When he tripped over his own ankle cuffs or first took the stand to give evidence, he smiled. When faced with press photographers and eager crowds who queued up at the High Court hoping to catch a glimpse of him, he smiled.
Embroiled in one of the most sensational murder cases that gripped Singapore and attracted wide publicity, he gained overnight infamy and seemed to relish in his newfound notoriety.
His smile was his trademark, a secret weapon, one that hid the 35-year-old graphic designer's devious intentions and was used to charm people in his life into doing his bidding.
But eventually, Lady Luck stopped smiling at Anthony Ler.
In April 2001, Ler approached four youths and dangled a reward of $100,000 to kill Madam Annie Leong, a 30-year-old insurance agent. The couple were in the midst of divorce proceedings. Only the youngest boy, a 15-year-old whom Ler had known for five years, took up the offer.
A master manipulator who orchestrated the plot with calm precision, Ler played on the teen's emotions to do his dirty work. He coached his juvenile accomplice on how to execute the hit cleanly, taunted and belittled him when he tried to back out, and finally forced him to go through with it by threatening to kill him. When Madam Leong sepaseparated from Ler in 1999, he was deep in debt after failed business ventures and had been out of a job for two months.
He had also lost his meagre savings on horse-racing bets.
He stood to gain sole possession of their $480,000 Pasir Ris matrimonial flat and custody of their four-year-old daughter from her death.