What's the Matter with Billionaires?

How America's wealthiest sabotage their own prosperity (and ours) to avoid paying taxes

As markets reel from the latest Trump-induced crisis—escalating tariff threats sending shockwaves through global supply chains and stock prices—it’s worth asking: Why do America's wealthiest individuals continue to support politicians who appear to work against their economic interests?

None of this should come as a surprise to GOP-supporting billionaires. Trump is doing exactly what he promised during his campaign—sowing chaos and imposing tariffs. He ran explicitly on economic nationalism and trade wars. This isn't a one-off crisis or an unexpected policy shift; it's the predictable implementation of his stated agenda. The billionaires who bankrolled his campaign knew—or should have known—precisely what they were buying. Yet they still chose to support policies that have historically hindered their own wealth accumulation.

I analyzed over 40 years of Forbes 400 data and found a striking pattern: billionaire wealth grows significantly faster under Democratic administrations (+57.1% average growth) compared to Republican ones (+16.5%).

This isn't just a minor difference—it's substantial. During the Clinton years, we saw a staggering +128.7% growth in Forbes 400 wealth over a four year period. The Obama administration delivered solid growth across both terms, reversing the losses from the 2008 financial crisis. And despite various economic challenges, the Biden administration generated +64.6% growth for billionaires.

The explanation is straightforward. Billionaire fortunes rise and fall with markets, not salaries. The ultra-wealthy build wealth primarily through asset appreciation—stocks, real estate, intellectual property—rather than traditional income. When markets thrive, as they historically have under Democratic administrations, billionaire wealth multiplies accordingly.

If Democratic administrations have been so beneficial for wealth creation, why did so many billionaires support Trump and the GOP in 2024, including several high profile defections in Silicon Valley? Why do they continue to support a party that has consistently delivered worse results for their bottom lines?

It’s the Taxes—Or Lack Thereof…

The billionaire revolt against Harris's endorsement of a proposed 25% minimum tax on unrealized gains for fortunes exceeding $100 million perfectly illustrates how this single issue overrides all other political considerations for the ultra-wealthy. Marc Andreessen warned the proposal would "kill startups and venture capital" and even "kill the California tax base," calling it "insane" and something that would "single-handedly crush the economy." Elon Musk similarly railed against it, tweeting, "Eventually, they run out of other people's money and then they come for you."

Even billionaires who supported Harris opposed this tax. Mark Cuban, while campaigning for Harris in Arizona, broke ranks on this issue: "When I saw that, I went ballistic because that's an economy killer," Cuban told a town hall audience, adding dramatically that if Harris implemented such a tax, "I'll work so she doesn't get elected again."

This visceral reaction wasn't about economic principles or market efficiency—it was naked self-interest. Billionaires have built elaborate financial structures that allow them to accumulate vast wealth while paying virtually no taxes. They borrow against their assets, deduct the interest payments, and live lavishly without ever realizing taxable income. Upon death, a special provision called the stepped-up basis wipes out all the taxes they would have owed, letting their heirs inherit wealth nearly tax-free, perpetuating dynastic fortunes.

The prospect of paying taxes on paper gains—something ordinary Americans do annually with their homes through property taxes—is where the bipartisan camaraderie among billionaires crystallizes. Their message is identical: don't touch our unrealized gains, or else.​​​​​​​​​​​​​​​​

A Dangerous Decoupling

What's most alarming about this trend is how it reveals the complete decoupling of billionaire interests from general economic prosperity. The ultra-wealthy appear willing to sacrifice overall economic health, market stability, and general prosperity to protect their privileged position. This isn’t rational economic behavior in the traditional sense—it’s a calculated decision by a rising oligarchic class that prioritizes tax avoidance and wealth preservation above all else. Rather than backing policies that create conditions for expanding the economic pie (which historically benefits them disproportionately), many have opted for policies focused on protecting their existing slice, even if it means the overall pie grows more slowly.

Trump exemplifies this dynamic perfectly. His plan to fund the government through tariffs is patently ludicrous and contradicts fundamental economic principles. No industry titan with a modicum of business acumen advocates for broad tariffs because they understand how devastating they are for commerce, supply chains, and economic stability. Yet billionaire support for Trump persists for one simple reason: he promised not to disrupt their tax avoidance schemes, while Democrats proposed making them pay closer to their fair share. For the ultra-wealthy, protecting their tax privileges apparently outweighs all other economic considerations—even if it means endorsing policies that harm their businesses and investments.

The ramifications of this are substantial. What we're witnessing isn't simply wealth concentration but the transformation of economic power into political power. Republicans are now largely dependent on the ultra-wealthy for fundraising. In 2024, a staggering 56% of total contributions to Republicans came from mega-donors giving over $1 million. This codependence is now driving America’s descent into oligarchy.

The Price of Plutocracy

The most damning reality: billionaires who've reaped unprecedented wealth from our economic system are actively undermining it to avoid contributing their fair share. This isn't just about tax fairness—it's about the viability of democracy itself when wealth translates so directly into political power.

While markets demonstrate that Democratic policies yield better returns even for the wealthy, the ultra-rich have decided that protecting their tax privileges is more important than actual wealth creation. Their hysteria about Harris's proposal to tax unrealized gains on fortunes over $100M—which would have affected only a tiny sliver of households—revealed their true concern: maintaining a separate set of rules. Their fear of Democrats isn't about economic collapse; it's being forced to participate in the same social contract as ordinary citizens.

As tariffs take their toll, remember that this economic damage is self-inflicted—the price of allowing an emerging oligarchy to protect its interests at the expense of shared prosperity. The billionaire paradox has become America's tragedy: a small elite willing to sacrifice both democratic principles and economic growth on the altar of their tax privileges. Perhaps the ultimate irony is that in their desperate bid to avoid paying their fair share, billionaires are dismantling the very economic and democratic systems that enabled their success in the first place.