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Canada's Prison System holds some of the most dangerous prisoners including serial killers, murderers and terrorists. Today we look at the top 28 worst of the worst ever held inside the Canadian Prison System.
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FunTranscript
00:00From the worst serial killers in Canada's history to some of the most dangerous terrorists
00:06in the country.
00:07Welcome to stories of the most dangerous people ever locked up in Canada's most feared prisons.
00:15If you enjoyed the video please drop a comment down below and let me know if I missed anybody.
00:19And don't forget to drop a like on it.
00:21Also we are now available for the hype feature so if you want to hype the video please go
00:25ahead it really will help.
00:28Number 28 Russell Williams
00:30A former colonel in the Royal Canadian Air Force, Williams was convicted of a series of crimes
00:35that began with breaking and entering and escalated to sexual assault and murder.
00:41His criminal activity started in 2007 when he began breaking into homes and stealing various
00:47items and taking pictures inside.
00:50Initially charged with 82 counts of breaking and entering, these crimes escalated to assault
00:56in September 2009 with two more home invasions near Tweed Ontario.
01:03For this he was charged with two counts of forcible confinement and two counts of assault.
01:09He was further charged with two counts of first degree murder on February 7th 2010 after being
01:15interrogated by an Ontario provincial police investigator.
01:20On October 21st 2010 Williams pleaded guilty to all charges.
01:25He was sentenced to two life sentences for the first degree murders, two ten year sentences
01:30for the assaults, two ten year sentences for forcible confinement and 82 one year sentences
01:37for the break ins.
01:38All sentences are to be served concurrently.
01:41He will serve a minimum of 25 years before he is eligible for parole.
01:45He is not eligible for early parole under the faint hope clause because he was convicted
01:50of multiple murders.
01:52Following his conviction he was stripped of his military commission, ranks and awards and
01:57his uniform and medals were destroyed.
02:00He is currently incarcerated at the Port Cartier Institution, a maximum security prison in
02:05Quebec.
02:06Number 27 Tara D'Souza Designated as Canada's youngest dangerous offender,
02:12D'Souza was formerly known as Adam Laboucan, was sentenced to an indefinite prison term for
02:19attacking a three month old infant in Quesnel, British Columbia.
02:24At just 15 years old, D'Souza has admitted to murdering a three year old boy when she was 11
02:30years old, a crime for which she was not charged as she was below the age of criminal
02:35responsibility at the time.
02:38D'Souza is currently incarcerated at the Fraser Valley Institution, a federal women's prison
02:45in British Columbia.
02:47She has had multiple parole applications denied, most recently in June 2024, as the parole
02:54board of Canada ruled that she presents an undue risk to society.
02:59Number 26 Elizabeth Wettlaufer
03:03Considered one of Canada's most prolific serial killers, this former nurse confessed
03:07to murdering eight elderly patients and attempting to harm six others in South Western Ontario
03:13between 2007 and 2016.
03:16Wettlaufer committed her crimes at various long-term care facilities and a private residence
03:21where she worked as a nurse.
03:23Her victims were vulnerable elderly patients.
03:26She used lethal doses of insulin, a drug that is difficult to detect in a deceased person,
03:33to kill her victims.
03:34She confessed to using insulin in all 14 cases, which included eight murders, four attempted
03:41murders and two aggravated assaults.
03:44A public enquiry into her crimes revealed she would likely not have been caught if she
03:49hadn't confessed to the murders.
03:52She had a history of disciplinary issues and had been fired from jobs for making medication
03:57errors and stealing opioids.
04:00Despite this, she was able to continue working in long-term care facilities.
04:04In 2017, Wettlaufer pleaded guilty to all charges.
04:08She was sentenced to life in prison with no chance of parole for 25 years.
04:13The judge gave her eight concurrent life sentences.
04:16This decision was influenced by her confession, which brought the crimes to light.
04:21She was initially incarcerated at the Vanier Centre for Women in Milton, Ontario.
04:27Later she was moved to a secure psychiatric hospital in Montreal.
04:31Wettlaufer will be eligible to apply for parole in 2041, but the judge noted that it is unlikely
04:37she will ever be granted it.
04:40Number 25, Jacques Mesrine.
04:42A notorious French criminal, Jacques Mesrine, along with his girlfriend Jeanne Schneider,
04:49fled to Canada in 1968 to escape law enforcement in France, but eventually became a public enemy
04:56in Canada.
04:58Upon arriving in Quebec, Mesrine and Schneider were employed as a chauffeur and housekeeper
05:03for a millionaire, Georges Deslauriers.
05:07After being fired, they kidnapped Deslauriers and demanded a ransom of $200,000.
05:13They also befriended and later allegedly murdered a widow, whose body was found strangled.
