He was found with broken teeth, an infected mouth and heavily matted fur.
But thanks to kind-hearted cat lovers in Norwich, Mr Flat Ears is today facing a brighter future.
The stray tabby - also known as Sycamore Sam - has spent around nine years roaming the streets of Sycamore Crescent, off Waterworks Road.
But over the past few weeks his condition began to deteriorate and it prompted people living on the estate to take action.
Photographs of the matted moggy, who has flat ears, were shared on Facebook and within hours a rescue mission was underway to help him.
Laura Brown, a volunteer with the Lost and Found Cats in Norwich Facebook group, said it took two attempts over the weekend to capture the animal.
The 37-year-old said: 'On Saturday he was found in a shed, but because he is very clever, as soon as we opened the door just a tiny bit he ran out.
'Then one of the ladies who had been feeding him managed to get him in her home and so we went round the next day.
'He was a bit grumpy, but considering the state of his ears and teeth, it was not a surprise.'
Despite his condition, a spokesman for the group said it only took a 'long hug' to calm him down.
He was then taken to Companion Care Vets in Sprowston where his matted fur was shaved off and he was given antibiotics to help treat an infection in his mouth and ear.
Meanwhile, Miss Brown set up an online crowdfunding page to help pay for the cat's dental treatment, with £700 raised by Monday.
She added: 'He is in a good way considering how long he has been sleeping rough for, it could be worse.'
A spokesman for the Lost and Found Cats in Norwich Facebook group said the dental work will take place in the coming weeks.
Mr Flat Ears, who is believed to be around nine years old, is said to have been a stray for almost all of his life.
But he now faces a bright future having been taken in by Jacqui Rebecca, who already fed him regularly.
'He's a gorgeous cat', she said. 'I just want him to have a good life and I am prepared to help him have one.
'I don't know what would have happened to him if it wasn't for the lost cat [Facebook] group.'
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