He's just 25, already serving life in prison for murder along with a 10-year bit for a brutal aggravated assault that left a man in a virtual vegetative state.
So how do you sentence Jonathan Diego Young — at least in a way that's at all meaningful — for any lesser crimes he's committed at this point?
That's the difficult question a prosecutor, defence lawyer and a Manitoba judge grappled with today as Young appeared in court to learn his sanction for a June 2012 assault on an inmate at Stony Mountain Institution where he cut him with a nail wrapped in a cloth.
"There's not much you can do," prosecutor Keith Eyrikson told provincial court Judge Janice leMaistre.
"Frankly, I'll be long retired... before Jonathan Diego Young sees freedom again," defence lawyer Amanda Sansregret added.
Young was arrested in custody for the assault while awaiting trial for the October 2009 murder of Ryan Chartier, 21, in The Pas, a crime he's since pleaded guilty to. He was made ineligible to request a shot at parole for 16 years.
Chartier was shot to death inside an apartment block. Young was also convicted of attempted murder in that case for wounding a 21-year-old man.
The assault he was dealing with this morning involved an attack on an inmate inside an exercise yard.
At first, it appeared it could have been a consensual fight between the men. Young was charged after the victim suffered relatively superficial injuries from the makeshift weapon and had to be treated briefly in hospital.
The last time Young attacked an inmate, the results were extremely ugly.
He was one of several Indian Posse members housed at the Milner Ridge Correctional Centre who brutally assaulted a 33-year-old man after a door was accidentally unlocked by staff and the gangsters "surreptitiously" held it open until they could attack.
The group savagely attacked the victim because he'd earlier made a rude gesture towards them.
If there's any hope to be had for Young's future prospects, it's how he's been embracing his aboriginal culture in custody and making efforts to upgrade his education, Sansregret said.
He's also "rolled out" of the Indian Posse, meaning he's no longer with the gang but finds himself in danger from them because he left.
It's one of the reasons he serves his prison time locked in segregation 23 hours a day.
The second: Young is considered a maximum-security federal inmate but was recently moved back to Manitoba because his family is here. Stony Mountain is only classified as a medium-security prison until construction on a maximum-security section is complete, Sansregret said.
Young's upbringing had virtually all the hallmarks to predict future problems: Exposed to alcohol, abuse and trauma in a dysfunctional home, he found himself placed in foster care and then fell into gang life and criminal activity.
LeMaistre acknowledged his troubled upbringing, saying it was one "no one should have had to endure." That said, she suggested she was struggling with how to send him a meaningful message to denounce his latest violent outburst.
In the end, leMaistre endorsed a five-year prison term for the assault as jointly-recommended by Sansregret and Eyrikson, to be served concurrently to his other sentences.