A major player in an international drugs gang delved straight into the EncroChat underworld within months of his release from jail.
Michael Hailwood was handed a 22 year sentence in 2010 after overseeing cocaine smuggling plots from his base in Amsterdam.
He enjoyed just months of freedom before being caught by detectives for new offences that have now seen him handed a 16 year term.
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Once jailed in the Netherlands, Hailwood has been a prolific figure in the world of drugs during the periods he has not been behind bars.
He had previously operated from Amsterdam for a drug trafficking gang rooted in the north west of England.
As one of the most trusted members of the operation he chaperoned drug mules, often from Eastern Europe, and drove cars that had drugs stashed in secret compartments.
Lancashire Police’s Operation Greengage watched the network as cocaine valued at £10m was smuggled into the UK.
That probe started in November 2006 and followed the network of couriers that would transport funds to Amsterdam to pay for drugs that would be smuggled into the UK - typically inside one of four Fiat Multiplas bought and adapted by the gang.
Unknown to him, Hailwood had two police investigations following his movements.
As well as Greengage, he was being monitored by the Scottish Crime and Drugs Enforcement Agency (SCDEA).
Between October 2007 and December 2007, police in the Netherlands were using wiretaps to listen to his phone calls and established how the Huyton criminal and his associates loaded drug mules onto flights to a variety of UK airports.
In August 2008, after serving part of a 30 month prison sentence for drugs offences in the Netherlands, Hailwood was stopped by Dutch police driving one of the gang’s Multiplas.
The vehicle was seized and later searched by Lancashire detectives where one pellet of cocaine was found. Hailwood was arrested and charged.
He pleaded guilty to conspiracy to supply Class A drugs and was sentenced to 22 years. The wider network was jailed for a combined total of more than 300 years.
The criminal landscape had changed when Hailwood was released from jail at the end of 2019.
His contact book, which included valuable connections in South America, remained relevant though and was a device he used to dangle before active dealers, convincing them to help him regain a foothold in a gangland system he could, in turn, help them move up.
This saw Hailwood link up with a Merseyside operation that was running the drugs trade in Ellesmere Port and had established itself in other parts of Cheshire.
With the shadowy communications network EncroChat the main platform for criminal conversations, Hailwood obtained a device that operated under the codename CardinalTrunk.
Messages retrieved when an international operation infiltrated EncroChat and enabled Cheshire Police to unmask CardinalTrunk as Hailwood.
He was arrested in June 2020 and remanded in custody, ending his short taste of freedom.
Because he breached his licence by engaging in more crime, the 20 months he served before he was sentenced on Friday will not be deducted from the 16 year sentence he was handed after admitting conspiracy to supply cocaine.
The 51-year-old was handed that punishment at Chester Crown Court where Judge Steven Everett told him he may never be released should he commit further serious drugs offences when his term eventually ends.
*An earlier version of this article reported Hailwood was sentenced for conspiracies to supply heroin and cocaine. Hailwood was only sentenced for conspiracy to supply cocaine.
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