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A 55-year-old man was robbed of his £10,000 hand-made gold watch and broke his hip during an attack in Maidstone.
Weeks later, Jason Orwin died in a separate incident and another man is facing a murder trial at a later date, Maidstone Crown Court heard.
During the first attack, Mr Orwin was thrown to the ground and as he lay writhing in agony was told by one of his attackers: "Give me your watch or I will cut your throat!"
After the robbery, two men were arrested after police tracked their movements on CCTV and caught them sharing a fist pump.
Alan Mulcahy, 29, of Maidstone Road, Chatham, has now been jailed for three years and seven months after admitting the robbery on June 2 last year.
Jack O'Reilly, 30, of Loose Road, Maidstone, received a two-year community order after admitting causing Mr Orwin grievous bodily harm.
Prosecutor Bridget Todd told how Mr Orwin had gone to Brenchley Gardens in Maidstone after finishing work at 8pm.
"Within 90 seconds O'Reilly grabbed him by the throat and as Mr Orwin struggled and twisted he was pulled to the ground."
"He spoke to about 10 people who were sitting in a grass area for about 15 minutes and then two men he recognised came over to talk to him," she said.
"He was drinking a glass of wine and talked to them about general news topics."
The three of them went to buy more booze which they planned to consume by the river.
They made their way through town, via the High Street, and crossed over Palace Avenue and walked to the rose gardens.
"Within 90 seconds O'Reilly grabbed him by the throat and as Mr Orwin struggled and twisted he was pulled to the ground.
"He landed with O'Reilly on top of him. At this point he felt a great pain shooting up his right leg to his rib cage," said the prosecutor
The court heard it was then that Mulcahy walked over to him and said: "Give me your watch or I will cut your throat, you ******* ****."
A terrified Mr Orwin then handed over his 18-carat gold watch, which had a square-face and was encrusted with 32 diamonds.
The court heard that it had been custom-made in New York 20 years earlier and was a gift from his wife.
He was then taken to hospital and treated for a broken hip and was later able to recover the stolen watch after giving cash to a man he later saw wearing it.
Ms Todd said police later viewed CCTV footage and spotted the two sharing "a fist punch in celebration".
Both men were arrested on June 22 and officers then discovered four shotgun cartridges and cannabis at father-of-two Mulcahy's home.
Tom Stern, for O'Reilly, said a psychiatric report revealed he had mental health issues.
He said Mr Orwin had not been lured to the area but the three were "just socialising" and attacked Mr Orwin after having been "goaded" by his co-accused - who denied the allegation.
Judge Julian Smith said it was an "unsettling and deeply unpleasant in its consequences".
"This was a violent attack on an unsuspecting victim that left him seriously injured on the ground."
Mulcahy also admitted possessing ammunition and the Class B drugs.
O'Reilly, who suffers from Asperger's Syndrome, was ordered to carry out 140 hours of unpaid work over the next two years and has to remain indoors for the next four months.
Commenting on the sentencing, investigating officer, PC Alex Peacock of the Chief Constable’s Crime Squad, said: "This was a violent attack on an unsuspecting victim that left him seriously injured on the ground.
"The two men showed no concern for their victim and it is only right that Mulcahy is now starting a prison sentence."
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