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Sean Reed estimates he has racked up around 150 criminal convictions in the last 10 years.
This past year alone, the man who normally lives in Sittingbourne, has had three separate spells in prison serving sentences that range from 80 days to six months.
But the 42-year-old, who has only been out of Sheppey’s HMP Elmley for a short while, was not always moving from cell to cell and courtroom to courtroom.
Born in the picturesque village of Eastling, outside Faversham, he is one of four children.
By his own admission though, he was a “naughty” child – nothing bad, he says, “just a few pranks”.
Fast forward a few years and childhood high jinks had turned into drug smuggling, with Sean being paid £1,500 a time to strap quarter kilo bars of cannabis resin to his torso and transport them here from Spain.
He had only done a few trips when he was caught after a suspicious Dover Priory railway station worker noticed how many Spanish-bound ferry and coach tickets she had sold to the same men in just a few months.
Sean said: “They [the authorities] let us go to Spain, they just knew we were up to something dodgy so all they had to do was wait for us to come back home.
“We arrived back in the country at Folkestone and they let us through customs and followed us into Folkestone High Street.
“The four of us were walking to drop it off and then I saw there were two fellas walking towards me – I knew straight away that was it.
"As I turned around they jumped out of cars, bushes, they’ve got guns as well and they pinned us down on the floor.
“One of us was just 17 and it was his first time doing it and he got caught.”
This led to his first longish sentence in jail (he avoided time when he was caught with vials of Diamorphine stolen from a hospital) at the age of 24.
When he got out 17 months into a four-year term, he moved to Murston and turned his life around after meeting his ex-wife and training as a carpenter.
In fact, that was what he did for the next decade – worked, paid bills, did the weekly shopping and played with his children.
That was until his marriage crumbled and his life fell apart in the process too.
He hit the bottle and settled on a life of shoplifting; playing a cat-and-mouse game with police.
“I’ve not cared about myself for a long time" - Sean Reed
“I’ve not cared about myself for a long time,” he says is the reason for this pattern of offending – not minding if he wakes up alone in a concrete police cell or with a black eye after getting into a scuffle.
So what would change his life? Does he think it’s too late for him to turn things around?
“I’ve got a few ideas and I don’t want to be locked-up again,” is his response, but he is not too forthcoming when quizzed about what this action plan is, possibly it’s one he hasn’t fine-tuned himself.
He would like to visit his mother at some point.
But most of all, he’s happy just to have been out in time for Christmas and, he promises, he has been on good behaviour... so far.