Five Questions With Stinson Tax Partner Harry Teichman

Bloomberg Tax Insights & Commentary is featuring a recurring questionnaire of prominent tax professionals who are willing to share their thoughts about their work and the practice of tax these days. Today we feature Harry Teichman, a tax, corporate and estate planning partner at Stinson in Tampa, Fla.

What is the biggest challenge that tax practitioners are facing in 2026?

If you don’t answer AI, you aren’t paying attention. AI research tools are rapidly becoming the front line of efficiency when clients evaluate work product and how long it takes to respond.

Sure, AI might produce a quick answer that seems right, but is it technically correct? So far, I wouldn’t want to be a batter with that average. While learning how to leverage these tools, practitioners must keep in mind that clients are paying for rigorous analysis and professional judgment.

What tax case is no one watching that they should be?

HDH Group, Inc. v. United States in the US District Court for the Western District of Pennsylvania. This case involves civil fraud tax penalties assessed under IRC Section 6700 and raises the question of whether taxpayers are entitled to a jury trial before the IRS imposes penalties.

Following SEC v. Jarkesy, there is a circuit split emerging. The Pennsylvania court held that taxpayers can receive a jury trial in a de novo district court refund suit after paying part of the penalty, which satisfies the Seventh Amendment. However, in United States v. Sagoo, the Northern District of Texas held that penalties must be considered by a jury before assessment.

The stakes are significant and get to the heart of whether federal agencies can unilaterally impose civil penalties without violating constitutional jury trial rights. Mark my words: We’re going to see this issue before the Supreme Court.

What tax issue keeps you up at night?

Partnership audits under the Bipartisan Budget Act of 2018. It fundamentally changed how partnership audits work, replacing the old procedures under the Tax Equity and Fiscal Responsibility Act of 1982 with a centralized regime that generally assesses and collects tax at the partnership level.

The statute has left many critical questions unanswered: how adjustments flow through tiered partnership structures, how to properly compute imputed underpayments, and what happens when partnerships cease to exist or go bankrupt. Even basic mechanics such as the modification process and how tax attributes should be accounted for in intervening years remain unclear eight years later.

The stakes for partnerships and their partners are enormous—we’re talking about potential liability shifts where current partners may end up paying tax on income earned by previous partners—and the lack of clarity is keeping a lot of us in the tax bar awake.

What’s the most memorable case you’ve worked on?

My case against the State of Florida in MiCJO LLC. It was just me, on my own, against the Florida Attorney General’s office regarding the Florida tobacco excise tax.

The case turned on a seemingly simple question: Does “wholesale sales price” for purposes of Florida’s 85% Other Tobacco Products tax include only the manufacturer’s price for the tobacco itself, or the entire invoice, including federal excise tax reimbursements and shipping charges?

The Florida Department of Business and Professional Regulation insisted it meant the whole invoice, which, of course, generated more tax revenue for the state. I argued the statute’s plain language said otherwise, and Florida’s Second District Court of Appeal agreed.

The decision became a landmark ruling that set the tone for tobacco tax litigation nationwide and opened the door for distributors across the country to file refund claims. I won—and then they changed the statute. I suppose that’s one way to respond to losing.

What’s the biggest lesson you learned in your early years of practice?

Read the statutes and regulations first, then the cases, then the treatises. Make up your own mind about what the tax code and regs say before you let someone else tell you what they mean. You’d be surprised how often the answer is right there in the text if you take the time to look.

This article does not necessarily reflect the opinion of Bloomberg Industry Group, Inc., the publisher of Bloomberg Law, Bloomberg Tax, and Bloomberg Government, or its owners.

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