What did President and real estate developer Donald Trump think about real estate developer Bill Levitt? Here is what he said about halfway through a 2017 speech at the Boy Scout Jamboree (and discussed in Edward Berenson’s Perfect Communities):

In life, in order to be successful — and you people are well on the road to success — you have to find out what makes you excited, what makes you want to get up each morning and go to work? You have to find it. If you love what you do and dedicate yourself to your work, then you will gain momentum? And look, you have to. You need the word “momentum.” You will gain that momentum. And each success will create another success. The word “momentum.”
I’ll tell you a story that’s very interesting for me. When I was young there was a man named William Levitt. You have some here. You have some in different states. Anybody ever hear of Levittown?
(APPLAUSE)
And he was a very successful man, became unbelievable — he was a home builder, became an unbelievable success, and got more and more successful. And he’d build homes, and at night he’d go to these major sites with teams of people, and he’d scour the sites for nails, and sawdust and small pieces of wood, and they cleaned the site, so when the workers came in the next morning, the sites would be spotless and clean, and he did it properly. And he did this for 20 years, and then he was offered a lot of money for his company, and he sold his company, for a tremendous amount of money, at the time especially. This is a long time ago. Sold his company for a tremendous amount of money.
And he went out and bought a big yacht, and he had a very interesting life. I won’t go any more than that, because you’re Boy Scouts so I’m not going to tell you what he did.
(CROWD CHANTING)
Should I tell you? Should I tell you?
(APPLAUSE)
You’re Boy Scouts, but you know life. You know life.
So look at you. Who would think this is the Boy Scouts, right? So he had a very, very interesting life, and the company that bought his company was a big conglomerate, and they didn’t know anything about building homes, and they didn’t know anything about picking up the nails and the sawdust and selling it, and the scraps of wood. This was a big conglomerate based in New York City.
And after about a 10-year period, there were losing a lot with it. It didn’t mean anything to them. And they couldn’t sell it. So they called William Levitt up, and they said, would you like to buy back your company, and he said, yes, I would. He so badly wanted it. He got bored with this life of yachts, and sailing, and all of the things he did in the south of France and other places. You won’t get bored, right? You know, truthfully, you’re workers. You’ll get bored too, believe me. Of course having a few good years like that isn’t so bad.
But what happened is he bought back his company, and he bought back a lot of empty land, and he worked hard at getting zoning, and he worked hard on starting to develop, and in the end he failed, and he failed badly, lost all of his money. He went personally bankrupt, and he was now much older. And I saw him at a cocktail party. And it was very sad because the hottest people in New York were at this party. It was the party of Steve Ross — Steve Ross, who was one of the great people. He came up and discovered, really founded Time Warner, and he was a great guy. He had a lot of successful people at the party.
And I was doing well, so I got invited to the party. I was very young. And I go in, but I’m in the real estate business, and I see a hundred people, some of whom I recognize, and they’re big in the entertainment business.
And I see sitting in the corner was a little old man who was all by himself. Nobody was talking to him. I immediately recognized that that man was the once great William Levitt, of Levittown, and I immediately went over. I wanted to talk to him more than the Hollywood, show business, communications people.
So I went over and talked to him, and I said, “Mr. Levitt, I’m Donald Trump.” He said, “I know.” I said, “Mr. Levitt, how are you doing?” He goes, “Not well, not well at all.” And I knew that. But he said, “Not well at all.” And he explained what was happening and how bad it’s been and how hard it’s been. And I said, “What exactly happened? Why did this happen to you? You’re one of the greats ever in our industry. Why did this happen to you?”
And he said, “Donald, I lost my momentum. I lost my momentum.” A word you never hear when you’re talking about success when some of these guys that never made 10 cents, they’re on television giving you things about how you’re going to be successful, and the only thing they ever did was a book and a tape. But I tell you — I’ll tell you, it was very sad, and I never forgot that moment.
And I thought about it, and it’s exactly true. He lost his momentum, meaning he took this period of time off, long, years, and then when he got back, he didn’t have that same momentum.
In life, I always tell this to people, you have to know whether or not you continue to have the momentum. And if you don’t have it, that’s OK. Because you’re going to go on, and you’re going to learn and you’re going to do things that are great. But you have to know about the word “momentum.”
But the big thing, never quit, never give up; do something you love.

The moral of the story seems to be about momentum: Trump says Levitt once had it and then he didn’t. The Levittowns were built and Levitt was well known but then his later projects and efforts did not go as well.

Three things strike me about this story. First, is this what is expected of hot shot or important developers? Berenson describes how Levitt funded many of his projects. The selling of homes in the first section or subdivisions in communities then funded later houses. If sales slowed, the project lagged. If sales were brisk – and they were particularly quick in the 1950s – then the project could flow along. Donald Trump also leverages previous assets to fund projects. Perhaps this is just the game is played in real estate but it might not be the way many average Americans operate.

Second, Berenson details the yachting/wealthy life Levitt lived. Levitt at one point had the third biggest yacht in the world. He and his wife entertained at some of the hottest social spots. This brings him into contact with numerous famous people. This includes people like Donald Trump – a younger developer – and politicians – like Joe Biden. He did this all with relatively little real wealth; his money was tied up and not really growing. When the money started running out, he did not have many options.

Third, what counts as positive or negative momentum? This particular story is told in such a way that there is a clear rise and fall: Levitt made it to the top and then dropped to the bottom. Most lives or careers may not fit this simple structure. People and businesses face obstacles, make progress, take a step forward and a step back. How many people could even somewhat closely fit a story of only positive momentum or only upward progress?