05:20They were eventually acquitted of the murder charge.
05:23After a brief escape to the US and subsequent extradition, Mesrine was incarcerated in Canada.
05:29He escaped from a Canadian prison with his girlfriend in September 1969.
05:35Following his re-arrest and another sentencing, he pulled off a more significant escape in
05:40August 1972 from Saint Vincent de Paul prison with five other inmates.
05:46During this period on the run, he and his accomplice Jean-Paul Mercier robbed multiple banks, sometimes
05:53committing two in a single day.
05:56They were also responsible for the murders of two forest rangers.
05:59Mesrine was imprisoned in Quebec, but he gained notoriety for his repeated and audacious
06:05prison breaks.
06:06His first escape was with his girlfriend from a prison in Gaspé.
06:10His most famous Canadian escape was from the Saint Vincent de Paul penitentiary, where he
06:15and five other inmates, including Jean-Paul Mercier, cut through a wire fence to get out.
06:21He became a high-profile target for Canadian law enforcement after he and his accomplices
06:26returned to attack the prison they had just escaped from.
06:30Mesrine returned to France at the end of 1972, where his criminal career continued.
06:36Number 24, Valérie Fabricant.
06:40A former associate professor who was convicted of murdering four colleagues and wounding another
06:44at Concordia University in Montreal, Quebec, Fabricant's crimes were the culmination of
06:51years of erratic behaviour and disputes with his colleagues.
06:55He was an associate professor of mechanical engineering at Concordia University and had
06:59a history of making threats and displaying undesirable to intolerable behaviour.
07:06He was facing dismissal from his position when, on August 24, 1992, he carried three handguns
07:12into the Henry F. Hall building on campus and went on a shooting spree on the ninth floor.
07:19He killed four professors, Matthew Douglas, Michael Hogben, Aaron Jan Saber and Foivos Ziogas.
07:26He also wounded a staff secretary, Elizabeth Horwood.
07:29After the shooting he took two people hostage, called 911 and demanded to speak to a TV news
07:35station to explain that the university had driven him to commit the murders.
07:41He was eventually disarmed and arrested by one of the hostages before police arrived.
07:46Fabricant was charged with four counts of murder.
07:50His trial was a long and difficult process during which he fired ten lawyers and chose to represent
07:56himself.
07:57He was described as being severely paranoid and hostile and was held in contempt of court
08:03six times.
08:04The jury found him guilty of all four counts of first degree murder.
08:09He was sentenced to life in prison and is incarcerated at the Arkham Bolt Institution
08:15in Quebec.
08:16From prison he has continued to be a vexatious litigant, filing numerous lawsuits against
08:21the courts and his former colleagues.
08:24In 2000, Canadian courts declared him a vexatious litigant, which limits his ability to file legal
08:31actions.
08:32Despite being in prison, Fabricant has also continued to publish scientific papers on theoretical
08:38topics and has been denied parole on multiple occasions.
08:43Number 23, Leopold Dion Dion had a lengthy criminal history that began when he was 17.
08:50In 1940, he was sentenced to life in prison for raping a 33-year-old woman, but he was paroled
08:57in 1956.
08:59His parole was revoked, but he was released again in 1962.
09:05In 1963, Dion committed a series of crimes against boys killing four.
09:10He would lure his victims, who were between 8 and 13 years old, by posing as a photographer
09:17with a camera that had no film.
09:20He confessed to killing four people, Guy Locarnock, Alain Carrier, Michel Morel and Pierre Marquis.
09:28He led investigators to the location where he had buried their bodies.
09:33Dion was arrested the day after his last murder.
09:35Another boy he had approached managed to get away and provided a description of him to
09:40the police.
09:41He was charged with four murders, but was convicted of only one, the murder of Pierre Marquis.
09:47On April 10, 1964, a judge sentenced him to death by hanging.
09:52His sentence was later commuted to life in prison.
09:55He was incarcerated at the Archon-Balt institution in Quebec, where he died on November 17, 1972,
10:02after being stabbed to death by a fellow inmate.
10:05Number 22, Carla Homolka.
10:08Another dangerous serial killer, Homolka was convicted of being involved in the murders
10:13of at least three minors in the early 1990s.
10:17Along with her husband, Paul Bernardo, Homolka helped to murder her 15-year-old sister Tammy
10:23Homolka, 14-year-old Leslie Mahaffey and 15-year-old Kristen French.
10:28The public outcry was intense because Homolka struck a controversial plea bargain with prosecutors.
10:35In exchange for her testimony against Bernardo, she pleaded guilty to two counts of manslaughter
10:41and received a 12-year sentence.
10:44This deal was made before police discovered videotapes of the crimes, which showed Homolka
10:49was a willing and active participant, not an unwilling accomplice as she had claimed.
