Two Whitehorse businessmen have been sentenced to five days in jail after repeatedly defying court orders to stop operating a gravel business on city-owned property and failing to pay thousands of dollars in fines.Yukon Supreme Court Justice Suzanne Duncan imposed the unusual civil contempt sentence against two operators of Annie Lake Trucking Ltd., a family-run gravel company that has been in business for 40 years.“They have intentionally failed to comply with terms of the orders,” Duncan wrote. “They knew they had deadlines but they have continued to disregard those deadlines.”The dispute centred on the company's continued use of a City of Whitehorse quarry despite orders requiring it to halt operations.“A contempt order is a tool of last resort and not to be used routinely as a compliance mechanism or a way to enforce orders,” Duncan wrote. “I have decided.”Court records said Annie Lake Trucking ignored repeated orders to stop operating at the city-owned quarry. A $7,500 fine dating back to 2022 went unpaid, while a subsequent 2025 order requiring the company to clear the property and pay another $5,000 was also disregarded.The court said the businessmen offered no apology or expression of remorse.“The truckers have not apologized to the City or the Court, have not shown remorse, have not provided any reason for non-compliance with orders other than it will cost a lot of time and money,” Duncan wrote.City officials conducted six inspections over 15 months and repeatedly found the company was continuing its operations.“The inspections revealed Annie Lake Trucking continued to conduct a quarrying and excavation of gravel operation for commercial use on the land,” the ruling said. “They continued to store equipment and materials on the land. They continued to live in a mobile home on the land.”.Duncan cited previous Canadian cases dealing with contempt of court, including a 1952 Nova Scotia ruling in Canadian Transport Company Limited v. Alsbury et al.“Once our laws are flouted and orders of our Court are treated with contempt, the whole fabric of our freedom is destroyed,” the earlier judgment said. “We can then only revert to conditions of the Dark Ages where the only law recognized was that of might.”Jail sentences for contempt in civil proceedings are uncommon but have been imposed in other Canadian cases.Federal Court in 2015 sentenced a Niagara Falls, Ont., storekeeper to 14 days in jail and ordered payment of $76,500 in costs and damages after repeated failures to comply with court orders stemming from violations of the Trademarks Act.The High Times Smoke Shop had been sued twice by Trans-High Corporation over unauthorized use of its High Times trademark.