After signing the Epstein Files Transparency Act, the Trump administration's DOJ missed legal deadlines, secretly re-redacted files, and withheld documents containing allegations that Trump sexually abused a minor — prompting a UN finding that the crimes described may amount to crimes against humanity, bipartisan congressional subpoenas of AG Bondi, and calls for a special counsel over alleged perjury.
DOGE employees at SSA secretly worked with a political advocacy group to match Social Security data with voter rolls to find 'evidence of voter fraud and to overturn election results.' A signed data-sharing agreement and Hatch Act referrals followed. A whistleblower alleged DOGE copied 300+ million Americans' records into an unsecured virtual database.
The deputization of Musk's private bodyguards as federal agents — with training requirements waived at White House request — represents an unprecedented merger of private security with federal law enforcement authority, bypassing the safeguards that exist to prevent untrained armed individuals from exercising government power.
Musk used his government role leading DOGE to dismantle the CFPB, the agency positioned to regulate his XMoney digital payments platform, while gaining access to competitors' confidential financial data — a textbook conflict of interest that multiple ethics bodies have flagged as potentially criminal.
DOGE accessed Treasury, OPM, and SSA databases containing millions of Americans' personal data without authorization or completed background checks. Federal judges ordered data disgorged and deleted, finding Privacy Act and APA violations, though the Supreme Court later partially reversed.
DOGE associates including Tom Krause (Broadcom executive) and Marko Elez (25-year-old with racist posts) accessed Treasury's $6 trillion payment system. Elez was mistakenly given write access to payment records. 19 AGs sued. A federal judge blocked access, calling it 'chaotic and haphazard,' but the 4th Circuit later reversed.
The world's richest man led government cost-cutting while his companies held $38 billion in government funding. Zero Musk contracts were cut. SpaceX won new billions in Pentagon contracts during the cuts. No ethics forms were filed.
A systematic pattern of pardons benefiting political allies, donors, and financial criminals. Over half of 88 clemency grants went to white-collar offenders, erasing $1.3 billion in victim restitution. Twenty corrupt politicians were pardoned. The DOJ's Public Integrity Section — responsible for investigating corruption — has been largely dismantled, and the head of the Pardon Attorney's office was fired and replaced with a political loyalist.
An unprecedented pattern of foreign government payments flowing to the president's personal businesses and financial ventures, including real estate deals in Vietnam, Serbia, Saudi Arabia, and the Gulf states, the LIV Golf partnership, a $400 million Qatari jet, and cryptocurrency schemes — prompting multiple Senate resolutions condemning the arrangements as Emoluments Clause violations.
Judge Engoron found that Trump had consistently and intentionally misrepresented asset values across a decade of financial statements. His Mar-a-Lago estate was valued in financial statements at up to $739 million — despite its deed restricting it to residential use, with an estimated fair market value of $75-100 million. His Trump Tower triplex was listed at 30,000 square feet when it was actually 10,996 square feet — nearly three times its actual size. The fraud allowed Trump to obtain loans at more favorable rates than he would have received with accurate valuations.
Weisselberg, the Trump Organization's CFO for decades, had pleaded guilty in August 2022 to 15 felony counts and agreed to cooperate with prosecutors. He testified against the company. The Trump Organization received $1.76 million in off-the-books compensation for Weisselberg and other executives over 15 years. The company was convicted on all 17 counts, including scheme to defraud and falsifying business records. The $1.6 million fine was the maximum allowed but was a fraction of what corporate criminal fines typically run; prosecutors noted the fine was limited by statute.
Trump issued 143 pardons and commutations, including a final batch of 143 on his last day in office. Analysts documented that a disproportionate share of Trump's pardons went to political allies, relatives of political allies, or individuals whose cases were connected to Trump's political interests. The pardons of Manafort, Stone, Flynn, and Bannon were specifically notable because each had been convicted or charged in connection with conduct related to Trump's political activities, and each received executive clemency. The final day pardons also included Steve Bannon, who was awaiting trial.
Kushner had 40 contacts with foreign nationals from more than 20 countries that he failed to disclose on his original security clearance form — submitting three amended versions before all contacts were documented. Career security officials recommended denying or limiting Kushner's clearance; Trump overruled them in May 2018. A White House personnel security director told a congressional committee that she had been pressured to grant the clearance against her professional judgment. Both Trump and Ivanka publicly denied Trump had intervened, before the New York Times reported he had personally ordered the clearance.
