A Crown Court judge said the attack was so brutal the victim could easily have been killed were it not for the intervention of a member of the public who witnessed the scenes from his bedroom window.
The robbers - 32-year-old Michael Kelly and Michael Green, also 32 - appeared for sentence at York Crown Court on Wednesday after admitting robbery.
Kelly also admitted attempted robbery in relation to a second incident on the same night – when he threatened to throw another man into Whitby Harbour if he didn’t “turn out his pockets”.
Prosecutor Michael Cahill said the first robbery victim was “scared for his life” after being floored by a mighty blow from behind.
He had been lured out of Jk’s bar on Wellington Road by Kelly and Green, both from Hull, who asked the Whitby man if he fancied joining them for more drinks at another night spot as Jk’s was closing for the night.
The three men left the bar and were walking along Church Street, just past Whitby Swing Bridge, when the victim was suddenly struck from behind to the side of his face.
The force of the blow knocked him to the ground.
He was then kicked to the head and ribs before one of the attackers ran away.
“The other remained and demanded either his bank card or his money,” said Mr Cahill.
A man in a nearby property “heard a commotion” and saw the scenes unfolding from his bedroom window just after 1am on November 17, 2019.
“He shouted at them to stop kicking (the victim),” added Mr Cahill.
“He was concerned they would kill him.”
The witness heard one of the robbers shouting: “Give us £70!”
The drunken robbers finally fled, leaving the battered and bloodied victim with injuries including broken teeth and bruising and swelling to his head and body.
Meanwhile, another named local man was out on a walk because he couldn’t get to sleep.
“He was walking near the harbour and as he passed the Jolly Sailors pub, he noticed two males,” said Mr Cahill.
The named victim was wearing headphones but lowered them as he thought Kelly was “asking him something”.
“As he did so, he was hit by Kelly a couple of times,” said Mr Cahill.
“He was told to turn out his pockets or he would be thrown into the harbour.”
Kelly then told the victim “to get into a nearby alleyway” while demanding “his pockets be emptied”.
However, on this occasion the victim managed to get away across the swing bridge.
Green, of High Street, Hull, denied playing a part in the attempted robbery and the prosecution accepted this plea.
The first robbery victim said he had to pay £500 for dental work on his broken teeth.
He added: “During the attack, I did not know what to expect and feared the worst.”
“He was bruised and swollen and in pain for some weeks after the attack,” said Mr Cahill.
“He was due to start a new job (a few days after the attack) but had to call in sick on his first day of work.”
He said the victim “could do nothing to stop (the robbers) and was scared for his life”.
Mr Cahill said that following the attack, the victim had checked his online bank account and noticed there had been a withdrawal of £50 from a cash point on that day, but “couldn’t recall doing that himself”.
Kelly, of Blisland Close, Bransholme, had numerous previous convictions for offences including robbery, burglary, serious violence, fraud, being drunk and disorderly, and conspiracy to steal.
Green, 32, had also served a previous prison sentence for assault with intent to rob and had a previous drink-related conviction.
Mark McKone, for Kelly, said his client, who was in employment, had a drug and alcohol problem.
Jonathan Harley, for Green, said his client - by trade a fisherman – had acted “out of character” and was otherwise a “hard-working and decent man” who had lately been working at a pub in Hull.
Judge Sean Morris said both men “knew that (the robbery victim) had been to the cash point (and) you robbed him”.
He added: “The kicking of somebody with a shod foot can kill and that is what the onlooker thought might happen, and it’s very, very fortunate that he shouted at the pair of you because otherwise (the victim) might not be here.”
The judge told Kelly: “Having left your victim injured and bloodied on the ground, you went on to try to rob another man.
"Fortunately for him, you didn’t succeed in robbing (him).”
Kelly was jailed for four years and Green, who was “not the instigator” and had less previous convictions, was jailed for three-and-a-half years.
Both men will serve half of those sentences behind bars before being released on prison licence.