The phrase that should worry every non-tax lawyer

You sparked a robust debate on Threads by saying that tax law touches everything. What's a practice area where lawyers consistently underestimate how much tax law is hiding inside their cases?

Litigation. Especially family law, personal injury litigation and criminal defense.

In family law, attorneys are routinely dealing with property transfers, business interests, retirement accounts, support obligations and dividing assets that may have very different tax consequences. Two settlement agreements can accomplish the same family law objective but leave clients in very different financial positions after considering the tax impact.

Personal injury litigation is another big one. Attorneys are great at negotiating the value of a case, but the tax treatment of the recovery itself can sometimes become an afterthought. For example, damages received on account of physical injuries or physical sickness are treated differently from punitive damages or other types of recovery. The way a settlement agreement allocates those amounts can matter.

Criminal law also has hidden tax issues. A lot of people are surprised to learn that illegally obtained money can still be taxable income. If someone steals, embezzles or otherwise obtains funds unlawfully, there may be tax reporting obligations associated with that money. If restitution or repayment happens in a later year, that creates an additional layer of tax analysis because different compliance rules may apply.

That’s what I mean when I say tax touches everything. The tax issue is often not the main legal issue a lawyer is hired to solve, but ignoring it can create an entirely separate problem for the client.

What should a non-tax attorney ask themselves before they accidentally create a problem?

“Am I making an assumption about how this will be taxed?”

If you catch yourself saying things like “that probably isn’t taxable” or “they shouldn’t owe anything,” that is usually a sign you need to confirm before moving forward.

A lot of tax problems do not happen because someone intentionally ignored the law. They happen because either no one realized there was a tax question that needed to be asked, or assumptions were made.

My favorite question is: "Did anyone receive, give away, sell, forgive, transfer, or inherit something of value?" If yes, pause.

Even if your client has already talked to their accountant?

I love accountants, but tax compliance and tax controversy are different worlds. Preparing a return, defending a position before the IRS and analyzing legal consequences are not always the same thing.

When a client says, “I’m just transferring this property/business/money to…” coupled with “My accountant, tax preparer, etc., said it was fine,” I’m on high alert. 

How are you using AI in your practice? 

Through my work with VITA and my community service with Sigma Gamma Rho Sorority, Inc., I saw firsthand that access to information does not always mean access to understanding. My job is not just to understand the tax law; it is to communicate it in a way that allows people to make informed decisions.

AI is great for simplifying explanations and helping translate complicated concepts into client-friendly language.

Where I don't trust it is legal authority. In my experience, ChatGPT is actually pretty weak when it comes to tax law. When I'm testing it, I often have to walk it through the legal analysis before it arrives at the correct conclusion. That's exactly why it's risky for someone without a tax background to rely on AI for tax advice—they may have no way of recognizing when the answer is wrong.

What's the one tax-law development every attorney (not just tax attorneys) should have on their radar?

The issue I am watching closely is whether certain Tax Court filing deadlines, particularly the 90-day deadline to file a petition after a Notice of Deficiency, are jurisdictional or whether they are claims-processing rules that may be subject to equitable tolling.

Historically, practitioners treated that deadline as a hard stop. But after the Supreme Court's decision in Boechler, which held that the deadline for certain Collection Due Process petitions was not jurisdictional and could be subject to equitable tolling, courts have been forced to look more closely at other Tax Court deadlines.

This matters beyond tax because the question is bigger than one Internal Revenue Code section. It impacts how courts interpret filing deadlines, when equitable relief may be available and whether a missed deadline automatically eliminates a client’s ability to be heard. The best facts in the world do not matter if your client never gets through the courthouse doors. 

Bonus round: If someone wanted to get a feel for being a tax attorney, what movie would you suggest they watch? 

One of my favorite tax-adjacent movies is The Accountant. Beyond the action storyline, I love that it highlights something people often overlook: numbers tell stories. Financial records can reveal what happened long before anyone gets the chance to explain it.

That is actually one of the things I find most fascinating about tax work. Whether it is a business dispute, criminal investigation or IRS controversy, the numbers usually tell a story—my job is figuring out what story they are telling and how I can honestly frame it in my client’s favor.

(Image courtesy Chavioleyette Fenelus)