The offender, now 21, was the sole adult among four people charged in the controversial and much-publicized hazing case at the esteemed St. John's-Ravenscourt School.
He previously pleaded guilty to six counts of assault with a weapon. He was 18 when the assaults took place between September and December 2009. Sexual assault-related offences and other charges were dropped.
The man, who can't be identified to protect the identity of the victims, admitted he wielded a wooden stick to assault six younger boys ranging in age from 14 to 16.
On five occasions, the boys were jabbed in the buttocks for a matter of seconds after they were forcibly held down.
There was no penetration but victims were left "embarrassed and fearful," Crown attorney Nancy Fazenda told Judge Janice leMaistre during a lengthy sentencing hearing Friday.
Fazenda asked leMaistre to send the man to jail for an unspecified period of less than two years in hopes of sending a message acts of bullying won't be tolerated.
"These were not opportunistic offences," said Fazenda. "They were planned. They were deliberate."
Three youth co-accused have already dealt with their charges and received community-based sentences.
Defence lawyer Sheldon Pinx asked for a discharge with probation for the offender so his future career prospects aren't shattered.
He presented many support letters to the court attesting to the man's remorse and good character, as well as a psychological report stating the "passive" and "insecure" young man was acting out to assert a sense of power and control and rid himself of "timid boundaries."
The man never intended to hurt anyone, Pinx said.
The Crown asked leMaistre to focus on enshrined Criminal Code principals of denunciation and deterrence, which apply because the man was charged as an adult.
Pinx spent considerable time arguing the unfairness of sending the man to jail when the co-accused youths saw none because they were sentenced under youth justice laws geared toward rehabilitation, not deterrence.
The age difference between the man and a more-involved youth co-accused was only nine months, their objectives were "identical" and circumstances very similar, argued Pinx.
"From a developmental perspective can we say (the accused is different than the 17-year-old)? Hardly," Pinx said.
The hearing was adjourned to Feb. 19.