Eleven years ago, Lai Kah Goon was part of a group that scammed car rental companies in Singapore by renting cars from them and selling them in Malaysia .
Lai fled the country, stalling police investigations into the scam which involved four cars worth $355,250 in total.
The need to pay off his debts to loan sharks then led him to traffick drugs from Malaysia to China.
He was deported back to Singapore in May 2010, after serving a six -year jail term in China.
Yesterday, Lai, now 50, was the first of the group to be punished for the 2004 scam .
He was jailed for 32 months, after pleading guilty to two counts of cheating and dishonestly inducing the delivery of property. Another two counts of the same charge were taken into consideration.
In passing sentence, District Judge Low Wee Ping said: "These car rental companies... cannot tell whether a customer renting its car is genuine, or a person like yourself, intending to rent the car and instead drive them to Malaysia and then sell them."
"It is alarming because it sounds so easy," he added.
The judge also noted that the level of planning involved in the scheme was "quite sophisticated".
"Unless there is a strong deterrent sentence, others will attempt to commit such offences," he added.
On one occasion, in December 2004, Lai was told by an alleged accomplice, Koh Choon Siong, 40, to rent a car from L&K Limousine Services. Koh allegedly drove the car to Malaysia and handed it over to two alleged conspirators, Steven Koh Chin Guan and Alvin Ng, who purportedly sold the vehicle, valued at $85,250, to unknown buyers.
Lai rented another car, worth $120,000, from Motorway Car Rentals on the same day, and Koh Choon Siong allegedly delivered it to the same alleged conspirators the next day.
Lai did not receive any money from the car sales. He said he was given $5,000 by Koh Choon Siong to use for renting cars, and allowed to keep the balance.
In calling for a stiff sentence, Deputy Public Prosecutor Loh Hui-Min said: "A strong signal should be sent to the general public that such offences will not be tolerated."
Pleading for leniency, Lai's lawyer Gogulakannan Suppayya said his client owed money to loansharks who "continuously harassed his home and his two young children then".
Lai admitted to his offences and has shown remorse, he added.
Mr Gogulakannan said Lai, who is divorced, works as a driver earning $1,750 and pays monthly maintenance to his former wife, and children, now aged 14 and 19.
Lai could have been jailed for seven years and fined for each charge.
Koh Choon Siong's case will be heard on Aug 5.
Steven Koh Chin Guan and Alvin Ng remain at large.