But an Employment Court judge yesterday determined the actual conditions he worked under made him an employee.
Wellington lawyer Barbara Buckett said other employers who have mislabelled employees as contractors could have a costly problem on their hands.
The court had applied a "reality test", she said, looking at the actual nature and reality of the arrangement.
"So the words on the bit of paper that you sign are not the be all and end all of the question.
She believes treating employees as contractors in the courier business is widespread.
"[Employment court judge Christina Inglis] made some interesting comments around the fact that there has been for quite a long time some form of charade going on."
Though the judge made clear the determination applied only to Leota and did not find all courier drivers were employees, Buckett says similarities will be drawn.
"You'd be very hard put to find an arrangement that wasn't the same, or very similar, to Mr Leota's."
Other industries may be vulnerable to challenge, such as Uber, or the public sector use of consultants and contractors.