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A dad-of-five who could not afford to give his children treats took the drastic decision to smuggle drugs and other items into a prison in return for cash.
Christian Lovell, 42, who coaches children in ice hockey, was to be paid the "modest" sum of £200.
Jailing him for two years and four months, Judge Jeremy Carey told him: "I have no doubt with the benefit of hindsight you will say that was the worst decision you have probably ever made."
Lovell, of Silverbank, Chatham, went to HMP Rochester on March 13 this year to visit an inmate.
Towards the end of the visit, the prisoner was seen to be hiding items down his trousers.
When taken away and searched, he told a prison officer Lovell had "messed up".
Prosecutor James Ross said Lovell smuggled in 61.4g of cannabis resin with a street value of £305 but a "prison value" of £1,220, 2.69g of heroin, 13.2g of herbal cannabis, 47 buprenorphine tablets, a mobile phone and miniature tools.
Items used in drug supply were seized from his car and a small amount of cannabis was found when his home was searched, Mr Ross told Maidstone Crown Court.
Craig Evans, defending, said Lovell, who admitted the offences, became desperate when he was out of work and could not provide the smaller things in life his children asked for.
“That was something he deeply regretted,” he said.
“In his desperate state, he agreed to take the items into prison.
“He took a grave risk for a relatively small amount. He didn’t know what was in the packages.
"In his desperate state, he agreed to take the items into prison. He took a grave risk for a relatively small amount" - Craig Evans, defending
“He is not stupid or naive. He knew they were items that should not be taken into prison.”
Mr Evans said Lovell took class A drugs in his younger life but had turned it around.
He became a volunteer leader with the William Wilberforce Trust, a charity which cared for ex-offenders, and taught at Chelmsford Ice Hockey Academy.
Mr Evans told the judge: “He asks that you take a highly exceptional course and pass a suspended sentence.”
But the judge said: “There is in these kind of cases a need to include a deterrent element to send out a very clear message to those who take items into prison.
“This is a case where the court has no opportunity whatsoever that it can just come down on the side of being merciful.”
Judge Carey said Lovell had put the new life he had built for his family on the line “for a few hundred pounds”.