He robs foreigner after losing at gambling
Teen gangs up with friends to target two victims in Geylang
Having gambled away his money, he decided to recoup his losses by robbing people.
First, he and two friends beat up an Indian national and made off with the man's wallet, mobile phone and other valuables.
Later that month, he snatched the handbag of a man who was dressed as a woman.
But the law eventually caught up with Alson Chew Guozhi, 17, who committed the crimes while on probation.
Yesterday, Chew was sent for reformative training on one count of snatch theft and another of robbery.
On Nov 10 last year, Chew and two friends, Daryl Ng Zhong Jun, 16, and Keith Tan Kai Wen, 17, went to Lorong 16 Geylang to gamble.
After losing money, they decided to rob a foreigner to cover their losses.
They spotted their first victim, Mr Govindaraj Tamilventhan, 28, an Indian national who had been working here as a civil engineer for four years.
He appeared drunk and looked an easy target.
At 11.10pm, Chew approached him and asked him if he wanted a "girl", by which they understood to mean a prostitute.
After Mr Govindaraj agreed, Chew and his friends led him to a staircase at Lorong 16 Geylang, where they asked him for money.
But he insisted on seeing the "girl" first and tried to leave.
Chew, who was on 18 months' probation for unlawful assembly, pushed Mr Govindaraj against a wall while Ng grabbed his shoulder.
Chew punched the man several times while Ng kicked him.
After Mr Govindaraj fell to the ground, they grabbed his wallet, containing $1,200 and other valuables, from his back pocket and a Samsung Galaxy Tab, worth $600, from his hand and fled.
Then, at midnight on Nov 27, Chew went to Geylang again to gamble - this time with Benjamin Tan Han Wei, 20.
After losing $300 at a dice game, Chew again suggested they rob someone.
They spotted Mr Zulkiflee Rahman, 23, who was dressed as a woman, at Lorong 16 Geylang, court papers said.
Chew approached him and pretended to be interested in engaging his sexual services.
Chew lured him to a hotel at Lorong 22 Geylang. As Mr Zulkiflee was about to walk into the hotel, Chew snatched his handbag, containing cash and valuables worth $300, and fled.
Benjamin Tan, who was nearby, ran in a different direction but was apprehended by a passer-by.
Chew was arrested the next day and confessed to the earlier robbery to the police.
Court papers said Mr Zulkiflee was given back $200, and Mr Govindaraj was paid $2,100 by Chew and his friends.
Those given reformative training spend between 18 months and three years in a reformative training centre, where they do foot drills and undergo counselling.
The cases against Chew's three accomplices are pending.