Trump’s Playbook in Practice: A Timeline of Consequences

When people stand to defend Donald Trump’s behavior—whether in business, in court, or in the White House—they often reach for the same source: The Art of the Deal, his bestselling book from the 1980s.

They quote it like it’s proof of genius—as if referencing a line from The Art of the Deal turns every reckless decision into a masterstroke, and every critic into someone who “just doesn’t get it.” The message behind the quote is often the same: this isn’t failure or corruption—it’s strategy you’re too ordinary to understand. Ruthless manipulation gets recast as brilliance. And questioning it? That just proves you’re not in on the game.

One of their favorite lines?

“If you don’t have leverage, create it.”
 

At first glance, that might sound clever—even strategic. But when I looked closer at how Trump has actually used leverage throughout his life, I started to see a pattern. Not of strength, but of manipulation. Not of leadership, but of self-preservation at any cost.

And here’s something they rarely mention: The Art of the Deal was ghostwritten by journalist Tony Schwartz—who has since publicly disavowed the book. Schwartz now calls it a dangerous myth and has said he regrets helping to build the persona that Trump rode into power.

So I decided to put the outcomes on display.

Below is a timeline that compares Trump’s most well-known claims—many of them straight from The Art of the Deal—with the outcomes that followed. It includes bankruptcies, court rulings, impeachments, failed ventures, and criminal charges. It shows how a brand built on boldness and success often hid recklessness, deception, and harm.

This isn’t about political rivalry. It’s about truth.

If we’re going to quote a book to justify someone’s rise to power, we should also look at how well that book holds up when tested by reality.