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Gordon Freeman formerly owned Watershed Bar and Restaurant and Sequoia 88 restaurant but was found by the Employment Court to have persistently breached employment law.
"Mr Freeman continued to include an illegal clause in his employment agreements stating that staff would forfeit their holiday pay if less than six weeks' notice was given when resigning", the Ministry of Business, Innovation and Employment says.
The Labour Inspectorate lodged the complaint against Mr Freeman with the court and its national manager, Stu Lumsden, says the case demonstrated his team would remove "unfit" employers from the labour market.
"Mr Freeman cynically abused the trust placed in employers, and disregarded the basic rules put in place to ensure everyone in the workplace is getting a fair deal," he said.
The decision came after Mr Freeman was earlier fined by the Employment Relations Authority for the same practice.
In addition to being banned from hiring staff, Mr Freeman and his businesses were ordered to pay $20,000 in penalties, including $7845 to the 23 affected staff.
Mr Freeman was also fined in 2015 when his "employees were forced to take annual leave by being rostered on for a day of annual leave every week without consultation, and without applying for it," the MBIE said.
It said Mr Freeman no longer owns the Watershed Bar and Restaurant nor has any relationship with the business.