Top 15 Most Dangerous Scottish Prisoners

Some of Scotland’s most dangerous Scottish prisoners lie within the countries harshest prisons and some have even died within the penitentiary’s walls.

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15 – Tiffany Scott

Subject to an Order for Lifelong Restriction after admitting to stalking a 13-year-old girl by sending her letters while serving time in prison, Scott died in HMP Grampian during her sentence in 2024.

First convicted of attacking a nurse in Cheshire, England, in 2010, while trying to escape from a hospital, she was sentenced to 14 months in prison.

After making a transgender change from a man to a woman in 2016, Scott was told she would not be released until she was no longer considered to be an unmanageable risk to public safety.

After being sentenced to a further year in prison for attacking officers, she further attacked several officers in 2023, another two years in prison was added to the sentence.

Later in 2023, Scott made national headlines after successfully applying to be moved to a women’s prison, a move that was later blocked by the Scottish Prison Service.

New guidelines were subsequently introduced requiring transgender offenders convicted of violent offences against women to be housed in male prisons.

14 – Edward Cairney

Jailed in 2019 along with his partner Avril Jones for murdering vulnerable 19-year-old Margaret Fleming, Cairney died at HMP Edinburgh in 2023.

Sentenced to life, Cairney initially got away with the killing after Fleming was not noticed to have been missing for almost 17-years.

Cairney and Jones, her supposed carers at the time of her disappearance were later arrested in 2017 and found guilty of murder and perverting the course of justice.

They were handed life sentences with a minimum term of 14-years and the whereabouts of Fleming remains a mystery to this day.

The couple even claimed Flemings benefit money, totalling £182,000 while pretending she was still alive.

13 – Robert Bayne

In what became known as the Wishaw murder, 17-year old Zoe Nelson was attacked near a colliery spoil heap known locally as Monkey Hill.

Bayne, who was later found to be the killer, constructed a makeshift pyre to try and destroy the evidence of the crime.

After using new media for the first time in a murder investigation, it was revealed that his sister had withheld the identity of the killer for five days.

Bayne was found guilty of her murder and a second charge of attempting to defeat the ends of justice was also applied at trial.

He was handed a minimum term of twenty years, for the murder and six years, to be served concurrently, for the second charge after a psychiatric report deemed him sane.

12 – Isla Bryson

Similar to the Robert Bayne case, Isla Bryson is a 31-year-old Scottish transgender woman who was convicted of the rapes of two women before her gender transition took place.

Charged in 2019 and later transitioning in 2020, Bryson attempted to mix with local women at a college before being remanded to a women’s prison to await sentence.

Bryson’s six-day trial was held in January 2023 at the High Court of Justice in Glasgow and it was revealed that Bryson had stalked female partners online.

Found guilty on the 24th January 2023, Bryson was sentenced to eight years in a male prison after the court recorded the crimes having been committed by a man.

11 – Nicholas Rossi

One of the most famous prisoners to ever be held at Edinburgh Prison, Rossi went by a number of aliases, including that of Arthur Knight.

Rossi was wanted by authorities in Utah for an alleged rape that occurred in 2008, but had not only faked his own death but fled the United States and had been on the run for 12-years.

Unfortunately for Rossi, he ended up in hospital during the events of 2020 and was later identified by tattoo’s on his arm.

After many bail hearings, some of which were successful, a sheriff finally ruled that he could be extradited to the United States in August 2023.

Rossi was extradited on the 5th January 2024 and he is now being held at an unknown location while awaiting trial.

10 – William Beggs

Convicted of murdering teenager Barry Wallace in 1999, Beggs became known as the “Limbs in the Loch Killer”, after his victim was found in Loch Lamond.

Wallace was a supermarket worker who went missing after a staff Christmas party and the crime was described as one of Scotland’s most horrific at the time.

Convicted at the High Court in Edinburgh in 2001, it was later revealed that Beggs had been cleared of a similar murder on a technicality.

Beggs had also been the subject of an extradition order, having fled to Amsterdam while facing murder charges.

Having been convicted of murder and multiple charges of attacking other people, Beggs was handed a 20-year sentence in 2001, he has had every parole application denied since.

9 – John McHugh

Serving a life sentence for for the violent murder of waiter John Stewart, McHugh was sentenced to 45-years.

Once Scotland’s longest serving prisoner, McHugh described to police how he committed the crime for fun.

He was locked away inside a psychiatric hospital in Lanarkshire but later escaped, leading police on a manhunt after climbing through an open window.

He made the headlines in 2020 after claiming to have seen inmates beaten at HMP Perth while serving time there, a claim the Scottish Prison Service denies.

8 – Hugh Collins

Once branded as Scotland’s most dangerous prisoner, Collins had a reputation for shoplifting, burglary and violence.

After bumping into a known rival in a bar, a fight ensued, with Collin’s rival initially starting the altercation.

He was stabbed multiple times by Collins, who was later arrested, charged and found guilty at the High Court in Glasgow.

Sentenced to life imprisonment, Collins sentence was the culmination of 10 years of violent crime for which he had been in and out of prison on multiple occasions.

In the first three weeks of his life term, he had attacked three prison officers and was often kept in isolation and underground cells.

After spending some of his sentence in a straitjacket, he became known in the media as “Scotland’s most dangerous prisoner”, once enduring 14 months of solitary confinement.

