I am not an attorney and this is not legal advice, just a comment:
It depends on what the Trust document states, who the beneficiaries of the Trust are, and what powers the Trustees (and surviving Trustee, successor Trustee) have. I do not believe in any state a Will leaving an interest in property already held (aka owned) by a Trust can overrule the Trust document. If both brothers agree to this, good question for an estate planning attorney. Set up for "one brother," sounds like "keep in the family" rather than any interest to girlfriends or spouses upon death of beneficiaries.
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