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As a former WC Undewriter with State Fund, we did not allow others to say they were working under somebody else's license. In other words the legal name on file at the CSLB for the party holding the license was the legal name we put on the WC policy.

I would think having a contractor working under another's license and initiating new policies under that license could also create a potential 'double indemnity' issue in which the licensee could be provided coverage under both their policy and that of the other contractor. So I would say this scenario is a no-go for that reason alone, not to mention the several other reasons that stand out about this. Just have him initiate new policies under the auspices of his license status as 'pendiing'...