Former fisherman Barry Domsalla, 59, from Eastbourne, was sentenced to ten years following one of the biggest ever drugs seizures in Scotland.
And at Dumfries High Court, Domsalla's brother-in-law, chef Michael Harris, 49, from Pevensey, was given eight years in prison.
They were charged with supplying cannabis after smuggling 166 bales of the drug with a weight of five tonnes into Portpatrick Harbour in South West Scotland, on board a 37ft fishing trawler called Lady Ann.
Ahighly dangerous and elaborate sting, codenamed Operation Fingers, successfully brought the men to justice.
Members of the smuggling gang had no idea Lady Ann's skipper was a customs informer and his crewman an undercover police officer.
As a result of the swoop last September, two Dutchmen who sailed the drugs from the coast of Morocco on board a 48ft yacht called the Spirit of Shamrock to a meeting point off the island of Islay, Inner Hebrides, were also jailed.
Skipper Ronald Keiser, 35, was sentenced to ten years. His crewman Richard Nobel, a decorated Gulf War veteran who had served in the Dutch Royal Navy, was jailed for eight years.
They too were charged with supplying cannabis although they were cleared of illegally importing the drug.
The Lady Ann's skipper, the customs informer known only as Robert, received a £25,000 reward for his part in the operation.
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