10:55The plea deal became known as the deal with the devil.
10:58Homolka served her full 12-year sentence.
11:02She was initially held at a prison for women in Ontario before being transferred to the Joliet
11:07Institution in Quebec.
11:08She was denied early release by the National Parole Board, which stated she was still a
11:13risk to society.
11:15She was released from prison on July 4, 2005.
11:19Upon her release, a Quebec judge imposed strict conditions on her freedom, as there were concerns
11:26she still posed a threat.
11:28These conditions included curfews and restrictions on her contact with certain people.
11:34After her release, Homolka has reportedly lived under different names.
11:38She briefly moved to a Caribbean island, but has since returned to Quebec, where she has been
11:43reported to be living a quiet life with a husband and children.
11:48Number 21, Maurice Boucher.
11:50A Canadian gangster and a former leader of the Hells Angels Quebec Nomads chapter, Boucher
11:57was a central figure in the Quebec Biker Wars, a violent conflict that left more than 160
12:03people dead between 1994 and 2002.
12:08Boucher had a criminal history that included armed robbery and rape.
12:13His most notorious crimes, however, were committed during the Biker Wars.
12:17In an effort to destabilise the Quebec justice system, he ordered the murders of two prison
12:22guards, Diane Levine and Pierre Rondeau.
12:26Levine was murdered on June 26, 1997 and Rondeau was killed a few months later.
12:33Boucher was also convicted of the attempted murder of a third prison guard, Robert Corriveau.
12:39While in prison, Boucher continued his criminal activities.
12:43In 2015, he was arrested and charged with conspiring to assassinate a rival, Reynald Desjardins.
12:50He pleaded guilty to this charge in 2018 and received an additional ten-year prison sentence,
12:56which was to be served concurrently with his existing life sentence.
13:01Boucher was arrested in 1997. After a first trial in 1998 resulted in an acquittal, he
13:07was arrested again in 2000 and convicted in 2002. He was sentenced to life in prison with
13:14no possibility of parole for at least 25 years for the two counts of first-degree murder.
13:20He was incarcerated at the Saint-Anne-des-Plenes Penitentiary, a maximum security prison in Quebec,
13:26and died in prison on July 10, 2022 at the age of 69 after battling throat cancer for seven years.
13:3520. Luca Magnotta
13:37Convicted of crimes related to the 2012 killing of a 33-year-old Concordia University student, Jun Lin, in Montreal,
13:46Magnotta was also convicted of criminally harassing the Prime Minister and other members of Parliament.
13:52Magnotta had pleaded not guilty to the charges, admitting to the acts but claiming he was not criminally responsible
13:58by reason of insanity, arguing he was schizophrenic. However, the jury convicted him on all counts.
14:05In addition to these crimes, prior context mentions that Magnotta was previously sought
14:10by animal rights groups for uploading videos of himself hurting animals.
14:14He was also convicted in 2005 of one count of impersonation and three counts of fraud,
14:20to which he pleaded guilty and received a nine-month conditional sentence with 12 months of probation.
14:27Magnotta was sentenced to life imprisonment for the murder conviction,
14:31with no chance of parole for 25 years. He was also given the maximum sentences for the other four charges,
14:38totaling 19 years to be served concurrently and is serving an indeterminate life sentence.
14:44He will be eligible for day parole in June 2034 and for full parole in June 2037. However,
14:53eligibility dates do not guarantee an offender will be released.
14:57Magnotta was initially held in a maximum security institution in Quebec. In 2022, he was transferred to a
15:05medium security prison and Correctional Service Canada confirmed he met the criteria for this transfer.
15:12Number 19, Sharif Abdul Halim. Initially arrested as part of the 2006 Toronto terrorism arrests,
15:20Abdul Halim was alleged to have plotted bombing attacks against targets in southern Ontario.
15:26His targets specifically included the Toronto Stock Exchange, a Canadian security intelligence service
15:33building and a military base. The bombings were allegedly intended to be truck bombings and were
15:39planned to take place on three consecutive days to teach the world to be aware of that date forever.
15:46Court records indicate he played a critical part in the terrorist group, which included trying to
15:52purchase ammonium nitrate fertiliser for the bombs and contributing suggestions about the plan,
15:59such as spreading out the timing of the attack to increase the terror factor. He allegedly transferred
16:05two thousand dollars to an individual who was a police mole as a down payment for the fertiliser.
