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There is no such thing as a tax loophole, but here they are anyway

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AUTHOR: R Quinn on 5/17/2026

My opinion is that there is no such thing as a tax loophole. Plus it has a negative connotation I don’t think is accurate. In addition, there is a tendency to apply the word to others – mostly the wealthy, but not ourselves

Look up the word and you likely see something like “ A tax loophole is a provision, ambiguity, or gap in tax law that allows a person or business to legally reduce the amount of taxes they owe — often in ways lawmakers may not have originally intended.”

Long term gains are taxed at lower rates to make investing attractive. Municipal bond interest is tax-free to allow municipalities to raise funds at lower interest rates.  This goes back to 1913.They are not loopholes.

Are Roth accounts loopholes? How about Roth conversions? Nope, but perhaps excluding Roth withdrawals from MAGI, especially related to IRMAA premiums may be considered as such. Ask yourself this. Who can better afford higher premiums, the person withdrawing $75,000 from a taxable IRA or the one taking $75,000 from a Roth tax-free.  Seems like the logic is backward. If a person lives on $75,000 in municipal bond interest, is that not the same income level as Roth income?

Are QCDs a loophole, they certainly apply mostly to higher income Americans? They are a clear tax advantage that also helps society. 

Why is it a loophole if stock compensation is favored over salary? Stock compensation contains risk and sooner or later it will be taxed. Not unlike a 401k taxed as ordinary income decades after a contribution is made, when the earnings portion is actually capital gains. 

Receive non-qualified stock options and they are not taxed until exercised and value is achieved, then it’s ordinary taxable income and if the exercise is taken in stock shares, the gain above exercise price is taxed again as a capital gain. That’s what I did twenty years ago and still hold the shares. When my family inherits them, the basis will be reset and eventually they will pay capital gains –  intentional part of the IRC which benefits many average Americans with modest estates even while benefiting the super wealthy.  No actual gain is realized until a sale is made. 

Around 60% of CEO compensation is equity, not cash. Generally, when this compensation vests, it is taxed as ordinary income. For example, when restricted stock units (RSUs), vest they are taxed as ordinary income first, then capital gains or losses on later sale. This is sometimes called a loophole, but why? Stock compensation is intended as an incentive and the value is at risk. 

Is the mortgage interest deduction a loophole given it favors homeowners over renters? 

I don’t see any of this as loopholes. Every taxpayer seeks to minimize their taxes, hopefully legally and the tax code applies to everyone. The fact more money is involved for the super rich, doesn’t change that in my opinion. 

There are currently sixteen tax credits in place, all but one directly benefiting individual Americans. Are they loopholes if many of us are not eligible? 

So, keep trying to legally minimize your income taxes and avoiding IRMAA and take advantage of every “loophole.” 

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Michael Flack
1 hour ago

I think you make a valid argument that most tax loopholes come with a (potential) downside. Therefore I’m more concerned about antiloopholes such as the Foreign Tax Credit, IRMAA and that only $3,000 of tax losses can be carried forward.

Michael1
1 hour ago
Reply to  Michael Flack

I think you meant only 3k can be applied to ordinary income. There’s no such limit on how much can be carried forward.

Michael Flack
45 minutes ago
Reply to  Michael1

Michael2, Good point, though what I really mean is that after an investor sells his 1000 shares of GE in 2020 that he bought in 2000, he can look forward to 86 years of tax losses carried forward.

Dan Smith
3 hours ago

You give a good definition of “loopholes”. I think they’re real. I sort of think that excluding Roth distributions from AGI may have been unintended, and therefore a loophole. Also, those back door Roth conversions probably fit the definition of loophole. But what politician has the guts to close them. 
There are other loopholes, but that kind of thing is way above my pay grade. I bet the CPAs could add a thing or two.
All those other credits and deductions you list seem to work as intended, so I wouldn’t consider those loopholes. 
Here’s an interesting loophole I came across on the internet. The Augusta Rule, (Section 280A(g)). It allowed people in Georgia to rent out their home for up to 14 days (during the golf tournament) without having to declare the income on their taxes. The unintended part happens when the owner of an S-Corp rents his personal home to the corporation for the annual board meeting, or maybe a personal retreat. He gets the tax free income, The S-Corp gets the tax deduction.

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