The IRS Commissioner Problem: Anthony Parent on Tax Court, 1099-DA Chaos, and AI

About this episode

Clinton Donnelly discusses the implications of the IRS operating without a Commissioner with guest Anthony Parent, covering tax court issues, crypto tax reporting, and the role of AI in tax law.

Is the IRS operating without a real Commissioner, and could that create problems for Tax Court cases, IRS appeals, and crypto tax enforcement? In this episode, Clinton Donnelly speaks with Anthony Parent of IRSMedic about the IRS Commissioner problem, Tax Court authority, IRS delegation orders, and what may happen when enforcement continues without clear leadership at the top. Anthony explains why he filed a motion to vacate in U.S. Tax Court, why he believes the absence of a Commissioner of Internal Revenue may create structural problems, and how this could affect certain IRS collection and Tax Court matters. The conversation also covers Form 1099-DA and the crypto tax reporting problems expected in 2026. Clinton and Anthony explain why 1099-DA may confuse taxpayers, why gross proceeds do not equal taxable income, and why missing cost basis could trigger IRS mismatch issues or CP2000-style notices. They also discuss AI in tax law, why tools like TaxGPT can produce confident but wrong answers, and why tax professionals who use AI lazily may create serious problems for their clients. Anthony Parent is the founder of IRSMedic and helps taxpayers with complex IRS, offshore…

People in this episode

Host: Clinton Donnelly

Guest: Anthony Parent

Topics covered

• IRS Commissioner
• Tax Court
• crypto tax enforcement
• Form 1099-DA
• AI in tax law
• IRS collection
• taxpayer confusion

Keywords

• IRS
• Tax Court
• crypto tax
• Form 1099-DA
• AI in tax
• taxpayer confusion
• IRS enforcement
• tax professionals
• CP2000
• tax controversy

Mentioned in this episode

Organizations: IRSMedic, TaxGPT

Products: Form 1099-DA

Places: U.S. Tax Court

More episodes of The Clinton Donnelly Show

• 1099-DA Disaster: Why Crypto Taxpayers Still Don’t Know What to Report · June 9, 2026 · 7 min
• What I Learned at the IRS Conference About Crypto Reporting · June 2, 2026 · 6 min
• Should the IRS Offer Crypto Tax Amnesty? Crypto Traders Need to Speak Up · May 28, 2026 · 2 min
• Kalshi & Polymarket Taxes: Can You Lose Money and Still Owe Tax? · May 22, 2026 · 5 min
• Your 1099-DA Could Make It Look Like You Made $1 Million · May 19, 2026 · 4 min
• Why Is My 1099-DA So High? Crypto Tax Strategy for Traders · May 12, 2026 · 3 min