16:12A witness testified that Abdul Halim changed his mind and became excited by the prospect of profiting
16:18financially from an attack on the stock exchange. On January 21, 2010, Abdul Halim was found guilty
16:27and sentenced to life imprisonment for his role in the terrorist plot, plus one day in jail for
16:33participating in a terrorist group in addition to the time already served. After spending 14 years in
16:40a Quebec prison and receiving de-radicalisation counselling, Abdul Halim was released to a Montreal
16:47halfway house on day parole in January 2021. Number 18, Roche Theriot. Canadian cult leader and
16:56convicted murderer Theriot committed numerous acts of violence and abuse against members of his Ant Hill
17:03Kids cult. Theriot was involved in a wide range of horrific crimes against his followers and was
17:09convicted of second-degree murder for the death of cult member Solange Boilard in 1993. He was
17:17sentenced to a 12-year jail term for a brutal assault on cult member Gabriel Lavallee and was also
17:24charged with unlawfully causing bodily harm and three counts of aggravated assault. In 1993, Theriot pleaded
17:33guilty to second-degree murder and was sentenced to life imprisonment with no eligibility for parole for 10 years.
17:41He was transferred to Dorchester Penitentiary in New Brunswick, a medium security prison in 2000 and was
17:50denied parole in 2002. Roche Theriot died on February 26, 2011 at the age of 63 while incarcerated at
18:01Dorchester Penitentiary. His death was the result of an altercation with his cellmate, Matthew Gerard McDonald,
18:08who attacked him. McDonald pleaded guilty to the lesser charge of second-degree murder in Theriot's
18:14death and was sentenced to life without parole for 25 years because he was already serving a life
18:21sentence for a previous murder. 17. Hamed Shafia
18:26Hamed Shafia was convicted of four counts of first-degree murder along with his father,
18:31Mohammed Shafia and his mother, Touba Yahya, in connection with the deaths of four female
18:38family members in June 2009. The victims were Hamed Shafia's three sisters, Zainab, Sahar,
18:45Giti and his father's first wife in a polygamous marriage, Rona Amir Mohamed. The four bodies were
18:53found inside a car that was submerged in the Rideau Canal in Kingston, Ontario. Authorities theorised the car was
19:01intentionally pushed into the water. The Crown argued at trial that the murders were honour killings.
19:07They alleged the victims were killed because the three daughters had shamed the family by adopting
19:12western lifestyles, such as dating and wearing revealing clothing, which offended the defendant's
19:18twisted concept of honour. Rona Amir Mohamed, the first wife, had also sought a divorce and supported the
19:27girls. The jury found Hamed Shafia, along with his parents, guilty on all four counts of first-degree
19:34murder on January 29th, 2012. Hamed Shafia initially told a private investigator that he was present at
19:41the lock station when the car went into the water and did not call for help, but he maintained the
19:46deaths were an accident caused by one of his sisters taking the car. Hamed Shafia was sentenced to life
19:52in prison with no chance of parole for 25 years. This automatic sentence is given for first-degree
19:59murder verdicts in Canada. Hamed Shafia appealed his conviction and sentence arguing that new evidence
20:05indicated he was 17 years old at the time of the offences, not 18 as originally thought. His appeal to
20:12adduce this fresh evidence and his subsequent appeal from conviction and sentence were dismissed by
20:19the Court of Appeal for Ontario in November 2016. Number 16, Mark Smich. Smich had a criminal record
20:28involving petty offences such such as drug possession, driving impaired mischief, failure to appear and
20:35breach of conditions. Convicted of the first-degree murder of Tim Bosmer, a man who disappeared after
20:42going on a test drive of a truck he was selling, Smich was sent down on June 17, 2016 after Bosmer's body
20:51was found burned in an animal incinerator. Smich was also convicted of the first-degree murder of
20:57Laura Babcock, whose remains were never recovered and this conviction was delivered in December 2017.
21:05For each first-degree murder conviction, Smich received a sentence of life imprisonment,
21:11meaning he will need to serve a minimum of 50 years before he would be eligible for parole.
21:17A 2022 ruling by the Supreme Court of Canada found that consecutive parole ineligibility periods for
21:23multiple murders were unconstitutional. As a result, Smich's 50-year parole ineligibility period
21:32was reduced to no more than 25 years of parole ineligibility.
21:3715. Dellen Millard Another convicted murderer and
21:41accomplice of Mark Smich, Millard was convicted alongside him for the murders of Tim Bosmer and
21:46Laura Babcock, but was also convicted individually of the first-degree murder of his father, Wayne Millard.
21:53Millard was found guilty of assault causing bodily harm in March 2023 in connection with a stabbing of a
22:00fellow inmate at Millhaven Institution in July 2021. Millard is serving a life sentence for each of his
22:07three first-degree murder convictions and initially received a 75-year sentence, reduced to 25 years
22:15after a 2022 Supreme Court of Canada ruling. For the 2021 prison stabbing, Millard was sentenced to one
22:24year of imprisonment for the assault causing bodily harm conviction. This sentence is to be served
22:30concurrently with his prior murder sentences. Millard lost all three of his murder conviction appeals in 2023.
