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As long as the 16 year old has a valid license the policy should pay out. You will probably be required to add the driver to your policy and will be asked why they weren't listed before.
AnswerIn most jurisdictions an "underage" driver must be listed on the policy and it costs more. In Massachusetts if you allowed an underage driver who resides with you to drive your car and they are involved in an accident then the insurance company will not pay the damages.
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