I was triggered this morning by an article by constitutional lawyer and Trump apologist Jonathan Turley, who plies his wares on Fox News and several media outlets, generally pointing his followers to which Democrats to condemn. He’ll find the wildest statement of an obscure Democrat and attribute those beliefs to the entire Party. He’s written multiple articles about the Democratic Socialists of America (DSA) that make up .003% of the Democratic Party that imply all Democrats conform to their ideology. Today, he published an article, “From Influence Peddler to Starving Artist: Hunter Biden Claims Family is Broke in Defaulting on $17 Million Bill.”
The subject is fair game, but not without mention or comparison to Donald Trump, who has stiffed attorneys and contractors for decades, who will never get reparations from the $1,776 billion slush fund that didn’t die, or the billions Trump and family members have coerced from Mideast investors and writing a favorable crypto policy. It’s common knowledge that Trump has a trail of unpaid bills. I’ve not seen them compiled and totaled to get a sense of how he’s stiffed people over the years. Many unpaid debts have not been made public because you can’t win a spitting contest against someone willing to do or say anything, along with turning his hordes of followers against you. He’s also the sitting president who has multiple ways to harm you and isn’t afraid to use them.
I’ll probably come up with some additional categories while I write, but Trump is infamous for failing to pay attorneys who have represented him over the years, similar to the Hunter Biden situation Turley wrote about. Here’s a woefully incomplete list of lawyers Trump has failed to pay and apparently has no intention of ever doing so.
Attorney Fees
| Law Firm | Approx. Amount Owed | Jurisdiction / Location | Context |
| NechelesLaw LLP | >$660,000 | New York, USA | Criminal defense; Stormy Daniels hush-money case |
| Wharton Law PLLC | ~$112,000 | New York, USA | Criminal defense in hush-money trial |
| Sullivan & Cromwell LLP | ~$400,000 | New York, USA | Appeals work in hush-money and related cases |
| James Otis Law Group LLC | ~$1,700 | St. Louis, Missouri | Litigation; lawyer later nominated to federal judgeship |
| Brito PLLC | >$44,000 | Florida, USA | Defamation suits vs. media; $5B JPMorgan case |
| Habba Madaio & Associates LLP | ~$19,000 | New Jersey, USA | Civil litigation; firm near Bedminster golf course |
| William Sturges LLP | ~$27,000 | London, UK | Partner-led commercial legal services |
| Level Law LTD | ~$20,000 | London, UK | White-collar / commercial legal services |
| Secil Law PLLC | (amount not disclosed) | USA | White-collar criminal defense |
| Tacopina, Seigel & DeOreo | (amount not disclosed) | New York, USA | Criminal defense firm |
| Weber, Crabb & Wein, P.A. | (amount not disclosed) | Florida, USA | Florida litigation firm |
| Other firms (paid, no current debt) | $0 outstanding | Various | Ostergren; Dhillon; Elections LLC; Epstein & Co.; Farris, Parker & Hubbard; New Age Consulting; Richard C. Klugh; Binnall Law Group |
Trump, the Trump Organization, and his campaigns have decades of disputes with lawyers, contractors, and vendors — many resolved, many sealed, many only partially documented. Public reporting shows patterns but not a single authoritative ledger of all unpaid or underpaid parties and their amounts. Some firms not named received court-ordered fee payments far below their normal billing rates in Trump’s six corporate bankruptcies.
