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A thug manipulated his girlfriend by threatening to "terrorise" her and repeatedly saying he would kill himself.
Tony White, of Ramsgate, mentally and physically abused the young woman, before launching a campaign of harassment from inside his prison cell.
The 36-year-old also spat in her face, dragged her from a car and jumped on her windscreen, causing it to smash, showering her in glass.
The woman was driven to suicidal thoughts and left feeling like she was "constantly walking on eggshells", while they were together, Canterbury Crown Court heard on Friday.
When the 19-year-old discovered suspicious texts on White’s phone she told him the relationship was over.
But White “made the first of a series of threats that he’d kill himself if she left him”, prosecutor Peter Forbes explained.
The macabre pattern quickly became a weekly event, where White sent images of him cutting, bleeding, and handling boxes of pills.
After he made a barrage of unfounded allegations she began to distance herself as White's paranoia intensified.
He sent graphic images of his self-harming, alongside the words “goodbye, just remember I am sorry and I love you” and “I hope you are happy now”, the prosecutor said.
During a night out with friends, he hunted her down, spat in her face and pushed her into a wall.
He dragged her from a friend’s parked car and ordered her to go home with him, during the disturbing ordeal in January last year.
Becoming increasingly fearful for her safety, the woman ended the relationship the same month, triggering White’s fury.
About two weeks would pass without incident, when suddenly White suddenly called her repeatedly.
When she eventually answered her friend recorded his tirade threatening to harm her, her family and himself.
He said: “I hope you’re actually happy because I’m going to smash your brother everywhere.
“I’m going to terrorise your whole life - I’m going to terrorise you.
“I’m going to beat you.”
When she eventually agreed to meet days later White’s actions became physical.
Attempting to speak with him through her car window, White tried opening the door and she refused.
“He went on to attack the rest of the car," Mr Forbes added.
"By the end he was jumping on her windscreen and stamping on it, causing it to break.”
Following his arrest, White called the woman from HMP Elmley to make vile threats and attempted to convince her to stop supporting the prosecution.
"You must accept your relationship with her is over and there are no circumstances whereby you should communicate with her in the future..."
He continually shouted at her, again making threats to kill himself, and declared: “Now you have caused a war.”
White pleaded guilty before trial to a number of charges, including controlling behaviour within a relationship between summer 2021 and January 2022.
He also admitted criminal damage, sending malicious communications, assault and perverting the course of justice.
But a judge adjourned sentencing last year for a psychiatric report.
On Friday, a doctor told the court White, who has 35 previous convictions, suffers from a psychological disorder, for which he is now medicated.
Phil Rowley, mitigating, said White feels his “feet are on solid ground” following the recent diagnosis, which “could be a springboard to a far better personal future”.
Handing down 39 months in custody, Recorder Michael Turner told White he “waged a campaign of harassment, intimidation and violence” against her.
“You must accept your relationship with her is over and there are no circumstances whereby you should communicate with her in the future,” he added.
White, formerly of the Plains of Waterloo, was also made subject to a five-year restraining order.
The year and one week already spent on remand will be deducted from his overall sentence.