22:3814. Bruce MacArthur A self-employed landscaper, MacArthur was responsible for the deaths of eight men
22:46that became one of the most sensational crimes in Canadian history. He also posed and photographed
22:52some of his victims and kept personal items belonging to them with many of the bodies found inside his home.
23:00In addition to the murder convictions, MacArthur had a previous criminal history with a 2003 guilty conviction
23:07for assault with a weapon and assault causing bodily harm for an attack on a man in 2001.
23:14He pleaded guilty to all eight counts of first-degree murder on January 29th, 2019,
23:21thereby avoiding a lengthy and graphic trial. The judge ordered that MacArthur have no eligibility for
23:28parole for 25 years, meaning he would be 91 years old before he could apply for parole. The judge cited
23:36MacArthur's age and his guilty plea as factors in the decision to impose concurrent rather than
23:44consecutive periods of parole ineligibility. MacArthur's criminal status is incarcerated. He was
23:51detained at the Toronto South Detention Centre and, as of November 5th 2018, remained held there.
23:5913. Peter Demeter
24:02Hungarian-born Canadian former real estate developer Demeter was convicted in 1974 for arranging the
24:09murder of his wife, Christine Demeter, who was bludgeoned to death in the garage of their Mississauga, Ontario,
24:16home on July 18th 1973. The motive was believed to be collecting a $1 million Canadian dollar insurance policy.
24:25Demeter was sentenced to life imprisonment. The trial was the longest in Canadian history at that time.
24:32While serving his sentence and living in a convict's halfway house in 1983, Demeter was charged and
24:38later convicted in July 1985 of trying to arrange the kidnapping and murder of the son of his cousin,
24:45who was managing his financial affairs and taking care of his daughter. In 1983 he was also charged with
24:52arson in connection with a fire at the family home in Mississauga and, in 1988, Demeter was charged with
25:01planning to kidnap and murder the daughter of his lawyer. Demeter has been serving his term at the
25:07Medium Security Bath Institute in Bath, Ontario. While in prison, he has suffered a stroke and a heart
25:14attack and has had chemotherapy for three diagnoses of cancer. It was reported in March 2019 that
25:22Demeter had applied for parole, but the parole board denied to release him from prison. He said
25:28in a May 2006 CBC interview that he will be in prison for the rest of his life.
25:34Number 12. Barry McKenzie. He was convicted of theft and sent to the Guelph Reformatory.
25:39In his early criminal career, McKenzie was arrested for armed robbery in 1968 but escaped from the
25:46Halton County Jail by knocking out a policeman. Recaptured within half an hour, he was later
25:52sentenced to eight years in prison for armed robbery, escaping lawful custody and assaulting a
25:59police officer, a sentence he served at Kingston Penitentiary. He was described by a prisoner writer
26:05as one of the three toughest prisoners and a natural leader at the institution, being a key figure in the
26:12four-day riot at the prison that began on April 14, 1971. He was assigned to an inmate police force to
26:21keep order and protected undesirable prisoners from other inmates and aided a child molester,
26:29Brian Ensor, by forcing him into a cell for protection when other prisoners tried to kill him.
26:36To stop a potential massacre of the undesirables by other inmates on the night of April 17 to 18, 1971,
26:45McKenzie made the decision to release the hostages early on the morning of April 18, 1971, which helped
26:54bring the riot to an end. Number 11. Billy Knight. Known as the leader of the 1971 Kingston Penitentiary
27:01Riot, Knight's criminal record was lengthy, starting in his youth that included crimes of shoplifting
27:07and juvenile incarceration. After his release at age 15, he stole an automobile and was sent to the
27:15Guelph Reformatory for a year. He was a petty criminal, working mostly as a thief. In 1966,
27:22he was convicted of theft after breaking into a Salvation Army store and was sentenced to three
27:28years in prison. During the trial, he attempted to escape from the courthouse. While on parole in 1969,
27:35he smashed a store window to steal cigarettes. His parole was revoked and he was sentenced to another
27:42three years in prison. Knight was later convicted of these charges after escaping from a hospital where
27:48he was being treated for frostbite, though he was captured shortly after. He was sentenced to seven
27:54years in prison at Kingston Penitentiary. Knight was an inmate at Kingston Penitentiary. He served
27:59as the prison barber, which allowed him to know all of the inmates, as prison rules required them to
28:06have short hair and no facial hair. He was described as a well-liked mouthy type who was a natural leader
28:13among the inmates and a strong advocate for exposing prison conditions. He was also writing an autobiography,
28:21an expose of prison life called The Walking Dead. Sometime in March 1971, Knight began planning an
28:29uprising to protest conditions at the penitentiary and, oh the evening of April 14, 1971, Knight and
28:38six followers overpowered six guards. The riot, which was not an attempt to escape, resulted in
28:45trashing the place, the holding of six guards as hostages and the death of two inmates. During
28:52negotiations with a citizens committee, Knight made demands that a lawyer involved considered absurd.
