Trump Foundation Pays $258,000 for Six-Foot Portrait of Trump at Charity Auction

The Donald J. Trump Foundation paid $258,000 in charitable funds to purchase a six-foot portrait of Donald Trump at a charity auction in Palm Beach, Florida. The portrait, painted by artist William Quigley, was supposed to be sold to benefit charity, but instead the Foundation used tax-exempt charitable donations to acquire an item of purely personal benefit to Trump. The massive portrait was later discovered hanging at Trump’s Doral golf resort in Miami, confirming it provided no charitable purpose and instead decorated Trump’s for-profit business property.

Background

The purchase occurred at a charitable auction in the Hamptons, where wealthy attendees bid on artwork and experiences with proceeds ostensibly benefiting charitable causes. The Trump Foundation, which was required by law to use all funds exclusively for charitable purposes, had increasingly been used by Trump as a personal checkbook rather than a legitimate charitable organization. The Foundation had not received any contributions from Donald Trump personally since 2008, instead operating entirely on donations from others that Trump directed to various causes - and increasingly, to himself.

The six-foot portrait represented the single largest documented self-dealing purchase by the Trump Foundation, though Washington Post investigative reporter David Fahrenthold would later uncover multiple similar violations. Federal tax law strictly prohibits 501(c)(3) charitable foundations from using charitable assets to benefit their founders or directors. Using foundation money to purchase a portrait of yourself, which then decorates your own business property, represents textbook self-dealing and violation of the foundation’s tax-exempt status.

Significance

This egregious example of self-dealing became a centerpiece of the New York Attorney General’s 2018 lawsuit against the Trump Foundation, which characterized the organization as having “operated in persistent violation of state and federal law” for over a decade. The lawsuit cited the $258,000 portrait purchase as evidence of a systematic pattern of Trump using charitable funds for personal expenses, business settlements, and campaign activities.

The incident demonstrates Trump’s long-standing pattern of treating charitable organizations as personal slush funds, mixing charitable assets with business and personal interests with no regard for legal or ethical boundaries. In 2019, a New York judge ordered Trump to pay $2 million in damages to legitimate charities and mandated that Trump and his children complete mandatory training on the proper operation of charitable organizations, with the court finding 19 admitted violations including the portrait purchase. The Trump Foundation was dissolved under court supervision, with its remaining assets distributed to actual charities rather than continuing to fund Trump’s vanity and business interests.