Asked by user in New York.
My friend has insurance on three cars. She has no license but still drives everyday.
Under New York Vehicle and Traffic Law § 509-1, it is a traffic infraction to operate a motor vehicle on the road without a valid license (or to knowingly allow another person to operate the vehicle without a license).
The traffic infraction is punishable by a $300 fine and up to 15 days in jail for the first offense. The penalties become significantly more severe after the first offense.
More importantly, a driver without a valid license is excluded from insurance coverage. In other words, if your friend gets into an accident without a valid license she will be personally liable for any damages that result, regardless of whether or not she has insurance of the vehicles.