Manafort received over $65 million to manage political campaigns for Viktor Yanukovych, the pro-Russian Ukrainian president later forced from office and who fled to Russia. Manafort hid the income in offshore accounts and spent lavishly while lying on tax returns and bank loan applications. Mueller's investigation documented that Manafort had also shared internal Trump campaign polling data with Konstantin Kilimnik, a Ukrainian political consultant assessed by the U.S. Senate to have ties to Russian intelligence — data sharing that occurred during the period when Russia was conducting its interference operation.
Kushner's initial SF-86 security clearance form, filed in January 2017, omitted more than 100 foreign contacts, including meetings with Russian ambassador Sergey Kislyak and Russian banker Sergey Gorkov. He amended the form multiple times. Career intelligence and law enforcement officials raised concerns about his business's financial entanglements with foreign nationals, including a $1.4 billion loan his family company received from Qatari-linked investors, and meetings he had had with foreign officials during the transition. Chief of Staff John Kelly wrote an internal memo stating he personally overruled the career professionals' recommendation against granting clearance. Trump later denied to journalists that he had ordered the clearance, contradicting Kelly's memo.
The ProPublica investigation documented a 'shadow VA' in which the three Mar-a-Lago members — who paid $200,000 entry fees — exchanged hundreds of calls and emails with VA officials, reviewed candidates for top positions, influenced multimillion-dollar contract decisions including a $10 billion electronic health records contract, and shaped the VA's strategic direction without any official appointment. VA Secretary Shulkin had cooperated with the arrangements. He was fired amid internal feuding; Trump nominated his personal physician Ronny Jackson as replacement; Jackson withdrew after Senate investigators documented allegations of drunk driving, overprescribing, and creating a 'toxic work environment.'
The State Department IG's report, released in September 2020, found that Pompeo had used department staff and resources for personal and political purposes in violation of federal regulations. Staff described being directed to walk Pompeo's dog, pick up his dry cleaning, make restaurant reservations, and run other personal errands. Susan Pompeo, who had an official role as diplomatic spouse, used State Department resources for what the IG characterized as non-official events. At least 17 dinners charged to the State Department were found to include politically-oriented guests or personal guests rather than serving diplomatic purposes. Pompeo had fired IG Steve Linick in May 2020; Linick said the firing was retaliation for the investigation. Pompeo denied wrongdoing.
Trump's Section 232 and Section 301 tariffs disrupted U.S. trade relationships with allies and adversaries alike. The steel and aluminum tariffs targeted Canada, the EU, Japan, and South Korea — treaty allies — under a national security designation that even many Republicans criticized as pretextual. Retaliatory tariffs by China on soybeans, pork, and other agricultural goods caused severe damage to American farmers, requiring $28 billion in emergency agricultural assistance.
The TCJA was passed through the budget reconciliation process with no Democratic votes; the process required the individual tax cuts to expire (via budget rules) while making the corporate rate cut permanent. Trump claimed the cut would generate economic growth sufficient to pay for itself — a prediction rejected by the CBO, the JCT, and most economists. The $1.9 trillion corporate stock buyback surge in 2018 documented that the primary immediate effect was share buybacks rather than business investment or wage growth. The Trump family directly benefited from the pass-through deduction. Trump signed it into law and called it 'one of the great Christmas gifts to middle-income people.'
The $31,561 dining set — table, chairs, and hutch — was ordered in September 2017 for Carson's HUD suite. A career HUD employee, Helen Foster, filed a complaint alleging she was reassigned after she raised concerns about the legality of the purchase. Foster said she was told by HUD leadership that the order would go forward and that 'someone' had ordered it who outranked her. After the purchase became public in February 2018, Carson and his wife initially disputed involvement; subsequent reporting found text messages showing his wife Candy Carson personally directed the purchase and selected items. Carson reimbursed HUD and the set was canceled. The HUD inspector general investigated.
