What specific transactions did the Trump Foundation make that regulators flagged as improper?

1. The legal finding: “shocking pattern of illegality” and the remedy

New York Attorney General Barbara Underwood sued the Trump Foundation alleging a “shocking pattern of illegality,” and a court-ordered settlement in 2019 required the foundation to dissolve under supervision and Trump to pay $2 million to eight charities as restitution ^{[1] [2]}. The attorney general’s office listed admissions and specific restrictions on future charitable activity as part of the resolution ^[2].

2. Veterans fundraiser in Iowa: campaign coordination, not charity

Regulators flagged a veterans fundraiser held during the 2016 Iowa campaign as improperly run: Donald Trump admitted the event was coordinated with his presidential campaign and that funds raised were turned over to the campaign rather than used solely for charitable purposes, a use that violated nonprofit rules ^{[3] [1]}. The attorney general’s office and later the settlement treated that fundraiser as political activity masquerading as charity ^[2].

3. Payments that benefitted Trump businesses: self‑dealing admissions

Investigators found instances of self‑dealing — transfers of foundation assets that benefited Trump or Trump-owned businesses — and the foundation itself admitted to having transferred “income or assets to disqualified persons” on its IRS filings during the probe ^[1]. The settlement required reimbursements and restrictions because tax-exempt charities may not be used to line the pockets of their founders or related businesses ^{[1] [2]}.

4. Hole‑in‑one prize settlement at a Trump course — $158,000

The foundation paid $158,000 to resolve a lawsuit over a hole‑in‑one prize at a golf tournament held at a Trump-owned course; regulators flagged that payment as an improper use of charitable funds because it directly benefited a Trump business interest ^[3]. That transaction was singled out in coverage of the judge’s findings and Trump later acknowledged it as improper ^[3].

5. Promotional ads for Trump hotels — $5,000

Regulators identified a $5,000 payment by the foundation that bought advertising space promoting Trump hotels in charity-event programs; the payment was cited as an impermissible benefit to Trump businesses and was admitted by Trump to be improper ^[3]. The attorney general’s follow-up materials list this among transactions that crossed the line from charitable grantmaking into commercial promotion ^[2].

6. Reimbursements for gala purchases and other miscellaneous improper charges

As part of the resolution, Trump was ordered to reimburse the foundation for items such as sports memorabilia and champagne purchased at a charity gala — amounts the attorney general quantified and added to the foundation’s account reconciliations (notably $11,525 mentioned in the attorney general’s release) — indicating regulators viewed certain personal or event expenses as improperly charged to the charity ^[2].

7. What sources say about scope and admissions — and what they don’t

The official New York Attorney General release and contemporaneous reporting specify the above transactions and describe broader admissions — including Trump’s acknowledgement that the foundation was used for political and business purposes — and the requirement to pay $2 million to a slate of charities ^{[2] [1]}. Available sources do not mention other specific individual transactions beyond those cited here; they do note broader categories of self‑dealing admitted on IRS filings but the filings “did not provide specifics” on every past transfer ^[1].

8. Competing viewpoints and context

Mainstream coverage and the attorney general framed these transactions as clear violations warranting dissolution and restitution ^{[2] [1]}. Trump’s public statements framed the penalties as politically motivated, emphasizing his charitable giving history; however, the court ruling and settlement recorded Trump’s admissions about improper uses ^{[3] [1]}. Independent commentary since then has connected this episode to broader concerns about mixing political, business, and charitable activity ^[4].

9. Bottom line for readers

Regulatory findings and the court settlement list concrete examples — the Iowa veterans fundraising coordination, payments benefiting Trump businesses (including a $158,000 golf‑prize settlement and $5,000 in hotel ads), and reimbursements for gala purchases — as improper transactions that led to the foundation’s ordered dissolution and a $2 million penalty ^{[3] [2] [1]}. For additional specifics beyond what these sources document, available sources do not mention them.