I would be calling my EIC prior to entering into such a transaction.
A trust would not automatically shield the executive officer from Regulation O considerations. See: CONTROL OF COMPANY OR BANK--Executor, Trustee, or Beneficiary of Estate or Trust
https://www.fdic.gov/regulations/laws/rules/7500-1500.htmlAny loan that is made by the bank that benefits an insider (even indirectly) is considered covered. So the question then becomes if the bank makes a loan and the executive officer purchased part of it, would it be covered. I am not sure that there is a staff opinion on that issue, hence I would pre-clear it with my EIC.