After Junior Mika stomped on the head of a homeless person asleep outside a Sydney church, he took the man's only three possessions of value: his smokes, his lighter and his last $20.
He was sentenced to a minimum of three years in jail in the Sydney District Court on Friday.
Mika, who was also homeless at the time of the attack, stamped on the head of 63-year-old David Schmikli, at least five times as he slept on a park bench outside the Wayside Chapel in Potts Point on August 25, 2013.
The attack rendered Mr Schmikli unconscious, leaving him with facial fractures.
Mr Schmikli's possessions were found on Mika when he was arrested later that night.
He was found guilty of robbery and assault in July 2014.
While Judge Stephen Norrish said an aggravating factor in the case was that the victim was attacked as he slept, he also conceded that alcohol had played a role.
"There was no rhyme or reason for the attack," Norrish said as he handed down the sentence.
"There is no evidence the prisoner (Mika) is a psychopath. It was clear he was debilitated by alcohol."
The attack was the third time he had been charged with a violent offence in a one-month period.
Judge Norrish noted Mika's learning disability, with psychological reports classing him as borderline impaired, and the difficulties he has faced in finding a job.
He had been unemployed since 2008 before becoming homeless after his parents separated and moved back to New Zealand.
Mika will be eligible for parole on September 24, 2016.
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