The government plane honeymoon request was denied after it became public in August 2017. Mnuchin said he had made the request for security reasons and had not been aware of the cost. The Kentucky solar eclipse trip drew IG scrutiny when reports emerged that Linton had asked whether she could accompany Mnuchin on the official trip specifically to watch the eclipse. The IG found the trip had a legitimate official purpose — Mnuchin was scheduled to attend meetings at the Fort Knox federal reserve — but noted concerns about the process and the optics of combining official travel with personal viewing of the solar eclipse. Linton's Instagram post — she tagged designer brands she was wearing and responded hostilely to a commenter — became a symbol of administration attitudes toward wealth and public service.
Price's private jet use was revealed by Politico, which reported in September 2017 that he had taken multiple private charter flights at costs far exceeding commercial alternatives — including a $25,000 flight from Washington, D.C. to Philadelphia, a route served by Amtrak trains for under $80 and commercial flights for under $200. After the initial Politico report, additional flights were disclosed including trips to Europe, Africa, and Asia on military aircraft. Trump initially said he was 'not happy' about the reports while keeping Price in office, then accepted Price's resignation on September 29, 2017. Price offered to reimburse approximately $52,000 — the cost of his seat only on the flights — but not the full charter costs.
Zinke used government aircraft for personal travel, including a trip to attend a hockey game and a flight to meet a donor. He pursued a real estate development near his Montana property with a company connected to Halliburton CEO David Lesar — while Halliburton had business before the Interior Department. He intervened in tribal gaming compacts in Connecticut to benefit a political donor's competing casino operation. He reduced Bears Ears National Monument by 85% and Grand Staircase-Escalante by nearly half — the largest rollback of protected federal land in U.S. history. He resigned in December 2018; the DOJ referred his conduct for further investigation.
Pruitt's tenure combined serious corruption with aggressive deregulation — two goals that reinforced each other. His 24/7 security detail, which EPA Inspector General reports found was not justified by credible threats, cost taxpayers approximately $3.5 million in his 17 months at the agency. He flew first-class on domestic flights, claiming security concerns, while his own security detail said coach was adequate. He rented a condo from the wife of a lobbyist — at $50/night — while her clients' matters were pending before the EPA. He granted unprecedented raises to two staff members through CAA authority after the White House had denied the raises. He was ultimately undone by the accumulation of scandal but had already implemented dozens of deregulatory actions.
Trump retained ownership of his business empire throughout his presidency, rejecting the divestment that every modern president had undertaken. The Trump International Hotel in Washington D.C. — in the old Post Office Pavilion leased from the General Services Administration — was particularly notable: foreign governments and diplomatic delegations booked the hotel, and the GSA was both the landlord and a federal agency under presidential authority. Three lawsuits were filed against Trump under the Emoluments Clauses; all were ultimately dismissed without reaching the merits after Trump left office. Congressional oversight requests for information about foreign payments were resisted throughout.
Unlike every president in modern history, Trump refused to divest from his businesses, instead placing them in a trust managed by his sons. Foreign governments and domestic government agencies spent millions at Trump properties during his presidency. Courts dismissed emoluments cases on procedural grounds rather than merits; a House investigation documented over $750,000 in government spending at Trump properties through 2020.
The Office of Special Counsel — an independent federal watchdog — found that Trump administration officials committed the most extensive Hatch Act violations in the law's history. The 2020 Republican National Convention used the White House as a backdrop for campaign speeches by administration officials, naturalization ceremonies were used as political props, and senior White House staff used official accounts and positions to campaign. The administration declined to take any corrective action, with Conway reportedly saying she 'didn't care.'
The Southern District of New York opened an investigation into the inaugural committee in 2019 after the Cohen cooperation. Prosecutors subpoenaed records investigating potential coordination with foreign nationals and possible misuse of nonprofit funds. Tom Barrack, who chaired the fundraising effort, was indicted in July 2021 on charges of acting as an unregistered foreign agent of the UAE, obstruction of justice, and making false statements. The indictment alleged Barrack had used his position in the Trump campaign and inaugural committee to influence U.S. policy and public statements in favor of the UAE. Barrack was ultimately acquitted at trial. The investigation also found that donors linked to the UAE, Saudi Arabia, and Qatar may have funneled money through straw donors.