Contractors
All business isn’t good business, as many contractors have discovered after getting contracts from Donald Trump. Here’s a partial list of firms that were once excited to have gotten Donald’s business, only to learn the hard way he doesn’t always pay. Some of these debts were settled for cents on the dollar, which is the Trump business model:
| Contractor / Firm | Amount Claimed Owed | Project / Context | Source Notes |
| AES / Freestate Electrical | $2,075,731.61 | Electrical work on Trump International Hotel (D.C.) | Contractor says Trump Org paid $15.13M but left $2.075M unpaid. Other contractors on same project claimed ~$5M collectively. |
| Edward Friel Cabinetry (PA) | $83,600 | Cabinetry for Trump Plaza, Atlantic City | Final invoice allegedly unpaid; contract value was ~$400,000. |
| The Paint Spot (Juan Carlos Enriquez) | ~$30,000 judgment | Painting work at Trump National Doral (Miami) | Won judgment; judge ordered foreclosure to enforce payment. |
| Walters (fabric vendor) | ~$380,000 shortfall (claimed ~$1.2M; settled for $823,000) | Fabric contract dispute | Vendor said he was owed ~$1.2M; accepted $823k settlement. |
| Forest Jenkins (contractor) | Contract: $200,000 (unpaid amount not specified) | Taj Mahal casino project | Reporting notes contract award; unpaid balance not publicly documented. |
| Trump Mortgage case (real estate broker) | $298,274 judgment | Trump Mortgage | Judge ordered Trump Mortgage to pay $298,274. |
| Hardy v. Kaszycki & Sons (class action) | $1,375,000 settlement | 1980s demolition/construction work | Settlement disclosed in late 1990s. |
| Various Atlantic City contractors | ~$70,000,000 total (253 contractors) | Trump Taj Mahal | Reporting cites $70M owed to 253 contractors. |
| Trump International Hotel (D.C.) liens | >$5,000,000 total | Construction liens | Multiple firms filed liens for unpaid work. |
| Small worker/contractor suits | ~$800 average per worker | Trump National Doral (Miami) overtime cases | Dozens of workers settled for small amounts. |
| Construction trust litigation | $12,000–$104,000 | Various subcontractor disputes | Range of claims documented in court records. |
Banks
Trump often “renegotiates deals.” If you’ve followed any Trump negotiation, details are often flexible but not in a good way. A Trump bank loan is renegotiated every time he gets into financial trouble, which has happened often.
In the 1990s, Trump restructured loans on the Taj Mahal, Plaza Hotel, and Trump Castle in Chapter 11 bankruptcy deals. Creditors took equity because Trump’s businesses could not meet payment terms. These were bondholder and lender syndicate restructurings, not individual bank workouts. Here’s how the banks made out, sometimes experiencing historic losses.
| Trump Business (Chapter 11) | Year | Who Lost Money | What Happened | Source Notes |
| Trump Taj Mahal | 1991 | Bondholders, lenders | Trump missed debt payments within a year; creditors took ~50% equity and wrote down debt | Reporting confirms missed payments and creditor-for-equity swap. |
| Trump Plaza Hotel | 1992 | Lender group (six major lenders) | Trump could not service high-interest debt; lenders took ~49% ownership and restructured terms | Documented as a major lender loss and ownership transfer. |
| Trump Castle | 1992 | Bondholders, secured lenders | Trump unable to meet bond obligations; creditors took equity and restructured debt | Reporting confirms repeated inability to meet terms. |
| Trump Hotels & Casino Resorts | 2004 | Bondholders, institutional lenders | Company filed Chapter 11; creditors accepted reduced repayment and restructured debt | Part of long-running casino debt failures. |
| Trump Entertainment Resorts | 2009 | Lenders, bondholders | Another Chapter 11; creditors wrote down debt and took control | Continuation of casino losses. |
American Cities after Trump Campaign Rallies
During the three Donald Trump presidential campaigns, Trump went from place to place, drawing large crowds while requiring massive local expenses his campaigns were supposed to cover. They didn’t. Here’s a list of what Trump still owes to the cities he said he’d make great again. This doesn’t include losses like those incurred in Florida, such as Florida’s short-lived Alligator Alcatraz, currently estimated at $218 million.
