Predator Richard Rupert a four-decade con man

Richard Earl Rupert (above) is a remorseless, ruthless predator with no regard for the senior citizens he tricks and swindles. Unbelievably, Rupert has been doing it for nearly four decades, archived parole records reveal. Cancrime recently obtained six years worth of records (available after the jump) for the con man that police across Canada are still hunting. The records disclose his abysmal record of failures on early release from prison after five federal penitentiary terms and they show that he has duped prison and parole authorities in the past into believing that he has remorse for his victims and that he wants to go straight.

The documents above constitute the formal record of four separate parole decisions involving Rupert between 1998 and 2004

The documents show that Rupert has mocked his victims, who could number in the hundreds. He shows no sign of stopping his relentless crime spree.
“We have no question that he’s still active,” Det. Const. Michael Thomas, a Toronto Police officer who is hunting Rupert, said in an interview April 9.
Thomas said they were able to track Rupert to Ottawa, but after that the trail went cold.
Rupert, 54, often shows up at nursing homes masquerading as a long lost relative of a resident. He ingratiates himself, typically by spending hours in conversation, and eventually asks for cash to deal with a minor emergency like a car breakdown (more on his methods in this previous post).
In January this year, Toronto investigators issued a Canada-wide warrant for his arrest, alleging he has bilked at least 20 people, and perhaps dozens more, in cities across Ontario and as far west as Vancouver. Police also released video that shows him assaulting an 81-year-old North York woman he was trying to fleece.
Police have been stymied in efforts to find Rupert.
“He is truly a ghost,” Thomas said, noting that Rupert operates without credit cards, a drivers licence, vehicles or a cell phone – items that would leave a trail.
He travels by bus, often along the Trans-Canada Highway, staying in one city just long enough to victimize a few seniors.
“Sadly, they’re very, very easy targets,” said Thomas, who is still hopeful that a keen-eyed citizen or a victim will provide the tip that will reel in the elusive fraudster.
It’s feared Rupert has left behind a trail of mostly unknown victims in many cities, including Kingston, who are too embarrassed to come forward.
“He targets that one particular group who are very, very insecure and the last thing they want is to be seen as old fools,” Thomas said.
Rupert has been slippery even when he is supposedly under the watchful eye of the corrections and parole systems.
In 1998, just four days after he was granted day parole, a form of early prison release that allowed him to live at a halfway house, he bolted and was not recaptured for more than two and a half years, the parole documents reveal.
He immediately began preying on elderly victims.
He was granted release in 1998 after convincing the parole board that he was ready to turn his life around.
“At the hearing he projected as being sincere and committed to address his unresolved issues,” states a written record of the hearing. “He expresses remorse for his many victims and appears to be accepting responsibility for his offending.”
Authorities now know that Rupert simply returned to his “entrenched criminal lifestyle” nearly as soon as he passed out through the prison gate.
His release came despite acknowledgment by parole board members of Rupert’s “poor compliance rate in his prior conditional releases.”
“In the past he has not expressed any remorse for his actions and apparently laughed at how gullible his victims were,” the 1998 record also stated. “It should be noted that a majority of his victims were elderly during his extensive long term criminal behaviour.”
The last time the parole board reviewed Rupert’s case, in April 2004, it noted that he had “ongoing mental health issues” that required psychiatric intervention.
At the time, he was freed from prison on statutory release, a form of automatic early freedom. The parole board could not order him held behind bars, but it imposed special conditions, including requirements that he submit to psychiatric counselling and take medication.
The records note that he was taking “psychotropic medication.” He also has “significant cognitive deficits including short-term memory loss.”
Rupert’s last sentence, a six-year term for fraud and other property crimes, has since expired so he was not subject to supervision at the time last year when police issued the warrant for his arrest.
Rupert is white, five foot six inches tall, 140 to 160 pounds, with short, dirty blond-gray hair and a receding hairline.
He has a reddish complexion, with chiselled cheekbones, hazel eyes and is usually clean-shaven.
Anyone with information can call Toronto Police at 416-808-3200 or Crime Stoppers anonymously at 416-222-TIPS (8477), online at, or text TOR and your message to CRIMES (274637).

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