Trump Said the System Was Rigged. Now He Sits at the Top of It.

Deconstructing the Mule

By Yiannis Damellos and Mars Strangelove Jr. on Duty

October 24, 2026

“The system is rigged.” Donald Trump spent the 2016 campaign telling Americans that the powerful manipulated the rules, escaped accountability, and used their connections to protect their fortunes. He promised to change that system and "drain the swamp". A decade later, a Forbes investigation raises a question with extraordinary implications: what happens when the president seeking protection from tax scrutiny is also the man sitting at the top of the government responsible for enforcing the tax laws?

Forbes reporter Dan Alexander explains how Trump could turn charitable deductions on golf courses he still owns into hundreds of millions of dollars in tax savings — while using a lawsuit against the IRS to secure protection from scrutiny.

Donald Trump could save an estimated $450 million in taxes through a series of charitable deductions tied to his golf properties. But the most consequential part of the story, according to Forbes senior editor Dan Alexander, is not simply the size of the tax break. It is the president’s attempt to protect himself from the government agency responsible for examining whether those deductions are legitimate.

Speaking to CNN’s Erin Burnett on October 19, Alexander explained that Trump sued the Internal Revenue Service in January in his personal capacity while simultaneously serving as president, with authority over the executive branch overseeing the agency. Alexander said the resulting settlement barred the government from pursuing certain past claims against the Trump Organization. The arrangement, he argued, potentially removed a major obstacle to Trump’s aggressive tax strategy. A federal judge subsequently ruled the agreement unlawful and voided it, although Trump is appealing.

The underlying tax maneuver involves conservation easements. Property owners can receive charitable deductions for surrendering development rights to protect land, even while retaining ownership of the property. Trump’s golf courses, however, remain operating businesses. According to Alexander, the crucial financial calculation comes from valuing the land as if it could be divided into expensive residential lots, rather than valuing it as a golf course. The difference can produce enormous deductions on paper.

“Golf courses aren't worth all that much money because they don't turn out huge profits,” Alexander explained. But if an appraiser calculates what the land might fetch if divided into housing lots, the resulting valuation can be dramatically higher. The difference between the two values, he said, creates an opportunity to claim deductions that could potentially return the original investment and more through tax savings.

The Jupiter, Florida, property illustrates the scale. Forbes estimates the club is worth approximately $120 million, yet the donated development rights could generate a deduction of up to $825 million. That is a potential deduction, not $825 million in tax savings. Across five conservation-easement transactions dating back to 2005, Forbes estimates Trump could shelter more than $1 billion in income and save approximately $450 million in taxes. The IRS has challenged conservation-easement arrangements in the past, and the legitimacy and valuation of individual deductions remain matters for scrutiny.

Alexander also identified a striking potential conflict of interest. Frank Bisignano, the IRS chief executive, owns a home backing onto Trump’s Jupiter golf course, the very property involved in the latest conservation-easement deal. Alexander described him as one of the easement’s beneficiaries. Attorney General Todd Blanche, meanwhile, signed off on the settlement that sought to restrict government claims against Trump and his business.

The question raised by Alexander’s reporting is therefore bigger than a wealthy property owner claiming a disputed deduction. It concerns whether a president can use his position to secure protection from tax scrutiny while officials in his own administration control the institutions responsible for enforcing the law. The settlement has been voided by a federal judge, and its final legal status remains subject to appeal. But the financial stakes — and the potential conflict between private interests and public office — are already substantial.

Source: CNN’s interview with Dan Alexander on Erin Burnett OutFront, October 19, 2026. See also Alexander’s Forbes investigation.