And now he is doing time behind bars for his interactions with Lady Luck.
The 20-year-old was captured on video cameras at the stores, not long after an early morning Sept. 24 robbery at a Wellington Street West confectionery, where two suspects made off with $993 in lottery tickets.
City police were contacted by a cashier at the Mac's Mart at 7:30 a.m., who indicated that the pair had demanded cigarettes and lottery tickets, a judge heard Monday.
A search of the area resulted in no suspects, but officers contacted the OLG ( Ontario Lottery and Gaming Corporation) and asked it to track the tickets.
The police were provided with a list of the tickets, which had been been redeemed at other businesses, and surveillance videos indicated Roy was the person who checked and cashed them in, prosecutor Robert Skeggs said.
Ontario Court Justice Melanie Dunn was told he received $45 winnings at a gas bar, $6 at a market, $150 at one convenience store and $82 in winnings at another.
Roy pleaded guilty to possession of stolen property (the tickets), theft under $5,000 stemming from an August incident where he was nabbed with $119 in stolen meat outside a Second Line West Metro store, breach of probation and two counts of failing to comply with a recognizance.
Dunn sentenced the young man, who has been in custody, to a further seven months incarceration — a joint submission put forward by the prosecution and the defence.
With the time he has already spent in jail on the charges, the sentence is the equivalent of a 15-month term.
Defence counsel Jennifer Tremblay-Hall noted a more serious charge of robbery in connection with the lottery tickets was being withdrawn because there was not enough evidence.
Roy is a youthful offender, who has serious addiction issues, is remorseful and has taken responsibility for his actions, she said.
Since he has been in custody, he "is clean and feels better," Tremblay-Hall said, adding this is his longest period of sobriety since he was a young teen.
The sentence might seem like a significant one, but it takes into account his history with the justice system during the past year, she told the court.
As well, it "balances denunciation and deterrence with rehabilitation."
Skeggs said the young man has a limited record, but suggested there were "concerning facts."
"The tickets were cashed a short time after the robbery," the assistant Crown attorney said.
When she imposed sentence, Dunn said she was accepting the joint submission, which is in the range, in light of the withdrawal of some significant charges.
In addition to the further seven-month jail time, the judge placed Roy on probation for 12 months, with conditions that require him to stay away from the Metro store and the Wellington West Mac's and undergo counselling.
He must also provide a DNA sample for the national database.
"I hope you use the next seven months wisely, something education-wise or counselling," Dunn told him.
"I've already started school," Roy replied.
"Good for you," the judge said.
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