An ex-fiance of socialite and model Tamara Ecclestone tried to blackmail her for £200,000 – nine years after selling a story about her to the Daily Mail for £10,000.
Derek Rose, 33, has a relationship with Ms Ecclestone, 28, when she was 17 and before he changed his name by deed poll from Jonathan Ketterman.
They split up in August 2002.
In November 2011, having already sold a story about her to the Daily Mail for £10,000 in 2002, Rose orchestrated a blackmail letter with Jakir Uddin, 20, it is alleged.
The men sent an email to Ms Ecclestone's then manager Dana Malmstrom claiming a tabloid newspaper had offered Rose £200,000 for details of their relationship, the prosecution alleged.
But no newspaper had made an offer.
The email was sent while Ms Ecclestone's profile was high – appearing in Billion Dollar Girl, a reality television programme exploring her life as a rich youngster, and after she had generated publicity in charity campaigns.
The defendants were hoping the victim would buy their silence, said William Boyce QC.
"The defendants were in this together," he said.
There were several drafts of the email constructed by the duo to "choose the right words to pressure and intimidate Ms Ecclestone into paying £200,000," said Mr Boyce.
Uddin, a media studies student from the Midlands, sent the email acting as Rose's official representative from the account jakir007@hotmail.
It was sent at 1.03am on 16 November 2011 claiming Rose had been asked by television shows, radio programmes and a major tabloid to talk about Ms Ecclestone, the eldest daughter of Formula One supremo Bernie Ecclestone.
The email said: "While my client has not spoken about Tamara in 10 years and has let her live her life we have been approached by a major tabloid with a life changing offer of £200,000 to go ahead with the story and disclose all…
"My client has asked me to contact you to explain what he is going through and what the press are intending to do.
"My client is a quiet family man and he doesn't need the headache of this story coming out because it would be embarrassing for both our clients."
The barrister said the email went on with "pernicious" implications about damage to Ms Ecclestone's reputation.
Part of the email was written in bold but not read out in court.
It referred to an "incident".
The tone of it was "you don't really want that in the press whether it's true or not," said Mr Boyce.
The defendants allegedly wrote they would be happy to discuss "a non-release fee" and sign a confidentiality contract.
But they also gave a deadline of the following Friday when they claimed they had to answer the tabloid's offer.
Rose, of Arlington Road, Camden, London, and Uddin, of Old Walsall Road, Birmingham, both deny blackmail.
The Daily Mail paid Rose £10,000 for his story in 2002.
An email he sent to Ms Ecclestone in August that year after they broke up was given to the jury.
The prosecutor did not read the three pages aloud but described the content as "extraordinarily offensive".
The email, which police retrieved from Rose's computer, "contained all sorts of allegations" Mr Boyce said.
"You may think he professed to love her," said the QC.
"In fact he loathed and despised her."
Rose was the "driving force" behind the scheme and planned to keep £150,000 if they were successful, said Mr Boyce.
Ms Ecclestone told the court after receiving the email in November 2011 she just wanted Rose "warned" about his behaviour and not necessarily arrested.
She said she discussed the email with her father and that none of her other boyfriends had sold stories about her.
The seven men and five women of the jury heard that Rose and Uddin blamed each other upon arrest.
The trial continues…