He was released in 1993 and had since expressed shame over killing, while turning his life around.

He died in August 2021 at the age of 70.

7 – Steven Leisk

Out on licence for another attack, Leisk went on to attack nine-year-old Scott Simpson at a playpark in July 1997, fatally injuring the boy.

He was later caught, tried and found guilty of the crime, being sentenced to life with a minimum of 20-years.

Several attempts at parole have been made after he was automatically added to the application process.

His first appeal was denied and a second appeal was launched two years later, with that also turned down after serving 22-years.

Leisk will be up for parole every two years and the victims family are doing everything in their power to make sure the requests are denied.

6 – Robert Mone

On the 1st November 1967, Robert Mone went absent without leave from his army unit and after drinking for days and armed himself with a shotgun.

He attacked a needlework class at St John’s High School while wearing his uniform, killing one and holding the class and another teacher hostage for 90-minutes.

His motive was revealed to be revenge for expulsion from the school and he was later found to be insane and sent to a State Hospital in South Lanarkshire.

The story does not end there and, after escaping from the hospital, Mone and an accomplice killed again, this time three victims were added to the list.

They were once again caught after a high-speed police chase on the A74 near Carlisle and were sentenced with a recommendation that they never be released.

Mone led a rooftop protest over his conditions in HMP Perth in 1981 and had six months added to his sentence in 1995 for attacking a fellow prisoner.

Today, he is Scotland’s longest serving prisoner and has studied law and philosophy, while also transcribing books into Braille.

5 – Abdelbaset al-Megrahi

After being revealed as one of the main perpetrators of the bombing of Pan Am Flight 103 over Lockerbie, al-Megrahi was initially held under house arrest in Libya.

He was next designated as a United States fugitive from justice and added to the FBI’s ten most wanted list with a $4 million reward.

After a lengthy discussion, a trial for al-Megrahi was held at Camp Zeist in the Netherlands on 5 April 1999.

He was found guilty, and was sentenced to life imprisonment, with a recommendation that he should serve at least 20 years.

Megrahi spent almost 8-years in various Scottish prison’s, before he was released on compassionate grounds, having been diagnosed with advanced prostate cancer.

He died on the 20th May 2012 at his home in Tripoli.

4 – Peter Tobin

One of the most well-known serial killers in Scottish history, Tobin initially served 10 years in prison for the rape and indecent assault of two girls in 1993.

After being released in 2004, he attacked Angelika Kluk in Glasgow, sometime in 2006, a crime which he received 21-years for.

Other crimes that Tobin had committed began to come to light and the remains of two teenagers, who went missing in 1991, were subsequently found at his former home.

Diagnosed as a psychopath by a senior psychologist, Tobin was handed a whole life order in 2009 and will never be released.

Initially connected with the Bible John murders of the late-1960s, Tobin was ruled out of this investigation but has claimed as many as 48 victims.

3 – Peter Manuel

Nicknamed “the Beast of Birkenshaw” before his identity was known to the media, Manuel was born to Scottish parents in New York City and migrated back to Scotland in 1932.

He was later convicted of seven murders, all of them women, except for Peter and Michael Smart, who died in their Uddingston home in the early hours of 1 January 1958.

Many police officers suspected Manuel of committing the crimes, yet evidence was sketchy at best until he paid for drinks at a local bar using stolen bank notes from the Smart’s residence.

He confessed to the murders after his father was arrested, and a sensational trial followed at Glasgow High Court.

Representing himself at trial, he was unable to convince the jury of his innocence and was found guilty of all charges, except for one murder, that of Anne Kneilands.

On July 11th 1958, Manuel was hanged on the gallows with his last words reported to have been “Turn up the radio, and I’ll go quietly”.

2 – Dominic Devine

Known as the Beast of Ibrox, Devine was a British convicted sex offender and serial rapist that was sentenced to life imprisonment in 1987.

Only the third person in Scottish history to be sentenced to life imprisonment for rape, Devine attacked five women in the Ibrox area of Glasgow.

He was held in a number of prisons throughout the country, before arriving at HM Prison Shotts in 2009.

He was found to be exploiting the work release program to smuggle drugs into the prison after day-release sessions, with the investigation carried out by the Sunday Mail.

Returned to prison on further charges, it was reported that he had been released in 2017, yet this was untrue and he died at Scotland’s largest prison in 2023.

1 – James O’Rourke

Named as one of the 10 most dangerous prison inmates in the world, double killer O’Rourke recently admitted to murdering a fellow inmate in a brutal execution.

Convicted for murdering Neil Cairney in 1992, he was sentenced to a further six years for holding hostage a prison officer and a nurse for 19-hours.

He was given another 8-years in 2002 for abduction and then committed another attack in 2004, which brought another 4-year sentence.

In 2005 he stabbed a prison escort and a senior jail official at HMP Kilmarnock, resulting in a further 8-year sentence, and was handed another 9-year sentence in 2019 after attempting to murder another prisoner in the prison gym.

His second life-sentence came in July 2022 after admitting to killing fellow prisoner Dean Ramsey 18-months earlier, attending court with the worst criminal record ever seen.

Nicknamed “Porky” in prison, he has cemented himself at the top of the prison hierarchy with both inmates and prison officers living in fear of him.

At one point, he became so violent, that he was delivered his own menu into his cell, so that he could eat away from other prisoners.

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