An ‘obsessive’ headteacher who bombarded a trainee teacher with messages as he tried to start a relationship with her was jailed for 20 weeks today.
Gregory Hill, 49, harassed Chloe Regester, 25, for nearly a year, contacting her through Facebook and WhatsApp and even ordering her to go with him and pupils to Sandringham after the late Queen died.
When he discovered the object of his attention was gay, he made withering remarks about her partner and belittled her dress sense, saying she had ‘lesbian shoes’.
When Hill was arrested in the car park of his school he spent 30 minutes lying on the ground and wrestling with officers, who caught the ‘bizarre’ scene on bodyworn cameras.
Sentencing the disgraced educator, District Judge Christopher Williams said he had a ‘chilling ignorance’ of the power he held over staff at Howard Junior School in King’s Lynn, Norfolk, which had led to his ‘spectacular fall from grace’.
Gregory Hill, 49, (pictured outside Norwich Magistrates Court)harassed Chloe Regester, 25, for nearly a year, contacting her through Facebook and WhatsApp and even ordering her to go with him and pupils to Sandringham after the late Queen died
When Hill found out Ms Regester was a lesbian, he made withering remarks about her partner and belittled her dress sense, saying she had ‘lesbian shoes’
When Hill was arrested in the car park of his school he spent 30 minutes lying on the ground and wrestling with officers, who caught the ‘bizarre’ scene on bodyworn cameras
He added: ‘Even now, you fail to realise how wrong your behaviour was.
‘You abused the power you held, especially over young members of staff at the school. You are an obsessive individual.’
Hill – who won a local award for Inspirational Teacher of the Year in 2022 – had denied harassment and resisting arrest but was convicted following a trial at Norwich Magistrates Court last month.
The unwanted romantic campaign began in March that year, just a few months after Ms Regester had left Durham University with a first-class degree in primary education.
Messages she received included one that said: ‘This is confidential but I have fallen in love with you. It’s hard for me but I will always be fun, kind and supportive.’
When he told her he loved her on another occasion, desperate Ms Regester wrote back: ‘I’m sorry Greg. I have never said that I have feelings for you. This has to stop.’
There were 13 occasions when Hill, who was suspended after his arrest and has since lost his job at the school, should have known his behaviour towards a junior member amounted to harassment, prosecutor Monali Raleraskar told the trial.
Ms Regester, who quit her job as the school’s leader for art and design and technology following her ordeal, struggled to control her emotions as she gave evidence via videolink.
Ms Regester said Hill ‘requested her personal attendance’ to accompany him to Sandringham last September following the death of the Queen
who quit her job as the school’s leader for art and design and technology following her ordeal, struggled to control her emotions as she gave evidence via videolink
She said: ‘I was scared. I didn’t know what he was capable of or what he might do.’
She added he made it clear her ongoing training – which had to be signed off by him – was used as leverage against her. ‘He held it over me,’ she said.
The defendant, of Fakenham, claimed Ms Regester had ‘blown hot and cold with him and said she and another teacher who gave evidence against him had ‘colluded to manipulate the situation to make money’.
In a victim impact statement read out at today’s sentencing, Ms Regester described the messages she received as a ‘constant drain’ on her mentally and physically.
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‘He was always hounding me with messages and emails late at night,’ she said.
‘I started to struggle with sleeping and would have nightmares.
‘I had concerns that Hill was aware of my movements and this led to a fear of seeing him when I was out and about.
‘These last few years have completely changed me as a person and I do not know if I will ever return to the person I once was.’
Hill was also given a four-year stalking protection order, which prevents him from contacting Ms Regester or entering her place of work
Former special constable Hill yelled he was being assaulted by officers when he was arrested just before 9am on March 13 last year.
He also compared himself to George Floyd, who died in Minnesota in the US after a policeman put his knee on his neck for nearly ten minutes, shouting: ‘I cannot breathe.’
But Judge Williams said his behaviour had been ‘bizarre’ and the officers had been ‘incredibly patient’, adding any injuries he sustained were ’caused by himself’.
Hill was also given a four-year stalking protection order, which prevents him from contacting Ms Regester or entering her place of work.
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