Those of us living in the middle of the Sandwich Generation know that the role is rarely just about caretaking and logistics. It is about judgment, advocacy, and sometimes the uncomfortable responsibility of questioning what does not feel right.
There is a common belief that greater financial resources can ease the strain of caring for aging loved ones. While resources can certainly provide access and options, they do not eliminate risk or prevent cognitive decline. And perhaps most importantly, they do not protect families from the possibility that someone in a position of trust may take advantage.
Recent reporting on a lawsuit involving former Major League Baseball Commissioner Peter Ueberroth and his family underscores this reality. According to multiple news outlets, Mr. Ueberroth’s daughter alleged that a long-time trusted advisor and trustee mismanaged significant trust assets and exploited her parents’ declining cognitive health. You can read coverage of the dispute in the NYT, Former MLB commissioner Peter Ueberroth’s daughter tells court trustee misused millions - The Athletic, which details the complexity and seriousness of the claims.
At its core, this situation is not just about wealth or the legal structure of their well-considered estate plan: it is about trust, both the emotional and the legal kind. Trustees are bound by fiduciary duties to act in the best interests of the beneficiaries, to avoid conflicts, and to manage assets responsibly. But when those duties are called into question, particularly at a time when aging individuals may not fully understand what is happening, the burden often shifts to the next generation to step in and ask questions. This is where the Sandwich Generation faces one of its most difficult challenges: knowing when to speak up.
Often, the signs are subtle: something does not quite add up, decisions seem inconsistent, access to information feels limited, and questions are met with resistance. And yet, there is hesitation. The person in charge may be a long-time family friend, a family member, a trusted professional, or someone your parents chose with full confidence years earlier. Raising concerns can feel uncomfortable — disloyal, even. But silence can come at a cost.
One of the most important and most overlooked realities is that having resources and an estate plan does not necessarily insulate a family from vulnerability. In fact, in some cases, it can increase exposure. Larger estates, more complex structures, and concentrated authority in “professionals” can create environments where misconduct is harder to detect and much easier to rationalize. The Ueberroth case is a high-profile example, but the underlying dynamics are not uncommon.
For many in the Sandwich Generation, the challenge is compounded by limited visibility and authority. You may not have direct access to accounts or legal documents. You may not be a trustee or an agent under a power of attorney. Yet you are often the one closest to your parents’ day-to-day reality and therefore the one most likely to notice changes in cognition, behavior, or financial patterns. This type of proximity provides a vantage point to provide insight.
Speaking up does not have to mean making accusations; it can simply mean asking questions, requesting transparency, and often means being willing to say, “Help me understand this,” even when the conversation feels uncomfortable. Early questions when something seems off can prevent larger-scale issues in the future.
It also means recognizing the role of cognitive change. Decline is gradual and often uneven. A parent may appear perfectly capable in one setting and struggle in another. That gray area can make it difficult to determine when intervention is appropriate, but it is precisely in that gray area where vigilance matters most.
Families often rely on goodwill and long-standing relationships. Most of the time, that trust is well placed. But as this situation with the Ueberroth family illustrates, even families with incredible resources and thoughtfully designed estate plans depend on the people carrying them out. When too much authority rests with one individual, and when oversight is limited, the risk of wrongdoing — intentional or not— increases. The takeaway here is not to approach every situation with suspicion; it is to stay engaged.
Request regular updates on the financial picture. Take time to educate yourself to understand the structure of trusts and the decision-making roles. Consider whether there are appropriate checks and balances in place, such as co-trustees, trust protectors, or independent advisors. Suggest regular family meetings to review the decisions made on behalf of the trust at least biannually. And most importantly, trust your instincts when something feels off.
Because being part of the Sandwich Generation is not just about managing doctor’s appointments and homecare, it is about recognizing when advocacy becomes necessary. And sometimes, the hardest but most important step is simply finding the courage to speak up.