Pruitt's EPA tenure was defined by serial self-dealing: he flew first-class and chartered government planes citing 'security threats' that his own security detail denied, leased a Capitol Hill condo for $50/night from the wife of an energy lobbyist (when the EPA was processing that lobbyist's clients' cases), directed his security detail to run personal errands and sourced a used mattress from Trump International Hotel, and asked his scheduler to seek Chick-fil-A franchise opportunities for his wife. He resigned in July 2018 as 14 separate federal ethics investigations were underway.
Prior presidents had either sold their business assets or placed them in blind trusts managed by independent trustees. Trump placed his holdings in a revocable trust managed by his sons Donald Jr. and Eric, with Trump retaining the ability to revoke the trust at any time and receiving financial reports about the businesses. The Office of Government Ethics stated the arrangement was insufficient to prevent conflicts. The Trump International Hotel in Washington, housed in a federally-owned building under a lease Trump's own government administered, became a center of lobbying activity, with foreign governments and domestic interest groups booking events and rooms to seek favorable treatment. Saudi Arabia spent more than $270,000 at the hotel in a single year.
The Trump Foundation, a charitable organization, was found by the New York AG to have engaged in a pattern of illegal conduct including: making a $25,000 donation to Florida AG Pam Bondi (who was deciding whether to open a Trump University investigation), purchasing a $20,000 portrait of Trump, paying off legal settlements for Trump businesses, and illegally coordinating with the Trump 2016 presidential campaign. Trump had also used foundation money to pay personal legal settlements — including $258,000 to resolve lawsuits involving his businesses.
Flynn was paid over $530,000 by a Turkish-controlled entity while serving as one of Trump's most prominent campaign surrogates in 2016 — work he initially did not disclose and later retroactively registered as foreign agent activity. He lied to FBI investigators about his December 2016 contacts with Russian Ambassador Kislyak, in which he discussed sanctions that the Obama administration had just imposed on Russia for election interference. Flynn pleaded guilty to making false statements in December 2017, cooperated with Mueller, then attempted to withdraw his plea, and was ultimately pardoned by Trump in November 2020.
The $130,000 payment to Daniels was made by Cohen 11 days before the 2016 election to prevent her account from influencing voters. Trump reimbursed Cohen through Trump Organization checks falsely described as payments for legal services. The Manhattan DA's office prosecuted Trump for the falsification of business records; a jury of 12 New Yorkers convicted Trump on all 34 counts on May 30, 2024. Trump was the first sitting or former U.S. president convicted of criminal offenses.
The prosecution established that Trump directed Michael Cohen to pay Stormy Daniels $130,000 eleven days before the 2016 election. Trump reimbursed Cohen through a series of false invoices and checks falsely recorded as 'legal expenses' — the 34 counts all arose from these falsified records. The Manhattan DA alleged the falsification was done to conceal the underlying crime of election fraud (influencing an election through unlawful means). The case also documented the AMI/National Enquirer arrangement in which the tabloid bought and suppressed stories from McDougal and others — the 'catch and kill' scheme. Trump was sentenced to an unconditional discharge on September 18, 2024, but the conviction remained on record.
The New York AG investigation found that the Trump Foundation was used as a checkbook for Trump's personal and business interests rather than charitable purposes: charitable funds settled legal disputes for Trump businesses, purchased a $10,000 portrait of Trump, made politically timed donations, and were illegally coordinated with the 2016 campaign. Trump was required to pay $2 million to legitimate charities as a penalty.
Cohen's guilty plea was not just his own conviction — it was Trump's implication. Cohen stated in federal court that the campaign finance crimes (the Daniels and McDougal payments) were committed 'in coordination with and at the direction of' a candidate for federal office. The federal prosecutors who accepted his plea treated Trump as an unindicted co-conspirator. Cohen served three years in federal prison; Trump, protected by the OLC no-indictment policy, was not indicted federally until after leaving office.
The Trump Tower Moscow project involved Cohen emailing Kremlin spokesman Dmitry Peskov's office in January 2016 seeking Putin's personal assistance advancing the project. Trump signed a letter of intent in October 2015. Negotiations continued through June 2016. Cohen testified to Congress in 2017 that negotiations ended in January 2016 — a lie he later admitted under oath. The project would have been the largest Trump deal ever, potentially worth hundreds of millions of dollars and requiring Russian government approval. Throughout this period, Trump repeatedly denied any Russian business dealings and publicly advocated for lifting sanctions on Russia.
