The No-Work Way to Wealth — When Losing is Winning

Bren Kelly
5 min readDec 23, 2022

Trump Tax Returns Shows the Biggest Loser

The Scales of the Tax Auditor for the Super Rich
The Scales of the Tax Auditor for the Super Rich are Balanced — she can just feel it [Photo by Tingey Injury Law Firm on Unsplash]

When Trump told his fan base during the first election cycle “You’re going to get so sick of winning”, he meant by playing the other popular reality TV show Biggest Loser. He must have been. Despite all the tax tricks the uber-rich pull off, the idea net losses mastered by Trump prove he’s in that special category of American Winners: the Biggest Loser.

The initial recap from his released tax forms — from which there will be plenty of excuses and backpedaling and taxsplaining on how being rich works to folks like me in middle America is yet to come — is that he lost. Like a lot. While the rest of America was busy trying to stay afloat to earn money, Trump was trying to drown.

The numbers indicated that from 2015–2020, he racked up $82 million in LOSSES and in 2018 and 19 his adjusted gross income was $29 million. He ended up paying $1.8 million in federal between those years of 15–20 will be declaring $53 million in losses. Yes, he owns real estate and has management deals he “earns” from, I get it. No matter the interpretation and “ultimate” buried tax deductions and investment portfolio in worth and whatever we have yet to see, the devil sometimes lies in the open, the obvious, instead of in the details: “I declare I lost $53 million” is one he signed off on.

In 2020, the last full year of his Presidency, he made $393 thousand from his full-time job of being president, and “earned” taxable interest of $10.6 million. But his real estate losses and “other losses” (for hair care maybe) give him a total income of NEGATIVE -$4.96 million.

While I’m no tax expert, it looks like there’s a bunch of problems here, just from being rich, not just from being a fake billionaire racking up losses. His taxable income is listed as $0 in 2020. He “earned” nothing worth taxing on. I’m betting among the super-rich and the regular very very rich, this is probably the norm. Nothing to see or to tax here, sorry, move on people, just a big nothing taxburger.

Compared to “working Americans,” like the 99% of them, we do have actual “earned” income to tax. In other words, we are adding value to society by working on the clock. They get money by having other people move theirs around the clock…



Bren Kelly

Engaged in new Ideas and old Inequalities, dismantling the system in systemic, born on the 50th Anniversary of Women's Lib Day, still seeking injustices.