A robber dragged a barmaid to the ground as she took £4,000 pub takings to the post office.
Jack Pritchard, 27, grabbed the carrier bag full of cash but as she held on she was dragged to the floor.
The woman was screaming for help before she eventually let go of the bag, Stoke on Trent Live reports.
Pritchard then fled the scene with the money in a terrifying mugging in Silverdale, north Staffordshire.
But the robber left behind his bike and items of clothing which officers were able to use to trace his DNA back to him.
Pritchard has been jailed for three years at Stoke-on-Trent Crown Court.
The court heard that the barmaid worked at the Cotton Mill, in Newcastle, where Pritchard's brother also worked as head chef.
Prosecutor Paul Spratt said the victim had got out of her car on The Parade, Silverdale, on June 17 last year, the day after Father's Day, when Pritchard approached.
He said: "There was a significant level of planning on his behalf, he picked a weekend that he would have known had been more lucrative than any other.
"The victim has worked at the public house for about three years and she has been involved in the banking process on previous occasions.
"She left to use the post office in The Parade, in Silverdale, on June 17 last year at 2pm with approximately £4,000 in a carrier bag.
"Her intention was to bank the largest part and return some of it to the pub as float change and cash. She made one brief visit to a chemist before she got to the post office.
"She parked up and noticed a man with a bike, the defendant, and noticed he had his face disguised with a mask and a hat.
"She made a few steps away from the vehicle with her handbag and carrier bag. The person rode towards her and grabbed the carrier bag and tried to ride off.
"But she held on and was pulled to the floor. She was screaming at the person and for help. She could see people about and then thought she could get stabbed and let go of the bag.
"The person then ran off and she didn't see what direction. His bike was left behind, she was in shock and started to cry once she realised she could have been more significantly hurt.
"This event will have had a significant effect upon her, she was a woman of relatively slight frame."
The woman was left with an injury to her neck, but did not need direct medical treatment.
The defendant was pursued by a shop keeper, who had noticed him many hours before the event, but was unsuccessful.
The money was never found and in his police interview Pritchard answered no comment.
Pritchard, of Station Walks, Halmerend, pleaded guilty to robbery.
Rob Holt, mitigating, said the defendant's mother was terminally ill with cancer.
He said: "He answered no comment to questions put by the police. It is to his credit that after considering legal advice he was in a position to change his mind and pleaded guilty in the magistrates' court.
"It's a brave decision, his mother is terminally ill. He could have pleaded not guilty to await trial and allow him to see see his mum pass away.
"But he has spoken to his mum and said his goodbyes. He has no previous convictions, he has never been in trouble before. To go from that, returning from a year's travel to Australia in February 2019, to this has no explanation.
"There are financial difficulties and alcohol consumption. He is a young man, single with no children."
Judge Paul Glenn said: "Your victim was robbed as she took money from the pub where she works to the post office in Silverdale. This was the Monday after a busy weekend and included Father's Day.
"Officers later recovered some jogging bottoms that you dropped on the floor and your bike was left at the scene and you were linked by DNA to the handle bars of the bike.
"It is not coincidental that your victim worked at the same place as your brother and you accept that you knew who she was and knew something of the banking procedures of the staff at the pub.
"You grabbed the carrier bag, not her handbag. You accept you were under the influence of alcohol. You claim you stashed the money and it is lost.
"I don't accept that. It is quite plain you have an alcohol dependency. This offence is plainly so serious only custody can be considered."