The Bank Secrecy Act requires casinos to file Currency Transaction Reports (CTRs) for cash transactions over $10,000 and Suspicious Activity Reports (SARs) for transactions that appear to involve money laundering. FinCEN found that Trump Taj Mahal had willfully failed to file CTRs and SARs, allowed transactions structured to avoid reporting thresholds (known as structuring — itself a federal crime), and maintained an anti-money laundering program with known deficiencies for years without correction. The settlement required payment of $10 million and an admission that violations occurred. The casino had also received a previous warning from regulators in the 1990s about similar violations — meaning the failures were repeated over more than two decades.
FinCEN found that the Trump Taj Mahal had, over the course of years, failed to file Currency Transaction Reports (CTRs) on large cash transactions as required under the Bank Secrecy Act, failed to maintain adequate Suspicious Activity Report (SAR) programs, and failed to maintain basic anti-money-laundering controls. The violations were documented across thousands of transactions. FinCEN described the violations as 'willful' — meaning the casino knew what was required and did not comply. The $10 million fine was FinCEN's largest-ever against a casino; the previous Trump casinos had also faced regulatory action.
The National Enquirer's 'catch and kill' program operated by buying the rights to stories from people with negative accounts of Trump — paying them for exclusives and then killing the stories. AMI purchased stories involving alleged sexual affairs and other damaging material. Federal prosecutors concluded the scheme constituted illegal campaign contributions; AMI entered a non-prosecution agreement admitting this. David Pecker's cooperation was central to the conviction of Michael Cohen and the eventual conviction of Trump himself.
Trump SoHo buyers, including an investor group led by Sateesh Bhagat, discovered that marketing materials claiming 60% of units were sold were false — fewer than 15% had been sold. They sued for fraud. The Manhattan DA opened a parallel criminal investigation. In 2012, after Trump lawyers met with DA Vance, the investigation was dropped. Vance later received a $25,000 campaign contribution from Kasowitz's law firm, which he initially kept and later returned; Vance denied it influenced his decision. The Bhagat investor group settled civilly for $3.16 million. The pattern — criminal investigation followed by dropped charges after private meeting — resembled the Bondi situation in Florida.
Trump University promised to teach students Trump's real estate 'secrets' through courses taught by his handpicked instructors. In practice, it was found to be a high-pressure sales operation that extracted money from vulnerable people — including elderly retirees — through a series of escalating upsells. New York's attorney general sued for $40 million; a California class action settled for $25 million in 2016.
Trump University was not a real university — it had no degree programs, no accreditation, and was not approved to use the word 'university' in New York. Students paid from $1,495 for a preview seminar to $35,000 for a 'Trump Elite' mentorship package. Former employees provided sworn declarations that they were instructed to aggressively upsell students to higher-priced programs and use high-pressure sales tactics. Student evaluation forms praised instructors at the time — but these were collected before students could assess outcomes. Former Trump University president Michael Sexton acknowledged the program was selling a brand, not education. Trump had selected none of the instructors himself, contradicting his marketing claims.
Trump University was not an accredited university and did not grant degrees. It marketed heavily using Trump's image and promises that students would learn from Trump's 'handpicked instructors.' Playbooks obtained by Washington Post showed instructors were coached to identify students' financial resources and upsell them to higher tiers; students were encouraged to raise credit card limits to pay for more expensive packages. Former employees testified to high-pressure sales tactics. The $25 million settlement resolved claims by approximately 6,000 students and was approved by a federal judge in April 2017.
Trump's Atlantic City casinos were overleveraged from the beginning: the Taj Mahal alone carried $675 million in junk bonds at 14% interest when it opened in 1990. When revenue fell short of the debt service requirements, bankruptcy followed. Through six rounds of bankruptcy, Trump negotiated deals that preserved his equity stake or management role while bondholders received cents on the dollar. He personally profited $82 million in salary and fees from the casinos between 1995 and 2009 while publicly traded Trump Hotels & Casino Resorts lost $1.4 billion. Trump repeatedly characterized the bankruptcies as strategic use of 'the laws of this country' and claimed he had made 'a lot of money' on Atlantic City.
