta give him that chance.”
Friendly, casual, and honest—just like the straight-to-camera Facebook monologues that’d go viral in 2016 and help him win his campaign.
Unfortunately, Mitt didn’t end up being very lucky. Yet his loss to Barack Obama in 2012 turned out to be most fortunate for the billionaire builder and Vegas casino owner who had endorsed him. In hindsight, the turn of events shouldn’t have been much of a surprise. Ask any seasoned gambler on the Strip, and they’ll tell you.
The house always wins.