He Traded $164,000 for $20

Case File #044: Rockville, MD. 1988. Tony's camera caught it all.

Apr 26, 2026

private investigator story insurance fraud

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I’m not sure how the file got to our office or even how much work Tony had already done on the case. Insurance fraud. The subject had been awarded $164,000 in a settlement. That’s 1988 dollars. About $446,000 today. Not small money.

Insurance companies, as we all know, hate losing cash.

Tony had been tasked with doing a follow-up visit about six months after the settlement. I don’t remember all the details because I wasn’t lead on this. I was the lowest rung of a tall ladder of investigators at our place.

Tony issued a command as he walked by me: “Get your stuff. You’re coming with me.”

So I did.

We drove about four miles to a Rockville, MD grocery store and pulled into a parking space, head out. The temperature was hot, so we rolled the windows down. I’m just glad the sun was to our rear, not glaring into the windshield.

“See that green Chevy? That’s the subject’s car,” Tony said, pointing to the next row of cars in front of us, one car to our right.

Tony put up one of those whole-window sunshades, the kind that blocks out the entire windshield. Only this one had a homemade flap that moved side to side. Pretty clever, really.

Tony was good at what he did. He knew cameras. In fact, it was Tony who showed me how to take great pictures from long distances in any kind of light of people doing things they probably shouldn’t be doing. Those skills later translated into some pretty high-end sports photography for me. Whole other story.

He handed me a photograph. White male, scruffy dark brown hair, brown eyes, unfortunate mustache.

“Your pretense is buying groceries. But here’s the real deal. The subject works behind the high counter next to all the registers. Take a good look at this.”

I studied the photo.

“When he goes to leave, I need you to follow. I’ll be watching, but just in case, when you come out of the store behind him, look my way and tip that chicken hat of yours,” Tony teased.

Jayhawk. I keep telling you, Jayhawk, I think to myself.

Everyone from out East has no idea there’s land west of the Ohio River until they land in Los Angeles. And don’t even get me started on New Yorkers.

“Be quick,” Tony added. “He gets off in about ten minutes.”

I walked up and down the aisles, half paying attention to what pasta sauce I was adding to the cart. Then I saw mustache man, getting ready to leave. Right on time. Neck brace and all.

Still wearing a neck brace? I really should have learned more about this case.

But then he does something unexpected. He grabs a basket and starts shopping. Slowly. Eight or ten items later, he finally leaves the freezer section for the checkouts.

I abandoned my cart, grabbed an empty checkout next to him, and paid for a Coke and a Heath Bar I picked up from the last-minute candy section. I love the crunch of the toffee.

Don’t judge. I was still young.

He exited the grocery store at a loafer’s pace, carrying one very full brown paper bag.

It’s hard for me to walk that slow. But I adjusted. Exited the sliding door. Tipped my hat in a half-wave sort of fashion.

Even thirty or forty yards away, Tony and I made eye contact.

He was smiling.

As I was instructed, I stayed about ten or twelve yards behind and went to the second car from Tony. Ostensibly, looking for my keys while watching our subject the whole time.

Ah. Now I see it.

There were two rolls of quarters just under the driver’s door of the subject’s car. One roll intact. One roll broken open, scattered in a small area.

Bait.

Easy enough to see. But you’d have to reach down to get them.

And he did.

Dude reached down while holding the paper bag. But not before looking around to see if anyone else had noticed. And I mean a full side-to-side neck turn. The guilty-looking kind.

It was just too good.

This guy was bent over, neck brace on, holding a bag of groceries, picking up quarters and throwing them in the bag, and still looking from side to side as if he was stealing the Hope Diamond.

I never learned all the ins and outs of this case. I filled out a report and moved on. But I was told the insurance company loved the video Tony provided to them. Permanently disabled guy from an accident (allegedly), bending over and straining himself for $20 while holding weight in one arm. (Here I would also say “allegedly” but not for the fact that I was there and I know what I witnessed.)

I don’t actually know if the insurance company recovered any money. That’s true. I wasn’t part of the recovery. Lawyers and insurance types don’t circle back to keep us updated.

But I know he lost that $164,000 settlement for twenty bucks in twenty-five cent increments. No way the insurance company was letting that slide.

Because Tony was in his car, flap to the side, videotaping every bit of what went on.

$20 in quarters cost this guy $164,000.
What’s the smallest thing you’ve ever seen someone lose something big over?
Tell me your version.

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