A former boxer who competed for England squandered his chance for a "promising career" after turning to the murky world of drug trafficking.
Craig O'Brien, 33, from Rochdale, Greater Manchester, was first jailed in 2010 for five years in relation to a "neighbour dispute".
But while behind bars he was "taken under the wing" of a "more sophisticated criminal", Manchester Evening News reports.
O'Brien then became a link in the drug supply chain, and is now back in prison after pleading guilty to trafficking five kilos of cocaine.
The 33-year-old was arrested on suspicion of drugs offences last summer, but police then discovered far more than they originally expected.
Detectives found incriminating messages on the encrypted messaging service, Wickr, on two of his phones, in June.
O'Brien spoke with contacts about how much cocaine they wanted wishing to buy; the quality of the drug; and prices, Minshull Street Crown Court heard.
In other messages, he said he could get new devices for his associates to use following the Europe-wide hack into the Encrochat network in June 2020.
Tom Challinor, prosecuting, said messages were recovered on the Wickr app.
"Included in these messages were images of kilos of cocaine, compressed into blocks, some which were embossed with logos which signified their origin," he said.
"One account asks the defendant for a 'job' for a friend of his who is going to buy from him if he 'liked it' and there was a possibility to 'get 25 for a kilo'.
"It was suggested by the user that he could sell the drugs on for Mr O'Brien if his customer liked them and could make Mr O'Brien some money.”
In other messages, the account requested cutting agents to break down the drug.
The court heard of messages from an associate of O'Brien who wanted to supply him with drugs and said there was 'three of something for 37.25'.
The inference was that there were three kilos of cocaine for £37,250, the court heard.
The next morning, O'Brien was in talks with other users about flogging the drug - including 'Twittwoo2018', 'NOlive89' and 'Dupree01234'.
"Another conversation on June 10 was uncovered, with another user - 'MrH197' - with 'MrH' talking about money he [the defendant] owed him," Mr Challinor told the court.
"'MrH' noted the 'boss man' said the defendant had what 'Mr H' owed him.
"He also said 'MrH' could do 100 a week - the inference being 100 kilos of cocaine. It has been agreed that Mr O'Brien trafficked five kilos of cocaine."
The court heard there were further messages suggesting O'Brien could get more encrypted devices following the hack into the Encrochat platform.
He was arrested in December last year and provided a 'no comment' police interview.
O'Brien was said to have a previous conviction for wounding in October 2010, for which he was jailed for five years.
Mitigating, Imran Shafi QC said: "In 2010 he was a young man, he went to prison for five years, he was of a young age at that time.
"It was a neighbour dispute which escalated and he lost his promising career as a boxer for England.
"Whilst in prison he was taken under the wing of somebody more sophisticated."
Mr Shafi said his client was described in his character references as a 'considerate and kind man'.
He said time in prison would allow O'Brien to 'reflect on his life'.
Sentencing, Judge Maurice Greene said: "The evidence against you essentially comes from telephone messages that took place between you and either people you were supplying or others supplying you.
"And the messages took the form of discussions about how much cocaine you could obtain and what sort of price. Many thousands of pounds, perhaps.
"It was agreed by the prosecution that the amount involved was five kilos over this particular period of time.
"I have read your character references and your letter, and you are remorseful, and you have worked and been a valued member of society. You have had considerable difficulties.
"Because of that I am able to reduce the starting point of cases of this kind."
O’Brien, of Moorland Crescent, was jailed for four years and eight months, after pleading guilty to conspiracy to supply class A drugs.
A Proceeds of Crime Act hearing was set for June 30.