Trump's Atlantic City ventures were financed substantially through junk bonds. The Trump Taj Mahal opened in April 1990 carrying $675 million in junk bond debt at interest rates of 14 percent; by December 1990 it was behind on interest payments. The first bankruptcy followed in 1991. Trump subsequently filed bankruptcies involving his casino holdings in 1992, 2004, and 2009. In each restructuring, bondholders and creditors took substantial haircuts. Trump negotiated to retain management fees and significant equity stakes as conditions of restructuring. He ultimately sold his remaining stake in Trump Entertainment Resorts in 2009 and 2010. Trump characterized the repeated bankruptcies as smart use of the legal system; critics noted the losses were borne primarily by investors and creditors, not Trump personally.
Trump's Atlantic City casinos — the Taj Mahal, Plaza, Castle, and related entities — were financed with junk bonds carrying interest rates of 14-17%, which were unsustainable given the revenue the casinos could generate. Trump had collected hundreds of millions in management fees, licensing fees, and development profits before the bankruptcies. When the companies collapsed, thousands of bondholders, including retirees who had purchased the high-yield bonds, received pennies on the dollar or nothing.
The Times investigation identified multiple strategies: Fred Trump created a shell company called All County Building Supply & Maintenance to collect money from Trump properties, which was then used to justify large increases in maintenance fees that were passed to Trump children as untaxed income; Fred Trump's estate was valued at far below market rates to reduce estate taxes; and the children, acting in concert, were able to receive hundreds of millions in what amounted to gifts but were legally classified in ways that minimized tax exposure. The New York Department of Taxation opened a review.
Trump's NDA culture predated the presidency. Former Trump Organization employees described comprehensive NDAs covering all aspects of their employment. The campaign NDAs were drafted by Trump's attorneys and covered staffers, volunteers, and contractors. Several current and former employees who spoke to journalists anonymously or were approached by journalists described fear of legal action as the primary reason they declined to speak on the record. Michael Cohen's 'catch and kill' operation with AMI (American Media Inc.) extended the silencing mechanism to women who alleged sexual misconduct. Omarosa Manigault Newman, a former White House employee, claimed she was pressured to sign an NDA after her departure that would have prohibited any public criticism of Trump.
The Times obtained decades of Fred Trump's tax records showing the family used fraudulent asset undervaluation, sham consulting fees, and a dummy corporation ('All County Building Supply') to transfer over $1 billion in wealth to Trump and his siblings while evading hundreds of millions in estate and gift taxes. A separate 2020 investigation found Trump had paid virtually no federal income tax for years.
Trump purchased the Eastern Air Shuttle for $365 million in 1988 and renamed it Trump Shuttle. Unable to make debt service payments on the junk bonds used to finance the purchase, Trump lost control of the airline to creditors in 1992 — it operated for only four years. Trump Steaks were sold through The Sharper Image beginning in 2007 and discontinued within two months due to poor sales. Trump Magazine was launched in 2007 and folded within five months. Trump Vodka was launched in 2005 and discontinued by 2011. The pattern across these ventures was consistent: launch with celebrity promotion, heavy licensing of the Trump name, and eventual failure attributed to market conditions.
Tony Schwartz spent 18 months with Trump to research and write The Art of the Deal. By his account, Trump's attention span was limited, he rarely focused on any topic for more than a few minutes, and most of what appeared in the book was invented or shaped by Schwartz from fragments of Trump's statements. The book created the public image of Trump as a brilliant real estate dealmaker — an image Trump leveraged throughout his political career as evidence of his fitness for office. Schwartz's 2016 interviews in The New Yorker and subsequent public statements described the book as a fabrication of Trump's public identity and said he feared Trump becoming president.
The New York AG's investigation found: Trump used foundation funds to settle legal obligations of his businesses (including a $100,000 payment from the foundation to settle a lawsuit against Mar-a-Lago), purchased items for personal use (including a $10,000 portrait of himself and a $12,000 signed Tim Tebow helmet), directed foundation funds to charities at political events in exchange for applause in possible violation of campaign finance law, and improperly used the foundation to pay a $25,000 contribution to a political organization supporting Florida Attorney General Pam Bondi — who subsequently declined to investigate Trump University fraud claims. Trump did not have meaningful control over the foundation, which was run largely by his children without proper board oversight.
