President Donald Trump appears to believe that money earned through proximity to him comes with a price. Anyone who profits from his political orbit may eventually discover that the boss expects a cut, preferably directed toward his presidential library or another Trump related entity.

The spectacle makes comparisons between the White House and an organized crime operation feel uncomfortably apt. Since returning to office last year, Trump has become immensely wealthier while bristling when people around him profit without offering what he apparently considers proper tribute.

Alina Habba Mildon, Trump’s former personal lawyer and a former U.S. attorney for New Jersey, is the latest person to attract his irritation. Mildon reportedly signed a $50 million contract last year to serve as general counsel for a billionaire Venezuelan family.

The New York Times reported Thursday that Trump “has told aides and allies that she should donate a portion of that money to his future presidential library or another Trump-related entity, according to multiple people briefed on the conversations.” It is quite the arrangement when professional success near the president starts looking like a bill awaiting payment.

Trump’s resentment toward associates who make money from his political brand is hardly new. Brad Parscale, his digital strategist in 2016 and campaign manager in 2020, collected millions through contracts between his strategy company and groups affiliated with Trump.

“That’s my money!” Trump reportedly exclaimed after learning about Parscale’s expensive lifestyle. Parscale was demoted in July 2020 and stepped down entirely before Election Day, providing a memorable example of what can happen when the money flows without satisfying Trump.

Earlier this month, 2024 joint campaign manager Chris LaCivita and adviser James Blair faced criticism over political work in Republika Srpska. The Balkan territory’s nationalist government is aligned with Russia, and the two men reportedly earned hundreds of thousands of dollars each while their attention was diverted from the U.S. midterms.

Chief of Staff Susie Wiles’ daughter also performed contract work for the Serbian enclave inside Bosnia and Herzegovina. Wiles’ enemies have reportedly reminded Trump about that work while attempting to win his favor.

Trump threatened to cut LaCivita and Blair off, but they regained his approval through what he called “charity.” Both donated the money they earned from consulting in Republika Srpska to the Trump presidential library and celebrated the decision in glowing social media posts.

The Times said “it is not known whether [Trump] explicitly asked [Mildon] to make a donation or only suggested it to others.” Still, the episode follows a model in which associates can apparently repair their standing by sending money toward a project bearing Trump’s name.

That marks a shift in how money has traditionally moved through Trump’s orbit. Would be influence buyers have purchased Mar-a-Lago memberships, scheduled meetings at Trump properties and spent heavily while seeking possible access, while questionable cryptocurrency deals have supplied much of Trump’s earnings this term.

Trump has repeatedly offered buyers of his otherwise useless currency a chance to win dinner with him. He has also used private donations to federal projects as another route for wealthy people and companies seeking to get on his good side.

The Washington Post reported earlier this month on donors behind $330 million raised for Trump’s White House ballroom project. Although the newspaper did not establish a link between donations and favorable administration actions, it found that most of the money came from wealthy individuals and companies with interests before the federal government.

Money directed toward Trump’s presidential library does not make the arrangement less disturbing. The initial library fund was dissolved last year without satisfactory answers about millions in pledged contributions, while a second nonprofit established in December said it had collected $50 million, below the approximately $63 million previously pledged.

Several million dollars came from media outlets and social media companies that agreed to contribute while settling lawsuits Trump brought personally. Now the apparent reward for writing a check may simply be removal from Trump’s potential enemies list, a fitting transaction for a president who treats another person’s gain as his own loss.

For Trump, his personal brand remains the prized commodity, and anyone benefiting from it risks being viewed as withholding his rightful share. The danger is that a sitting president has the power of his office available when deciding how aggressively to collect what he believes he is owed.