A few months ago, I wrote about one of my favorite phrases used by Democratic politicians in Washington, D.C.: “Pay your fair share.” Politicians love saying wealthy Americans aren’t paying enough. The problem is the numbers tell a different story.
The top 1% of taxpayers already pay roughly 40% of federal individual income taxes. The top 10% pay the overwhelming majority of taxes. So, here’s my question.
If that isn’t enough, what exactly is enough?
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Because the debate isn’t stopping at ordinary income taxes. Soon it will be capital gains taxes, Social Security taxes and then estate taxes. Here are five more ways successful Americans could increasingly find themselves paying even more.
This is the easiest one. Need more money? Raise the top tax bracket.
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But high earners already pay the highest federal marginal income-tax rate, plus state income taxes that can push combined marginal rates significantly higher in places like California and New York.
At what percentage does “fair share” officially become fair? The last time the top tax rate was above 39.6% was 40 years ago, when it was 50%. Could it be 50% again? No political candidate will tell you that number.
Here’s another Washington favorite. This one is sneaky and likely the No. 1 tax angle to be attacked if political winds change in the White House. Tax investment gains more like ordinary income.
Sounds simple until you remember where investment capital comes from. People risk money starting companies, funding businesses, buying stocks and investing in real estate because they hope to earn a return.
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You can tax that return more heavily. Just don’t pretend people won’t change their behavior when you do that, because they will.
Why wait until somebody earns money? Some politicians want to tax wealth simply because someone owns it. That’s a completely different ballgame.
Imagine building a company worth $100 million but not having $100 million sitting in your checking account. Your business might be worth a fortune on paper while your actual cash is tied up inside the company.
Now Uncle Sam wants a piece before you even sell it. California will tell us the first chapter of this story on the November ballot.
America already has a federal estate tax. For 2026, estates above the federal exemption can face a top estate-tax rate of 40%. Some states can take another bite.
Think about that. You earn the money. You pay income taxes. You invest what’s left.
And when you die, the government may want another piece of what’s still sitting there. There’s a $15-million exemption today, but what if this reverts to 2000 levels, when the number was less than $1 million? Imagine your kids, your heirs and your family having to pay 50% or more to the government when you die?
How many times does the same dollar need to be taxed before everybody agrees it finally paid its fair share?
This may be the sneakiest one. Don’t raise the headline tax rate. Just add another little tax. There’s already the 3.8% Net Investment Income Tax and the additional 0.9% Medicare tax on certain higher earners.
States are getting into the game as well. Massachusetts has its millionaire surtax. California has its own high-income surtax. One percent here. Four percent there. Eventually, all those “little” taxes start looking pretty big.
Congress wrote the loopholes.
If Congress doesn’t like a provision in the tax code, change it. But don’t vilify taxpayers for following the rules Congress created. That’s the bigger issue with America’s “fair share” debate.
Maybe some taxes should go up. Maybe some deductions should disappear. Maybe certain strategies should be eliminated. We can have that debate.
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But first, politicians should answer one incredibly simple question: What exactly is fair?
Because until somebody puts an actual number on it, “fair share” isn’t tax policy. It’s just two words politicians use when they want more of somebody else’s money.
