Serving as a Trustee of a Trust is difficult. In the case presented, a trust beneficiary alleged that the trustee—his aunt—breached her fiduciary duty. The trust beneficiary retained an expert in connection to this claim and this did not go well for either the beneficiary or damages expert. The article summarizes the case, provides a road map and an admonition to experts in these types of cases regarding what is needed, and the perils of using AI.