We all have our stories about audits from hell.

I’ve had cases where auditors refused to meet with me and disallowed all of my client’s business deductions. We had to go to court, where we easily won every issue -- except for the cost for my poor client.

I’ve even had a case where an auditor took my client’s Law Diary and removed stapled substantiation. Fortunately, Appeals noticed the staple holes.

But, in over 40 years in the tax business, one audit stands out as my worst.

I was a young attorney, going to battle with the revenuers for an elderly, but feisty taxpayer. I had gone to a few audits before but was still learning the ropes.

As we sat down, my client moved closer to the auditor, a middle-aged woman. “I bet you $100 that I can bite my eye,” he said.

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Before she could respond, he took out a false eye, put it in his mouth, and bit it. “You owe me $100,” he shouted. As the auditor was about to get up and call the police, the client gave her a chance to get even.

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“Bet ya I can bite my other eye!”

I looked at the auditor and pleaded to get back to why we were there. She didn’t want to get into an argument as to whether she actually made the bet. She figured, clearly, the client wasn’t blind. She figured he couldn’t have two false eyes.

She didn’t figure on his pulling out his dentures and biting his other eye.

“One last chance,” he offered. There was a coat rack two feet behind her desk. My client bet $1,000 that he could stand on a chair, urinate over her desk and hit the coat rack.

Before we could stop him, there was a stream, all of which landed on the auditor’s desk.

My client then handed six crisp $100 bills to the auditor. This audit was over. I immediately called a stop to it and suggested the client find another representative.

Why was this my worst audit ever?

Prior to the meeting, my client was beyond confident of victory. He had bet me $5,000 that, before the audit was over, he’d urinate on the auditor’s desk and she’d be happy about it.

Related reading:

• Tax deductions that shout ‘Audit me!’
• Tax records you can toss
• IRS to expand audits as cash runs low