| City / County | Amount Owed | Year(s) of Event | Status Reported by City | Notes |
| El Paso, Texas | ~$570,000 | 2019–2020 | Unpaid; city hired outside counsel | Rally security, police overtime, traffic control |
| Albuquerque/Rio Rancho, NM | $444,986 | 2019 | Unpaid; interest added over years | Santa Ana Star Center rally; invoice doubled with fees |
| Erie, Pennsylvania | >$40,000 | 2018, 2023 | Unpaid | Police, traffic, EMS costs |
| Mesa, Arizona | $65,000 | 2018 | Unpaid | Barricades, towing, crowd control |
| Missoula County, Montana | ~$13,000 | 2018 | Unpaid | Law enforcement overtime |
| Ten additional cities (Center for Public Integrity review) | $841,000+ total | Various | Unpaid | CPI identified unpaid municipal invoices but did not list each city publicly |
Other Categories of People & Businesses Who Lost Money Dealing With Donald Trump
| Category | How They Lost Money | Examples / Notes |
| — — — — — | — — — — — — — — — — — | — — — — — — — — — |
| Bondholders | Took massive losses in Chapter 11 restructurings; accepted equity instead of repayment | Taj Mahal bondholders lost millions; Plaza Hotel bondholders took ownership stakes instead of full repayment |
| Shareholders (public company investors) | Trump Hotels & Casino Resorts stock collapsed; repeated losses before delisting | Investors lost value as the company filed bankruptcy multiple times |
| Employees | Unpaid wages, overtime disputes, sudden layoffs during casino collapses | Doral workers won small settlements; Atlantic City casino closures left thousands unpaid or underpaid |
| Small vendors & suppliers | Unpaid invoices, partial settlements, liens | Fabric suppliers, food vendors, small tradespeople across multiple Trump properties |
| Local governments / municipalities | Unpaid rally bills, police overtime, venue costs | El Paso, Albuquerque/Rio Rancho, Erie, Mesa, Missoula County, plus 10 other cities identified in CPI review |
| Taxing authorities | Trump entities negotiated reduced tax liabilities or failed to pay on time | Atlantic City tax disputes; negotiated reductions after casino failures |
| Business partners & co‑investors | Lost capital when Trump projects underperformed or entered bankruptcy | Plaza Hotel partners; casino joint‑venture partners |
| Casino regulators & state agencies | Lost licensing fees, oversight costs, and tax revenue due to repeated bankruptcies | New Jersey regulators documented millions in lost revenue during casino failures |
| Charities | Trump Foundation misused funds; settlements required repayment | NY Attorney General settlement dissolved the foundation; donors and beneficiaries lost intended funds |
| Students / consumers | Trump University settlements for deceptive practices | $25 million settlement paid to students who lost money |
| Campaign vendors | Unpaid bills for event services, security, staging, printing | Numerous small vendors reported unpaid or partially paid invoices |
| Political committees (internal) | PACs drained by legal fees, leaving debts to vendors | Save America PAC owes >$1.6M to law firms |
Investors
Trump ventures have failed so often and so spectacularly that it’s impossible to say how any individual investor might have done. “Let the buyer beware” definitely applied for anyone thinking they’d get rich on Trump Steaks or Trump Wine. Trump University was a fraud, as was his charity. I will focus on two recent opportunities to make money with Donald Trump: Truth Social (DJT) and World Liberty (WLDS). Generally speaking, retail investors were hammered. Insiders were not.
Truth Social collapsed from its highs. DJT closed at $8.77 on May 12, 2026, down 77.47% from its March 1, 2024 price of $38.94. Over the past year, the stock shed 64.12%. The all‑time high was $97.54 (March 4, 2022)—current price: $9.86. Anyone who bought near the hype peaks lost 60–80% of their money. This isn’t a case of Trump failing to pay money owed, but of overpromising and structuring a deal where he made money while investors were taken for theirs.
World Liberty’s investors ended up in the same familiar position as the retail crowd in Truth Social: holding the bag while insiders walked away untouched. The average WLDS investor bought into a SPAC that never delivered the promised deal flow, watched the share price collapse after the hype evaporated, and absorbed nearly all the losses. Meanwhile, Patrick Orlando and other insiders — who received their founder shares for pennies — were insulated from the downside. It was the same structural imbalance seen in Trump‑aligned ventures: insiders entered at negligible cost, exited with disproportionate upside, and left everyday investors with a deflated asset and no meaningful recourse. In both cases, the “brand premium” enriched the people at the top and punished the people who believed the pitch. World Liberty Financial token sales generated over $1.4 billion. Trump and his family personally collected 75% of that revenue.
I didn’t come close to meeting my original objective of documenting all of Trump’s unpaid bills or the extent to which he left his investors in the lurch. I do know that whatever Hunter Biden owes pales in comparison to the bills Donald Trump left behind, let alone the debt Trump owes to the American people. In the end, the list of people Trump owes isn’t a list at all; it’s a business model. For forty years, the pattern has stayed the same: Trump takes the upside, and everyone else eats the loss. Contractors, attorneys, banks, bondholders, cities, investors — the names change, but the outcome doesn’t. The debts linger, the bills go unpaid, and the people who believed the pitch are left holding the bag. Trump doesn’t escape his obligations because he’s brilliant; he escapes them because someone else always pays.