28:58Another inmate eventually told Knight to dummy up, as other prisoners were getting tired of his
29:03bullshit and favoured surrender. Number 10, Omar Khada. Captured in Afghanistan on July 27, 2002,
29:12at the age of 15 following a firefight, this Canadian citizen was severely wounded during the incident,
29:19which resulted in the death of US Army Sergeant First Class Christopher Speer and injuries to other
29:26soldiers. The United States accused Khada of five charges of war crimes under the Military
29:32Commissions Act of 2006, including murder in violation of the laws of war, attempted murder in
29:40violation of the laws of war, conspiracy to commit terrorism, providing material support for terrorism
29:48and spying. After eight years of detention, Khada pleaded guilty in October 2010 to the five charges
29:57before a US military commission. He was sentenced to eight additional years of confinement under the
30:03terms of a plea agreement. Khada later retracted his guilty plea, claiming it was coerced to secure his
30:09return to Canada, but was the first person since World War II to be prosecuted in a military
30:16commission for war crimes, committed while still a minor. Khada was initially detained at the US air
30:23base in Bagram, Afghanistan, and then transferred to the US naval base in Guantanamo Bay, Cuba, in November
30:322002, where he was held for 10 years. Khada was transferred to Canada in September 2012 to serve the
30:40remainder of his sentence in Canadian custody, being held at Millhaven Institution, Edmonton Institution,
30:47and Bowdoin Institution. Number nine, Harvey Andres. A former member of the Grim Reapers motorcycle gang,
30:55Harvey Andres, was twice convicted for murder in 1981 and again in 2001, while also convicted of five
31:04counts of rape and a conviction for arson. He is notable for having two successful escapes from the
31:11Edmonton Institution, a maximum security federal institution in Alberta, once on March 12, 1981,
31:19and secondly on March 13, 1982. He was recaptured on April 19, 1981, after being wounded during a shootout
31:29with Calgary police and RCMP officers, in which an RCMP officer was also shot. After the second escape,
31:38he was recaptured after a similar shootout in Saskatoon, which left him wounded and during which
31:45a Saskatoon police officer was struck in the abdomen and arm. In the mid-1990s, he was the subject of an
31:52application for judicial review of his parole ineligibility period. This included a parole eligibility
31:59report by the Correctional Service of Canada, which contained psychological reports about his risk for
32:06general recidivism, with one report classifying him as a high risk. Number eight, Alan Legere. Known as the
32:14monster of the Miramichi, this Canadian serial killer has convictions that include murder,
32:20arson and rape, with crimes spanning from June 21, 1986 to November 24, 1989. A total of seven victims,
32:31two of whom survived included John Glenn Denning, Annie Flamme, sisters Linda and Donna Dorney, and father
32:39James Smith. Legere was apprehended on November 24, 1989 after a failed carjacking that ended outside
32:47Rogersville, where police arrested him in the cab of a tractor trailer. In August 1990, Legere was
32:54sentenced to an additional nine years for charges related to his escape. His trial for the four
33:00murders committed while he was at large began in 1991, and notably featured one of the first Canadian
33:06uses of DNA profiling to secure a conviction. In November 1991, a jury convicted him of four counts
33:14of first-degree murder, and he has since spent time in the special handling unit of Saint-Anne-de-Plaine,
33:21Quebec, and the Edmonton Institution in Alberta, where he remains currently imprisoned. Legere became
33:29eligible to apply for day parole in November 2012 and full parole in November 2015. In August 2020,
33:39he applied for day parole, but the Parole Board of Canada has denied his release.
33:46Number seven, Marie-Anne Hood. Marie-Anne Hood is historically known in Quebec for her role in the
33:54infamous child abuse and murder case of her stepdaughter Aurore Gagnon, often called Aurore the child
34:02martyr. The case, which took place in the early 1920s, became a major cultural sensation in Quebec,
34:10with the abuse reported to have begun in the summer of 1919, when Aurore returned to the family home.
