'Very wealthy' businesswoman who was 'infatuated' with her burglar boyfriend is jailed for insurance fraud after he masterminded £350,000 raid on her home

Daily Mail​

23-05-2025

A 'very wealthy' businesswoman who was 'infatuated' with her burglar boyfriend has been jailed after she fraudulently claimed on insurance for a £350,000 raid that he masterminded on her home.
Emma O'Shea was regarded as a 'soft target' by Dean Ryan, who hired an associate to break into the house and make off with 'high value' diamond jewellery, designer handbags, and envelopes containing thousands of pounds of cash.
But after discovering the raid, the 46-year-old - who refused to believe her partner was involved - tried to con insurers into paying out before fleeing to the Caribbean to avoid having to appear at his trial.
Jailing the mother-of-one for 30 months, a judge branded O'Shea 'selfish' over her insurance fraud following the raid on her £900,000 home in Portsmouth, Hampshire.
It was heard that O'Shea - who now lives in a £1.5 million home - was 'infatuated' with her partner at the time, business owner Ryan, 41.
Among the stolen items from O'Shea's home was a Tiffany engagement ring worth £15,000, Tiffany platinum diamond earrings worth £16,000, and a Tiffany platinum diamond ring worth £22,000.
Tanzanite diamond earrings worth £43,000 were swiped, a chain diamond necklace worth £58,000 was taken, as were diamond earrings worth £34,000 and a £27,000 round diamond necklace.
Several Chanel handbags, each worth up to £10,000, were stolen as well as Rolex watches worth £7,300, plus sapphire diamond rings and eternity bands worth £4,000 and £8,425, and loose diamonds, worth up to £14,000.
After Ryan orchestrated the raid, O'Shea refused to believe he was behind the burglary and tried to 'protect' him when he faced justice.
The couple agreed to trick O'Shea's home insurance provider by smashing a window and claiming it was broken during the break-in, prosecutors said.
When Ryan was due to stand trial for the burglary, O'Shea - who was still seen as the victim at the time - caused the case to collapse by failing to appear in court.
She hid out in Barbados to avoid giving evidence against Ryan and intimidated her housekeeper, who was also due to give evidence, by warning her 'you won't get another penny'.
Mother of one O'Shea denied her offending but on Thursday was jailed for 30 months for conspiracy to commit fraud, perverting the course of justice, and witness intimidation.
Her mother, Sarah O'Shea, 70, went on trial alongside her for perverting the course of justice - by telling her daughter to stay in the Caribbean - and she was sentenced to six months in custody, suspended for 12 months.
Ryan, who pleaded guilty at the start of the trial in January this year, was jailed for four years.
He admitted conspiracy to commit burglary of a dwelling, conspiracy to commit fraud, and perverting the course of justice.
Some of the luxury items stolen in the raid were taken out of O'Shea's safe, which was unlocked with a key
He is already serving a nine-year sentence for an armed robbery which took place in December 2021.
Ryan's associate Gary Cleeve, 45, who burgled the house, denied conspiracy to commit burglary of a dwelling and has been sentenced to three years in prison.
Both Ryan and Cleeve refused to attend the sentencing at Portsmouth Crown Court.
Sentencing O'Shea, Judge William Ashworth said that she 'acted in her own personal selfish self-interest' when she pleaded not guilty to the charges against her, placing a 'burden' on her family.
He said: 'Sadly, Miss Emma O'Shea is still in denial about her involvement in these offences.
'She's very wealthy indeed, and found herself infatuated by Dean Ryan. He found it convenient to have a relationship with her and live under her roof.
'There's no doubt he saw her as a soft target in relation to the burglary before using Miss O'Shea as his own alibi and then playing the role of affronted boyfriend when the burglary was discovered.
'However, when Miss O'Shea realised that the burglar hadn't damaged the property so that her insurance policy was invalid, it wasn't Mr Ryan who was asking her to fraudulently do the window break - quite the reverse.
'It was her asking Mr Ryan to do it for her, which he did.
'She then proceeded to ask Wioletta Krol [her housekeeper] to back up her story that the window had been broken and then hoped that she could then recover the full sum from the insurance company.'
It was heard that Ms Krol had £12,000 in cash stolen but O'Shea has only given her £7,000 back.
The court heard that Ryan moved into O'Shea's townhouse in the Southsea area of Portsmouth after they struck up a relationship in 2021.
The eight-minute burglary which prosecutor Dale Sullivan said took place in the afternoon of March 20, 2022, was committed while Ryan was on bail for armed robbery.
Ryan has had 16 convictions for 34 offences committed between 1999 and 2004.
He colluded with Cleeve, who raided the property while the couple were out.
Mr Sullivan said O'Shea was alerted to the burglary thanks to an alert from her Ring doorbell.
Worried she had been burgled, O'Shea called police but also called her housekeeper Mrs Krol asking her to check her home as she was closer.
Mrs Krol found two ladders propped against the back wall and - crucially - that the dressing room window was open and had not been smashed.
Approximately £350,000 worth of high value jewellery including Tanzanite and Tiffany diamonds, Chanel handbags, Rolex watches and cash were removed from the property by Cleeve.
Subsequently Mrs Krol heard Ryan and O'Shea speaking about the window being open and agreeing they would smash it so it would look better for the insurance company.
The following day, when Mrs Krol went to O'Shea's address to work, she found that the window had been smashed.
Mr Sullivan said O'Shea's insurance policy did not cover theft unless there was force used to enter and no force was used to exit. By the end of April 2022, police arrested Ryan and Cleeve.
O'Shea told police that she did not accept that her partner Ryan was in any way involved, and asked that he could remain living at the house.
In July 2023 Ryan and Cleeve were due to be tried at Portsmouth Crown Court and Mrs Krol and O'Shea were due to give evidence.
Mother of one O'Shea had told the court she was due to be on holiday in France at the time of the trial but was served with a witness summons, ordering her to attend.
She instead went to Barbados at the time of the trial - but told the UK court service a 'flat out lie' that she was 'on the South Pacific'.
The trial had to be aborted after O'Shea failed to attend.
Mr Sullivan said it emerged O'Shea had been communicating with Ryan while he was in custody and relaying information to her daughter in Barbados.
Mrs O'Shea urged her daughter to remain outside of the UK while the trial took place.
Mrs Krol told the court in a victim impact statement that O'Shea was 'like family' to her before the burglary took place.
Sarah O'Shea will have to carry out 150 hours of unpaid work as part of her sentence.