An Italian man flew to Singapore to offload what he believed was a counterfeit Rolex, traded it for three genuine luxury watches, and then tried to flee the country. The only problem: the watch he thought was fake turned out to be completely real.
Deepak Singh, 24, was sentenced to seven months in jail on April 20 after pleading guilty to one count of attempted cheating. As Malay Mail reported, a Rolex Service Centre technician later confirmed every component of the watch was authentic and original, turning the case into what prosecutors described as an “impossible attempt.”
How Singh ended up trying to sell a watch he thought was worthless
The saga started in early 2025 when Singh purchased a Rolex GMT-Master II “Saru” from an acquaintance known only as “Matteo.” He paid €55,000 in cash and handed over a Cartier bracelet valued at around €5,000, expecting to flip the watch for around €90,000 on the resale market.
The Rolex GMT Saru is an off-catalogue model. Only about 20 authentic pieces are believed to exist in the world, making it one of the rarest Rolex references in circulation.
Before trying to sell it, Singh got cold feet. Friends warned him the serial number looked suspicious, and a watch shop he visited raised the possibility that the case may have been swapped and the serial number laser-engraved onto a replacement. At that point, Singh concluded he had been scammed and was holding a worthless fake.
So he flew to Singapore on November 27, 2025 with a plan: unload the “fake” and walk away with real watches he could resell back in Europe. This kind of scam isn’t unheard of in the watch world. Scammers dressed as a bear to trash a Rolls-Royce but cops noticed fast, and elaborate deception schemes regularly backfire in spectacular fashion.
A forged passport, three Rolexes, and an airport arrest
The next afternoon, Singh walked into The Watch Room, a shop in The Bencoolen mall. He offered the Rolex GMT Saru and its warranty card to the shop director, asking for a trade rather than cash. He walked out with three genuine Rolex watches, a Daytona, a GMT, and a Submariner, valued at around S$94,700 (approximately $71,000 USD).
To hide his identity during the transaction, Singh provided a forged passport copy under the name “Sinsi Deepak,” with both his photo and passport number altered.
After Singh left, the shop director noticed the same suspicious signs around the serial number and sought second opinions from nearby retailers. Convinced the watch was a fake, he called the police. Singh ignored the calls, booked a late-night flight to Rome via Helsinki, and headed to Changi Airport. Officers from the Central Police Division tracked him down and arrested him at the terminal before he could board. All three Rolex watches were recovered.
The twist that made this case legally strange
What happened next is what made this case unusual. When police sent the watch to the official Rolex Service Centre on December 3, 2025, a technician certified that every single part of the timepiece was genuine.
Singh had not scammed anyone. He had actually given a real watch worth S$89,800 and received three watches valued at roughly the same amount. No actual financial loss occurred. The whole scheme had been logically impossible from the start.
Still, prosecutors argued Singh’s intent was what mattered. “This was an accused who followed through with his attempt to cheat the victim to completion,” Deputy Public Prosecutor Sean Teh told the court, noting Singh never voluntarily backed out of the scheme. The prosecution sought a 12-month sentence.
Singh’s defense lawyers pushed for six months, describing him as a first-time offender from a working-class immigrant family in Italy. His parents, a housekeeper and a cook, could not afford to travel to Singapore during his detention. The court settled on seven months. It’s the kind of bizarre story that sticks with you, not unlike the Cowboys fan who showed a cheerleader’s husband an entire phone album of her and somehow thought that would end well.
Under Singapore law, cheating carries a maximum penalty of ten years in prison and a fine. Singh’s charge was reduced to attempted cheating given the impossibility of completing the offence.
