When it comes to Donald J. Trump, there’s no shortage of opinions on what kind of businessman he is. Some see him as a larger-than-life dealmaker who can do no wrong, while others know the actual, less shiny truth. So, let’s take a clear-eyed look at some of Trump’s most glaring business failures—without the glitz, just the facts. And I promise, I’ll try to keep the sarcasm at bay.
1. Bankruptcies Galore
When people talk about Trump’s “business acumen,” it’s hard not to think about the time (or five) he declared bankruptcy. Let’s break it down:
- Trump Taj Mahal (1991): His “Eighth Wonder of the World” went under just a year after its grand opening, crushed by debt and poor financial decisions.
- Trump Castle and Trump Plaza (1992): In the same year, these Atlantic City casinos couldn’t handle their debt either and crumbled into bankruptcy.
- Trump Hotels and Casino Resorts (2004): You’d think the lesson would stick after three times, but nope—Trump’s casino empire filed for Chapter 11 again.
- Trump Entertainment Resorts (2009): The cherry on top of a consistent losing streak. Bankruptcy one last time, proving that when it comes to financial distress, Trump’s got that on lock.
2. Not Paying the People Who Did the Work
A staple in the Trump business playbook seems to be: contract work, use it, then find every loophole not to pay for it. Hundreds of contractors—everyone from painters to small-business owners—claimed Trump stiffed them on payments. He’s even been sued for it. Talk about supporting the working class, right?
3. Racial Discrimination in Real Estate
Trump’s not-so-golden years began with a lawsuit in 1973 when the Department of Justice sued his company for racial discrimination in renting practices. The evidence? Applications from Black prospective tenants were marked with a “C” for “colored.” The company settled without admitting guilt but agreed to change practices. Not exactly the hero of equal opportunity housing.
4. The Graveyard of Trump Business Ventures
- Trump University: A masterclass in scams, not real estate. Multiple lawsuits, a $25 million settlement, and a lot of people who felt duped by promises that were as empty as an abandoned ballroom.
- Trump Steaks: Because who doesn’t want overpriced meat from a real estate mogul? Spoiler: Almost everyone. The product tanked.
- Trump Vodka: Marketed as “Success Distilled.” The irony? The company stopped distilling it after just a few years due to poor sales. So, cheers to that failure.
- Trump Airlines: A vanity project that bled money until creditors took over. The “luxury” was short-lived.
- GoTrump.com: An attempt to corner the travel website market that promptly fell flat. Competing with Expedia and Orbitz is hard when you’re only offering a name and not much else.
5. Subpar Products
Whether it was Trump Ice (a bottled water that failed to make waves) or Trump: The Game (which, ironically, didn’t sell well), the track record for successful products bearing the Trump brand is bleak. Let’s just say the “quality” often wasn’t worth the premium price.
6. Charitable Shenanigans
The Trump Foundation was found to be a personal piggy bank disguised as charity. The New York Attorney General cited Trump for using the foundation’s funds for self-serving purposes, including settling lawsuits and making campaign donations. The foundation was dissolved, and Trump was ordered to pay $2 million. Philanthropy, indeed.
7. Debt, Debt, and More Debt
Trump’s entire business empire has often been propped up by immense debt. The kind that gets you high credit leverage but brings a business to its knees when the bills come due. Repeated bankruptcies and defaults didn’t do much to strengthen his credit score, either.
8. Fleeting International Ventures
Trump’s brand licensing agreements abroad also had their share of problems. From failed projects in places like India to politically controversial towers in Turkey, Trump’s global business dealings have been marred with issues that range from questionable partnerships to corruption scandals.
9. Tax Records That Say It All
Years of investigative reporting have shown that Trump paid very little in federal income taxes. His tax records revealed huge business losses that undercut his carefully curated image as a financial genius. He once famously said, “That makes me smart.” Sure, it also makes it clear how messy his finances really are.
10. Aggressive (and Questionable) Business Practices
Trump wasn’t above employing aggressive tactics, including lawsuits, to get his way. He’d sue critics, contractors, and even governments if it helped him save face or avoid accountability. Not to mention, marketing hyperbole and misleading statements were staples of his business model, leaving many consumers disappointed.
So, tell me again how Donald J. Trump is good for business when he can’t even successfully or ethically run his own?
Also, if you’ve been digging my work on here, and want to see me be able to continue writing as close to full-time as humanly possible, please take a look at my Patreon page at www.patreon.com/mjdistefano. Even $1 a month helps bigly!
Ad-Free & Subscriber Log-In