34:18Marie-Anne Hood was arrested shortly after Aurore's funeral in February 1920, and Hoda's trial for
34:26murder began on April 13, 1920, lasting just eight days. Her defence team attempted a plea of not guilty
34:36by reason of insanity, citing the fact that she was pregnant at the time. However, this plea was largely
34:45unsuccessful. On April 21, 1920, Marie-Anne Hood was found guilty of murder by the jury, and was
34:53immediately sentenced to death by hanging, scheduled for October 1, 1920. Aurore's father,
35:01Telesphore Gagnon, was tried separately. He was convicted of the lesser charge of manslaughter and
35:08sentenced to life imprisonment, but was released after only five years for good conduct. Her death
35:14sentence was commuted to life imprisonment on September 29, 1920, just two days before the
35:21scheduled execution. This commutation was partially due to a reformist movement in favour of abolishing
35:28the death penalty. The case remains one of the most famous and culturally significant criminal cases
35:33in Quebec history, which cemented Marie-Anne Hood's reputation as the quintessential wicked stepmother.
35:42Number six, Wayne Bowden. Active between 1969 and 1971, this Canadian serial killer and rapist became
35:51infamous under the nickname The Vampire Rapist, or Strangler Bill. Bowden killed four women in total,
35:59three in Montreal, Quebec, and one in Calgary, Alberta, with victims including Shirley Audette, Marielle
36:07Archambault, John Way, and Elizabeth-Anne Porteous. Bowden was apprehended in Calgary in May 1971,
36:16after police linked him to the murder of Elizabeth-Anne Porteous. A broken cufflink found at the scene,
36:23and his distinctive blue Mercedes-Benz with a unique decal helped lead police to him. His trial for the murder
36:31of Elizabeth Porteous marked a historic moment, as it was the first murder conviction in North America,
36:38based on forensic odontological evidence. After being convicted in Calgary, Bowden was extradited to
36:45Montreal, where he confessed to three of the city's murders. He received a total of four life sentences
36:52for four counts of non-capital murder. Bowden began serving his sentence at the Kingston Penitentiary in
36:58Kingston, Ontario in 1972. Five years into his life sentence, Bowden managed to escape while on a day
37:05passed from a minimum security prison farm in Laval. During lunch at a downtown Montreal restaurant with
37:12his social worker, he excused himself to use the washroom and escaped through the bathroom window.
37:17He was later re-apprehended. Bowden died from skin cancer at Kingston General Hospital on March 27, 2006.
37:25Number five, Clifford Olsen. Clifford Olsen's criminal history spans decades,
37:30culminating in a string of murders in the early 1980s, followed by his subsequent incarceration.
37:37Olsen had an extensive criminal history before the murders, with over 90 convictions. His criminal
37:43career began by age 17, when he was convicted of breaking and entering and theft in July 1957,
37:51a crime he received nine months for. For the next 25 years before his last arrest,
37:57he was rarely out of prison for more than a few months. His convictions were mainly for burglary,
38:03fraud and theft. The murder spree began in November 1980, shortly after his release from jail
38:09on September 7, 1980, and lasted for about nine months in the metro Vancouver area of British Columbia.
38:17A total of 11 people met their end at the hands of Olsen, including Christine Weller,
38:23Colleen Marion Danio, Darren Todd Johnsrud, Sandra Lynn Wolfsteiner, Ada Anita Court, and Simon Partington.
38:32Other victims included Judy Cosmer, Raymond King II, Sigrun Arnd, Terry Lynn Carson, and Louise Chartrand,
38:41before Olsen was arrested on August 12, 1981. While in custody, he struck a highly controversial
38:49cash-for-bodies deal with the police and the Crown. He agreed to confess to the 11 murders
38:54and reveal the locations of the bodies of those not yet found. In return, a total of $100,000 was paid,
39:02into a trust for his wife and infant son, and he later pleaded guilty to 11 counts of first-degree
39:10murder, becoming one of Canada's worst serial killers. In January 1982, Olsen pleaded guilty to
39:1811 counts of murder, and was sentenced to 11 concurrent life sentences, with no eligibility for
39:24parole for 25 years. The trial judge recommended he should never be granted parole. He was initially
39:31sent to Kingston Penitentiary's Protective Custody Unit, and later served his time in the Special
39:37Handling Unit in Saint-Anne-des-Plaines, Quebec. Clifford Olsen died on September 30th, 2011,
39:45at the age of 71, in a hospital in Laval, Quebec, while in prison custody from terminal cancer.
39:53Number 4, Ty Conn. Conn's criminal history began early. He developed a habit of compulsive stealing
40:00during his time with his adoptive parents, starting with food and escalating to cars by his teens.
