A former New York Life insurance agent owes New York City more than $400,000 in taxes because he was an independent contractor, not an employee, the city tax tax tribunal affirmed 20 years after the original ruling.

Samuel Friedman argued he wasn’t subject to the city’s unincorporated business tax on the more than $13 million he earned selling insurance as an established field underwriter affiliated with New York Life from 1992 to 2000. The New York City Tax Appeals Tribunal rejected that position Wednesday, saying the arrangement “bears the hallmarks of an independent contractor relationship.”

The tribunal ruled in April …