A jailed Italian who tried to sell a ‘fake’ Rolex in Singapore is the wildest watch story ever

In a single afternoon, a 24-year-old Italian man in Bencoolen managed to commit what lawyers actually call an “impossible attempt,” which is the legal version of attempting to pick an empty pocket.

The short version: He set out to defraud a watch dealer in Singapore by selling him a fake Rolex GMT Saruexcept that the watch was not a fake. It was the real thing. And he’s now serving seven months in prison in Singapore because of it.

Here is what happened….

The entire saga, reported by Channel News Asia after Monday’s verdict, reads less like a white-collar crime and more like a cautionary tale about buying reputable watches from a guy you sort of know.

Singh picked up the Saru in early 2025 from an acquaintance known only as “Matteo” and gave him €55,000 in cash and a Cartier bracelet worth €5,000 for a piece he said was worth about €90,000 on the resale market.

For those who have no preference for Rolex models not available in the catalog: the GMT Saru is one of those quiet references: set with precious stones, extremely limited, supposedly there are only around 20 authentic pieces. The kind of watch that, if real, will make your year. If it is fake, your lawyer’s year will be displayed.

Singh’s friends told him to get it checked. A watch store took a look and spread the worst-case theory in the off-catalog Rolex universe that the case may have been replaced and a real serial number laser engraved on the replacement piece. At this point, the clock was cooked in his mind. So he did what anyone with questionable judgment and a return flight would do. He decided to brush it off.

On November 27, 2025, he flew to Singapore with friends and planned to flip the Saru and get out with other Rolex models that he could resell in Europe. The next afternoon he marched to the Watch Room in a shopping center in Bencoolen with the watch and warranty card, sat down with the 32-year-old director and began negotiating.

This is where things get really angry. The dealer took a look and identified the Saru as an off-catalogue Rolex worth about S$120,000. They agreed on S$94,700. Singh didn’t want a bank transfer. He wanted watches. Specifically, these are a Rolex Daytona (S$25,200), a Rolex GMT (S$25,400) and a Rolex Submariner (S$44,000). The dealer even threw in an additional S$300 because Singh didn’t get any boxes.

Before the deal was finalized, the retailer did what any reputable retailer does. He saved the warranty card, ran a UV flashlight over it, checked the labeling, inspected the watch and called his buddy. Everything came back clean. Singh handed him a doctored copy of his passport, “Sinsi Deepak,” a doctored number, the kind of amateur forgery that works until it doesn’t work anymore. And he walked out with three Rolex watches that he knew had been purchased as a counterfeit.

Except the watch was real.

After Singh left, the dealer took the Saru to neighboring shops for a second opinion. One of them handed him a magnifying glass and told him to take a close look at the serial number. The engraving looked. Washed off and then lasered again. Classic Franken-Rolex warning sign. The dealer called Singh. Singh, now panicking and still thinking he had just dumped an unexploded ordnance, picked up, promised to come back, and then disappeared. He booked a 10pm flight to Rome via Helsinki and flew to Changi.

The dealer called the police. The police were at Changi first. Singh was arrested before boarding.

Then came the plot twist.

Singapore Police took the Saru to the Rolex Service Center. A technician inspected it and certified each part as authentic and original. The watch that Singh was convinced was a fake, the watch he had flown abroad to empty, the watch he had forged his passport for, was the real watch. He could have sat on it, sold it openly in Europe and made a tidy profit. Instead, he had simply tried to cheat a man out of three genuine Rolex models using a Rolex that didn’t need to be cheated.

This is what lawyers love. Under Section 511(3) of the Singapore Penal Code, an “impossible attempt” is still an offense if the intent and acts are present, even if the underlying offense could not actually be committed. You wanted to cheat. You did everything to cheat. The only reason no one got scammed is because of a fact you didn’t know. Guilty.

Assistant Public Prosecutor Sean Teh pushed for 12 months, arguing Singh followed the fraud to completion and then took it to the airport. His lawyers at LVM Law Chambers sought six sentences, citing the fact that no actual harm was caused, that it was a first offense and that Singh’s parents, a housekeeper and a cook, who together earned less than S$2,300 a month, could not afford to fly 13 hours from Italy for a visit. The court ended up with seven months. Singh pleaded guilty to one count of attempted fraud. A second charge relating to the tampered passport was being considered.

And you see, there is no understanding of the attempted fraud here. The dealer did everything right. UV flashlight, warranty check, a second pair of eyes, a magnifying glass as soon as doubts arise. That’s the job. The reason this hurts so much is the sheer avoidability. Singh had a genuine Rolex GMT Saru. In this corner of collecting, that’s a lottery ticket. He simply didn’t trust him, didn’t receive proper authentication, and instead panicked his way into a Singapore jail cell.

If there’s a lesson for the rest of us, it’s an old man wearing a very expensive suit. Shop the seller before buying the watch. Get it authenticated by someone who actually knows the reference, not a WhatsApp friend and a shop shrugging their shoulders. And if you’re ever convinced your Rolex is a fake, maybe don’t book that 10pm flight from Changi until you’re really, really sure.

Hand on heart, this is the wildest watch story this side of 2026.