Back with a new story today. Enjoy! — Dan

If you’ve ever bought something second-hand — something valuable, like a car or jewelry or maybe (if you’re me) baseball cards, you may often feel some sense of buyer’s remorse. Self-doubt creeps in as you wonder if you paid too much, and if the seller knew something about the product that you didn’t. You may even investigate further — and if you find out that your feelings of doubt were well-founded, you may take actions to correct it.

But doing so may send you to prison — even if your doubts turned out to be wrong.

In early 2025, a 24-year-old Italian man named Deepak Singh bought a rare Rolex GMT "Saru" — a gem-set, off-catalogue model — from an acquaintance known only as "Matteo." As The Straits Times reported, Singh handed over €55,000 in cash (about $60,000) plus a Cartier bracelet worth about €5,000 in exchange for the watch. It was a good deal — the watch typically sells for about $93,000 — so Singh decided to get it appraised, just to be sure. One appraiser told him that the serial number on his watch "may have been laser engraved," a classic sign of a counterfeit. Singh concluded that Matteo had cheated him.

So he decided to make it someone else's problem.

On November 27, 2025, Singh flew to Singapore, and the next day he walked into a shop called The Watch Room in Bencoolen Mall. According to Singaporean news site Mothership, the shop's director, thinking the watch was real, agreed to buy it for the equivalent of about $73,000. Singh made a counteroffer, trading the watch for three lesser-valued ones and some additional cash, but looked like he was going to walk away even at worst. For the shop's records, he handed over a soft copy of his passport. It was forged, complete with an AI-modified photo.

Singh left with the three watches and the shop director similarly became suspicious of the watch he just bought. He, too, investigated, and had similar reason to believe that the Saru he just acquired was fake. So the shopkeeper contacted Singh and asked him to undo the deal. Singh agreed by phone, and promised to come back to the shop — but then booked a flight to Italy, hoping to escape and leave the fake watch behind. Those hopes failed, though. The shopkeeper contacted authorities and Singapore police said that officers tracked him down at Changi Airport within three hours of the report and recovered all three Rolexes. The police announcement described what Singh had handed over as a "counterfeit luxury watch," and the press reported it that way, too.

There was just one problem with that.

On December 3, police brought the Saru to the Rolex Service Centre, where a technician certified that every part of it was authentic and original. The watch was real.

But as far as Singapore law was concerned, that didn’t matter. According to section 511 of the country's Penal Code, "a person may attempt the doing of a thing despite the existence of facts of which he is unaware which make the doing of the thing impossible,” and that applied here. The prosecutor noted that Singh "followed through with his attempt to cheat the victim to completion." Singh pleaded guilty to attempted cheating, and on April 20, 2026, he was sentenced to seven months in jail. Hopefully, he had a watch to help him count down the time served.

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Today’s Bonus fact: A Rolex helped a used car salesman get a job — as James Bond. When Sean Connery walked away from the role after You Only Live Twice, an Australian former car salesman and model named George Lazenby decided he wanted it. As MovieWeb recounts, he bought a suit from a London tailor, purchased a Rolex, and went to Connery's barbershop to get the Bond haircut. He wasn't on the list of contenders, so he waited for the receptionist to get distracted — "I just bolted past her up the stairs," he later said — and handed the producers a resume listing acting roles in Germany, the Soviet Union, and Eastern Europe, none of which existed. Lazenby eventually confessed to director Peter Hunt that he'd never acted at all, and Hunt reportedly laughed it off and kept him. Lazenby starred in 1969's On Her Majesty's Secret Service — and then quit after one movie.

From the Archives: Why You Might As Well Steal That Rolex Off Your Murder Victim: Also a real Rolex. Also didn't end well.

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And thanks! — Dan