Men who escaped from the Regina Correctional Centre on Sunday had gang connections, served prison time for violent crimes and were considered at high risk to violently reoffend, National Parole Board records say.
Police have warned the public that the five men who escaped Sunday and remain at large are dangerous.
Police have released few details, but documents CBC News obtained from the parole board indicate that two of the escapees, Daniel Richard Wolfe and Ryan John Agecoutay, have both served time in prison for violent crimes and have extensive connections with street gangs.
More than a decade ago, Wolfe broke into a home to collect on a gang debt and threatened to kill his victims with a sawed-off shotgun. He was convicted in March 1999 and received an eight-year prison sentence. The parole board said he showed no remorse.
Wolfe repeatedly breached parole by hanging out with gang members, at one point being caught wearing full gang regalia. He had also been extensively involved in gang activity while he was behind bars, the board said.
Wolfe, 32, is now charged with first-degree murder in connection with a violent home invasion last fall.
Agecoutay has also been to prison. Seven years ago, he was part of a group that broke into a home in the middle of the night. Agecoutay threatened to kill several people with a handgun, including a young child, parole board records said.
He was sentenced in 2001 to three years and 10 months for assault causing bodily harm and a variety of other offences. One of them was obstructing justice, after phoning a co-accused from behind bars and threatening to have him killed if he testified against him, a 2002 report said.
Unlike most prisoners, Agecoutay was not released after serving 2/3 of his sentence and remained behind bars until Feb. 10, 2005.
A parole board report from 2002 said Agecoutay was an active member of a street gang. It said he was the leader of a violent and destructive riot while in custody.
That document said he hears voices in his head, and silences them through drugs and violent behaviour. It said if released, Agecoutay would be an "unmanageable risk to cause an offence causing serious harm to another person."
At the time of the jailbreak on Sunday night, Agecoutay, 25, was awaiting trial for aggravated assault.
The other three people who escaped and remain at large include Preston Clarence Buffalocalf, 22, James Joseph Pewean, 25, and Cody Dillon Keenatch, 19.
The parole board records concern Agecoutay's and Wolfe's records in the federal prison system.
The issue of gangs in Saskatchewan's provincially run jails became a source of embarrassment for the government this week when Corrections Minister Darryl Hickie told reporters there was no gang problem in provincial facilities, then later reversed himself and said there was a problem.
On Thursday, news media obtained a faxed memo from the premier's office that said Hickie won't talk about the jailbreak anymore while the case is being investigated.