Shocking timeline reveals how dangerous Sheffield rapist keeps getting second chances
A dangerous rapist from Sheffield is now serving three life sentences after continually using his chances at freedom to attack women.
“I’m sorry you dedicated your entire life to violence against women,” Neil Trennan’s latest victim said as she bravely confronted one of Sheffield’s most vile criminals at court on Tuesday, February 24.
The 61-year-old convicted rapist is now serving three life sentences following a lifetime of violence and sexual offences against women.
In 1990, he shocked the city when he committed a horrifying attack against a 30-year-old woman in her home.
Trennan - who lived in Wincobank at the time - hit her with a dumbbell, knocking her unconscious, before raping her and continuing to beat her.
Detective Inspector Tony Martin told The Star while investigations were ongoing: “I have never known anything like this incident.
“The injuries were inflicted in a vicious and mindless manner. Some sort of blunt instrument was used on her and there were 11 separate head and facial injuries.”
It resulted in Trennan’s first life sentence when he was only 25, with The Star at the time branding him ‘one of Britain’s most dangerous men’ and a Sheffield judge calling him a ‘serious threat to women’.
Yet, 12 years later, on June 28, 2002, he was granted supervised leave in Norwich city centre.
When his assigned prison guard turned his back, Trennan ran, finding himself at a local college.
In the ladies toilets, he beat a woman with a brick and was sentenced to life imprisonment for a second time.
PC Kate Thacker, who was involved in the investigation, said after the sentencing: “Trennan is a dangerous man, a repeat offender and a danger to women.
“We are all pleased with the result of the trial and his sentence.”
A judge at the time described Trennan as a risk to the public, with a barrister quoted in The Star adding: “Those responsible for the release of Trennan in the future will look to what he was doing on June 28 this year and will inevitably think here is a man that we can no longer be sure is going to be safe.”
At the time, The Star reached out to the Home Office who according to contemporary reports said that day release is vital for rehabilitation, but may review their policies depending on the results of an investigation.
A spokesperson was quoted as saying: “We carry out many thousands of these visits, and although this is a terrible case, it is extremely rare.”
Their comment is eerily similar to the latest remarks from the Ministry of Justice (MOJ), after Trennan was once again allowed leave from prison which he used as an opportunity to attack a Sheffield university student in her home.
In July 2025, he was granted unsupervised leave from HMP North Sea Camp, an open prison in Boston, Lincolnshire, and went on the run for three days, during which time he attempted to assault the 19-year-old woman with a knife in Nether Edge.
“These were horrendous crimes and our thoughts remain with all the victims affected. Neil Trennan has rightly received the full weight of the law for his actions,” an MOJ spokesperson said in a statement on February 26.
“We want to fully understand what happened in this case, including whether any processes or policies need to be strengthened.”
In their response to The Star, they included details talking about the importance of Release on Temporary Licence (ROTL) - a type of unsupervised day release with conditions imposed - for rehabilitation, adding that 99 per cent of such releases go according to plan.
Much like his predecessors, The Recorder of Sheffield, Judge Jeremy Richardson KC, described Trennan as a ‘substantial threat to women’ when imposing his third life sentence on February 25.
“This is an appalling case of history repeating itself - that must never happen again,” Judge Richardson continued.
“No woman is safe whilst ever you remain at large.
“I make it plain that although I am required by law to determine a minimum term you must serve, it is my view that I cannot envisage a situation arising where it is ever safe to consider you being released.
“This is one of those fortunately rare cases where it is highly likely you will spend the rest of your life in prison in circumstances of considerable security and you will die in custody”