A lawyer just lost a Tax Court case—because he trusted AI to do his legal research.

He used AI to write his brief, submitted it with fake case citations, and the Tax Court wasn’t amused. He lost.

Here’s the reality about AI tools (ChatGPT, Claude, Perplexity, all of them):

AI doesn’t think. It predicts words based on patterns—not truth. It has no fact-checker.

General AI tools hallucinate 58% to 82% of the time on legal questions. Even legal-specific AI tools still get it wrong 17% of the time.

Tax law is particularly brutal for AI because it’s complex and constantly changing.

What this means for contractors:

Don’t trust AI for tax strategy, legal advice, or contract decisions. AI can assist your thinking, but it can’t replace real expertise.

Use AI as a tool. Not a substitute for your CPA.
I’ve personally noticed a lot of my calls, with both clients and prospects, have become higher in quality of conversation, and I’m all for that. But like any other tool, AI research has its time, place and limitations.



Disclaimer: This content is provided for educational purposes only and is not legal, tax, accounting, or financial advice. Every situation is unique, so consult your own attorney, CPA, or financial advisor before making decisions based on this information.