Trump: The Art of the Deal in 5 Minutes

Updated: Feb 21, 2020

In 1987, at arguably the high-point of his business career, Donald Trump and ghost-writer Tony Schwartz wrote Trump: The Art of the Deal. This mostly autobiography and somewhat business advice book rose to become #1 on the New York Time’s Best Seller list, and eventually paved the way for Trump's respectable side-career as a ‘business section’ staple author. While not quite living up to Trump’s claims as ‘the best-selling book of all-time’, it is safe to say that The Art of The Deal is one of the 10 best-selling business biography books of all-time.

In case you either never read the book or don’t want to commit the time and effort to it, here’s a quick 5-minute summary of the book's structure, 11 Trump Cards (pieces of advice), and the 10 deals discussed throughout.

Book Structure

Trump: The Art of the Deal is written in 14 Chapters. Here’s how the book is laid out:

  • Chapter 1 depicts a “week in the life” of Donald Trump, where Schwartz documents every minute of Trump’s day for 5 straight days.

  • Chapter 2 is where Trump describes his 11 ‘Trump Cards’ for business success.

  • Chapter 3 is the customary story of Trump’s early life and upbringing.

  • Chapters 4 – 13 are chronologically organized into short stories of each significant business deal Trump had worked on in his career to-date.

  • Chapter 14 is the final chapter in the book, where Trump reviews and concludes his Chapter 1 “week in the life”.

11 Trump Cards

In Chapter 2, Trump offers 11 pieces of advice (‘Trump Cards’) for success in business and real estate:

1. Think Big

  • If you’re going to be thinking anyway, you might as well think big. Most people think small, because most people are afraid of success, afraid of making decisions, afraid of winning. And that gives people like me a great advantage.”

  • “One of the keys to thinking big is total focus. I think of it almost as a controlled neurosis, which is a quality I’ve noticed in many highly successful entrepreneurs. They’re obsessive, they’re driven, they’re single-minded and somethings they’re almost maniacal, but it’s all channelled into their work.”

2. Protect the Downside and the Upside Will Take Care of Itself

  • I believe in the power of negative thinking. I happen to be very conservative in business. I always go int the deal anticipating the worst. If you plan for the worst – if you can live with the worst – the good will always take care of itself.”

3. Maximize Your Options

  • “I never get too attached to one deal or one approach. For starters, I keep a lot of balls in the air, because most deals fall out, no matter how promising they seem at first. In addition, once I’ve made a deal, I always come up with at least a half dozen approaches to making it work, because anything can happen, even to the best-laid plans”

4. Know Your Market

  • “I do my own surveys and draw my own conclusions. I’m a great believer in asking everyone for an opinion before I make a decision.”

5. Use Your Leverage

  • “The worst thing you can possibly do in a deal is seem desperate to make it. The best thing you can do is deal from strength, and leverage is the biggest strength you can have. Leverage is having something the other guy wants. Or better yet, needs. Or best of all, simply can’t do without. Unfortunately, that isn’t always the case, which is why leverage often requires imagination, and salesmanship. In other words, you have to convince the other guy it’s in his interest to make the deal.”

6. Enhance Your Location

  • “You don’t necessarily need the best location. What you need is the best deal. Just as you can create leverage, you can enhance a location, through promotion and through psychology.”

  • “What you should never do is pay too much, even if that means walking away from a very good site.”

7. Get The Word Out

  • “I play to people’s fantasies. People may not always think big themselves, but they can still get very excited by those who do. That’s why a little hyperbole never hurts. People want to believe that something is the biggest and the greatest and the most spectacular. I call it truthful hyperbole. It’s an innocent form of exaggeration – and a very effective form of promotion.”

8. Fight Back

  • “I’m very good to people who are good to me. But when people treat me badly or unfairly or try to take advantage of me, my general attitude, all my life, has been to fight back very hard.”

  • “My experience is that if you’re fighting for something you believe in – even if it means alienating some people along the way – things usually work out for the best in the end.”

9. Deliver The Goods

  • “You can create excitement, you can do wonderful promotion and get all kinds of press, and you can throw in a little hyperbole. But if you don’t deliver the goods, people will eventually catch on.”

10. Contain The Costs

  • “You can dream great dreams, but they’ll never amount to much if you can’t turn them into reality at a reasonable cost”.

  • “I learned from my father that every penny counts, because before too long your pennies turn into dollars.”

11. Have Fun

  • “Money was never a big motivation for me, except as a way to keep score. The real excitement is playing the game.”

“My style of deal-making is quite simple and straightforward. I aim very high, and the I just keep pushing and pushing and pushing to get what I'm after. Sometimes I settle for less than I sought, but in most cases I still end up with what I want.” -Donald Trump

Trump’s Deals

The majority of the book is dedicated to a first-hand description of 10 investment deals that Trump had either completed, or was currently in the process of making, at the time of the book’s publishing. In retrospect, it’s quite interesting to see that the ‘iconic dealmaker’ is actually not much better than a flip of a coin.

Trump's 10 Deals

Swifton Village (Cincinnati, Ohio)

Success: This was Trump’s first deal. He and his father purchased the condominium complex in the late 1960s and eventually sold the complex for a ~$6 million profit.

Westside Yards (Part 1)

Neutral: Trump let his purchase option expire (with no monetary gain/loss).

The Commodore Hotel – The Grand Hyatt

Success: The redevelopment of The Commodore Hotel into The Grand Hyatt New York was a transformational project for the Grand Central Station neighborhood in Manhattan and netted Trump $140 million in his eventual sale.

Trump Tower

Success: Trump Tower was a resounding commercial success and still stands as an iconic building in New York City today.

Holiday Inn – Trump Plaza Hotel & Casino

Failure: In 1992, Trump Plaza Hotel & Casino filed for a prepackaged bankruptcy as casino revenues fell sharply. Ownership was eventually transferred to his publicly traded company, Trump Hotels & Casino Resorts, but after years of losses the casino was permanently closed in 2014.

Trump’s Castle

Failure: In 1991 when Trump’s Castle failed to meet its debt obligations, Trump’s Castle underwent a debt restructuring program that was filed as a prepackaged bankruptcy. Trump later regained control and sold his stake to his publicly traded company, Trump Hotels & Casino Resorts, and the casino subsequently filed for bankruptcy in the late 90s following multiple changes in ownership.

100 Central Park South & The Barbizon Plaza Hotel – Trump Parc

Success: Trump successfully converted these two buildings, one a former hotel and the other a former rent-controlled apartment complex, to condominiums in 1988. The conversion was considered a financial success for Trump who sold the new condominium units for a significant premium over the $65 million he purchased the buildings for.

United States Football League (USFL)

Failure: The USFL went bankrupt shortly after the writing of the book. The investment was a total loss.

Wollman Rink

Neutral: This was a non-profit deal for New York City for which Trump took over construction after years of government delays.

Westside Yards (Part 2) – Television City

Failure: Amidst significant public opposition, Trump’s Television City was never developed as planned. In order to proceed with the project, Trump sold the controlling interest in the development, the scale of the plan was significantly reduced, and construction only commenced in 1997 with parts of the project still under construction as of 2019.

Trump's 10 Deals Broken Down By Success & Failure