When most people think about estate planning, they focus on the big decisions: who inherits the house, how to divide accounts, whether to set up a trust. But one decision quietly carries more day-to-day power than almost any other, and it’s the one people tend to rush: who you name as your trustee.

A recent federal case out of Connecticut shows exactly why that choice deserves your full attention.

What a Trustee Actually Does

A trustee is the person (or institution) you put in charge of managing the assets held inside a trust. Think of them as the hands-on manager of everything you’ve set aside. Depending on how the trust is written, a trustee’s job can include:

• Holding legal title to trust property on behalf of the beneficiaries
• Collecting income, such as rent from a property the trust owns
• Paying bills, taxes, and maintenance costs associated with trust assets
• Keeping accurate records and accounting for every dollar in and out
• Distributing money or property to beneficiaries according to the terms you set
• Acting at all times in the best interest of the beneficiaries, not themselves

That last point is the heart of it. A trustee owes what the law calls a fiduciary duty, the highest standard of loyalty and care the law recognizes. They are legally required to put the beneficiaries’ interests ahead of their own. When you hand someone the role of trustee, you are handing them real control over your assets and trusting them to use it honestly.

And that trust can be abused.

When a Trustee Goes Wrong

In May 2026, the U.S. Attorney’s Office for the District of Connecticut announced that a 70-year-old New York attorney pleaded guilty in Bridgeport federal court to embezzling more than $500,000 from a trust he was supposed to be managing.

According to court documents, the situation started ordinarily enough. Back in December 2014, a Connecticut property owner set up a trust to manage real estate, including a commercial building in New Canaan. The attorney was named trustee. His job was straightforward and typical: open a trust bank account, deposit the building’s rental income, pay the costs of running the property, maintain the building, and distribute funds to the person who created the trust. For his services, he was entitled to five percent of the monthly rents plus agreed-upon commissions on new and renewed leases. A legitimate, reasonable arrangement.

Instead, prosecutors say that between roughly February 2016 and September 2022, the trustee siphoned off more than half a million dollars. He did it by writing and cashing unauthorized checks from the trust to himself, his law practice, and his relatives, and by making unauthorized withdrawals and transfers from the trust account. When the trust’s creator died in 2022, the trustee allegedly went a step further, making false statements to the beneficiaries about where the trust’s assets were and what was happening to them.

He pleaded guilty to wire fraud, which carries up to 20 years in prison. He had already paid back more than $509,000 as part of a separate civil settlement with the victims, and is awaiting sentencing.

What stands out here is that this wasn’t a stranger or some obvious scam artist. It was a licensed attorney, exactly the kind of person many families would consider a “safe” choice. The position of trustee gave him direct access to the money, and he abused it for more than six years before facing consequences.

What This Means for Your Own Estate Plan

The lesson isn’t that you should avoid trusts. Trusts are powerful, flexible tools that help Connecticut families manage property, avoid probate, plan for incapacity, and protect beneficiaries. The lesson is that the person you put in charge matters enormously, and that you should build in safeguards from the start.

A few things worth thinking through:

Choose character over convenience. The most important quality in a trustee isn’t financial sophistication or professional credentials, it’s integrity. Credentials did not stop the conduct in the case above. Pick someone whose honesty you trust completely, and don’t assume a title guarantees it.

Consider a professional or corporate trustee, but understand the trade-offs. Banks and trust companies are regulated, insured, and built around oversight and recordkeeping. They cost more and feel less personal, but they’re harder for any single bad actor to exploit.

Build in checks and balances. You don’t have to give one person unsupervised control. You can name a co-trustee so two people must sign off on transactions. You can name a “trust protector” with authority to review the trustee’s conduct and remove them if needed. You can require regular accountings be sent to beneficiaries so problems surface early rather than years later.

Require transparency. A well-drafted trust can mandate that the trustee provide periodic written reports of all income, expenses, and distributions. In the case above, years passed before the misconduct came to light. Routine, mandatory accounting makes that far harder.

Pick a successor and a removal mechanism. Make sure your trust names a backup trustee and spells out a clear process for removing a trustee who isn’t doing their job, without forcing your family into a drawn-out court fight.

The Bottom Line

A trustee holds the keys to assets you spent a lifetime building. As this Connecticut case shows, the wrong choice, or a choice made without proper safeguards, can cost a family hundreds of thousands of dollars and years of stress. The good news is that thoughtful drafting can dramatically reduce that risk.

If you’re setting up a trust, or you already have one and have never revisited who’s in charge, it’s worth sitting down with an experienced Connecticut estate planning attorney to make sure your plan protects the people it’s meant to serve.