USA Today and other outlets documented a decades-long pattern in which Trump companies refused to pay contractors, vendors, and workers after completion of their work. Affected businesses included a dishware supplier, a plumbing contractor, a piano bar operator, and hundreds of others. Trump's negotiating strategy, described by associates, was to refuse payment and force small businesses to accept pennies on the dollar rather than face litigation.
The 2019 NYT investigation used IRS data from 1985-1994, finding Trump declared $1.17 billion in losses — an average of $117 million per year — largely from casino and real estate failures. The losses were so large that Trump paid no income tax in eight of the ten years. The 2020 investigation of complete tax returns found Trump paid $750 in federal income taxes in 2016 and $750 in 2017 through aggressive deductions, carried-forward losses, and tax credits. Trump had for decades refused to release his tax returns, claiming he was under IRS audit. He remained the only presidential candidate in modern history to refuse release until his returns were eventually obtained by courts after litigation.
The USA Today investigation identified at least 200 contractors, companies, and individuals who claimed Trump failed to pay them for their work. Victims included small businesses that were left near bankruptcy by the nonpayments. A Venetian glass supplier from the Trump Tower lobby renovation said Trump reduced his payment by $350,000 and told him to sue; the supplier could not afford protracted litigation. Dishwashers and waiters at Trump's Atlantic City casinos described being denied wages and having to sue to recover even small amounts. Trump's lawyers routinely challenged the quality of work performed, even for long-completed projects, and offered settlements far below what was owed.
Building in 1980s New York required navigating a concrete industry dominated by organized crime. Trump Tower, built 1980-1983, used S&A Concrete, a company co-owned by Anthony 'Fat Tony' Salerno (Genovese crime boss) and Paul Castellano (Gambino crime boss) through intermediaries. Trump's relationship with Roy Cohn — who simultaneously represented multiple mob clients — connected him to the broader organized crime ecosystem. His Atlantic City casinos dealt with labor unions whose pension funds and leadership had documented mob ties. These relationships did not make Trump a mobster; they documented the environment in which he built his early business empire and the tolerance or accommodation he showed to organized crime-connected business partners.
USA Today's 2016 investigation found that Trump and his companies had been sued more than 3,500 times in U.S. federal and state courts over the previous three decades, with a significant portion related to nonpayment claims by contractors, vendors, and employees. Among those who reported not being paid: drapery installers, piano players, porters, waiters, dishwashers, real estate brokers, plumbers, and hundreds of hourly workers. Trump's standard response was to challenge the quality of work — often leaving small contractors to choose between expensive litigation or accepting partial payment.
Trump met Roy Cohn at Studio 54 in 1973 during the housing discrimination lawsuit. Cohn became his attorney, fixer, and strategic advisor for over a decade. Cohn represented Trump in multiple legal matters and taught him a specific political and legal style: never settle (except when you do), never apologize, and reframe every defense as an attack. Cohn's other clients during this period included mob boss Fat Tony Salerno, Gambino crime family figures, and New York tabloid figures. Trump's Atlantic City casino construction involved documented relationships with contractors controlled by the Genovese crime family; the concrete supplier for Trump Tower and other Trump projects was S&A Concrete, co-owned by Salerno and Paul Castellano.
Roy Cohn served as Donald Trump's attorney and mentor from the early 1970s until Cohn's death in 1986. Cohn — who had been Joseph McCarthy's chief counsel during the Red Scare, was later disbarred, and died of AIDS while denying he had it — introduced Trump to organized crime figures connected to the Genovese and Gambino families, taught him to use litigation as a weapon rather than a legitimate process, and instilled the maxim 'never apologize, never admit.' Trump's operating philosophy throughout his career directly reflects Cohn's explicit teachings.
The four student deferments were legal and widely used by college students of the era. The 1968 bone spurs medical deferment, obtained after Trump's student deferments expired at graduation, came from Dr. Larry Braunstein, a podiatrist in Jamaica, Queens — a building owner named Fred Trump. Braunstein's daughters told the New York Times in 2018 that their father provided the diagnosis as a 'favor' to Fred Trump, the landlord. Trump has described his bone spurs in varying ways over the years, at times saying they had healed on their own and at other times appearing not to remember which foot was affected. He has praised military service at Veterans events while criticizing specific veterans including John McCain for being captured.