40:06From age 13 to his death at age 32, Conn was only legally at large for a total of 69 days, having spent
40:1418 of those 32 years in juvenile and adult prisons. In 1998, Conn was transferred to Kingston Penitentiary
40:23after he had acted as an informant at the Millhaven Institution, advising staff that fellow inmates
40:29were planning an escape. He was placed in protective custody. Conn escaped from Kingston Penitentiary on
40:36May 6th, 1999, one of the most famous escapes in the prison's history, being the only time in the
40:44last half century that a person successfully went over the wall of the highly secure prison. He was
40:51the first inmate to escape in more than 40 years, and used a ladder and a homemade grappling hook to
40:57scale the wall. He also used cayenne pepper to prevent dogs from following his scent. Conn was found
41:04in a Toronto apartment building approximately two weeks after his escape and died from a self-inflicted
41:10gunshot wound from a stolen shotgun. While some accounts state he committed suicide rather than
41:16be captured, other theories suggest he may have accidentally discharged the shotgun while speaking
41:21on the telephone to Teresa Burke, a CBC producer. 3. Michael Rafferty
41:27Rafferty and his accomplice Terry Lynn McClintick were both convicted of first-degree murder in the case of
41:33eight-year-old Victoria Stafford, who was murdered on April 8th, 2009. McClintick initially told police
41:40that Rafferty killed the girl, but later testified at his trial that she'd delivered the fatal blows.
41:46During the trial, evidence that was not shown to the jury due to a faulty search warrant included what
41:53was found on Rafferty's laptop. Rafferty was sentenced in 2012 to an automatic life term with no chance of
42:00parole for 25 years for first-degree murder. He also received concurrent 10-year sentences for kidnapping
42:08and sexual assault causing bodily harm. He has been in custody since May 2009 and won't be able to apply
42:15for parole until May 19th, 2034, yet he appealed his conviction arguing that he was at most an accessory
42:25after the fact to murder and that the judge made errors. The Court of Appeal for Ontario dismissed his
42:32appeal on October 24th, 2016 and he was transferred from a maximum security prison to a medium security
42:41facility in March 2018. 2. Robert Picton
42:47Often referred to as the pig farmer killer, Picton's criminal activities spanned from 1978 to 2001 in
42:56British Columbia, Canada. He targeted vulnerable women, often sex workers and those struggling with
43:02substance abuse from Vancouver's downtown Eastside. Picton is believed to have murdered at least 26 women
43:10and later confessed to an undercover police officer that he killed 49 women.
43:15The remains of many of the victims were discovered on his pig farm in Port Coquitlam and he was also
43:21charged with the attempted murder of a sex worker in 1997 whom he had stabbed multiple times, though this
43:29charge was later stayed. Picton was arrested in February 2002. He was eventually charged with 27 counts of
43:38first-degree murder and his trial in January 2006. In 2007, a jury found Picton not guilty of first-degree murder but guilty on six counts of second-degree murder.
43:52He was sentenced to life in prison with no possibility of parole for 25 years. Picton served his life sentence at a maximum security prison, Port Cartier Institution in Quebec, where he had been incarcerated since 2018.
44:06Picton died on May 31st, 2024, at the age of 74, following an assault by another inmate named Martin Charest, who attacked Picton with a broken broom handle stating he did it for the victims.
44:241. Paul Bernardo Often dubbed the Scarborough Rapist and, along with his ex-wife Carla Homolka, one of the Ken and Barbie killers, Bernardo was designated a dangerous offender, which usually results in an indeterminate sentence.
44:42Between 1986 and 1990, Bernardo committed a series of assaults in Scarborough, Ontario. He would later admit to the assaults of at least 14 women in southern Ontario, and at one point faced 53 charges.
44:56In December 1990, Bernardo and Carla Homolka drugged and attacked Carla's younger sister, Tammy Homolka. While she was unconscious, she later died due to an allergic reaction to the drugs.
45:10In June 1991, Bernardo kidnapped 14-year-old Leslie Mahaffey and, with Homolka, murdered her before he and Homolka kidnapped 15-year-old Kristen French from a church parking lot in 1992.
45:24Bernardo was found guilty on all nine counts on September 1st, 1995, and sentenced to life imprisonment with no parole for 25 years for the two murder charges.
45:37Bernardo began serving his life sentence on September 1st, 1995, and was initially admitted to Kingston Penitentiary for the first 28 years of his incarceration.
45:48He was transferred from Kingston Penitentiary to Milhaven Institution in September 2013, following the closure of Kingston Penitentiary.
45:57He spent about a decade at Milhaven. On May 29th, 2023, Bernardo was transferred from Milhaven Institution to La Macasa Institution in Quebec.
46:07The transfer was approved after he demonstrated an ability to integrate on his range in Milhaven.
46:13Bernardo has been classified as a conformist, meaning he has been the victim of attempted and actual assaults, but has not engaged in violence against other offenders or staff.
46:24However, records show he was the instigator in nine incidents over two decades, and contraband has been found in his cell three times.
46:34A 2014 risk assessment identified a high probability of risk for violence towards a partner and a moderate risk of violence towards others.
46:45He is still assessed as a high risk to public safety and retains his dangerous offender designation.
46:52He then
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