The Newsletter

Held in Trust

Safeguarding what belongs to others.

Plain-English essays on trust administration, estate planning, and fiduciary duty — the craft of holding what belongs to someone else, and answering for it. New essays land here first, then on LinkedIn. Subscribe below.

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The Agreement That Cost Two Children $35 Million Each

July 30, 2026

A family unanimously agreed to end Mom's QTIP trust early and hand everything to Dad. In McDougall v. Commissioner, the Tax Court just priced that handshake at $35,141,321 per c...

The Age Your Plan Assumes You Die

July 29, 2026

Nearly 90% of advisors accept the age-90 or age-95 default in their planning software. For a trustee owing impartiality under N.C.G.S. 36C-8-803, that unexamined number quietly ...

The Trustee Who Drained a Trust to $41 and the Penalty He Couldn't Argue Down

July 27, 2026

A disbarred attorney emptied the trust he drafted, then argued he was too broke to pay the penalty. In Moramarco v. Nowakoski, California held that Probate Code 859 doesn't ask ...

Conagra's Dividend Cut: The Yield Was Never the Safety Net

July 24, 2026

Kristian Pfeffer on Conagra's 50% dividend cut and $2 billion goodwill writeoff, and why a trustee who bought the yield instead of the business gets caught flatfooted.

The Marital Deduction a Widow Almost Lost to a Checkbox

July 23, 2026

An IRS private letter ruling let a grieving spouse fix a botched QTIP election under Sec. 2056(b)(7). The relief exists, but the cleaner path is a protective election the first ...

The Handoff Hidden Inside a 'Trump Account'

July 22, 2026

Kristian Pfeffer on Sec. 530 'Trump Accounts' and the moment they quietly become a traditional IRA — handing an eighteen-year-old both the money and the duty to manage it.

The Alpha That Actually Reaches the Family: Why Tax Optimization Is Becoming Core Fiduciary Work

July 20, 2026

Cerulli Associates finds tax optimization is now the top development priority for wealth platforms, two years running. For a trustee, that isn't a product trend — it's a duty th...

A Fiduciary Mindset, Learned the Hard Way: From the 82nd Airborne to the Trust Office

July 19, 2026

Kristian Pfeffer on how six years as a U.S. Army logistics officer — accountable for $15M of other people's property — became the foundation for a career in trust administration...

When a Charitable Trust Becomes a Shelter: The IRS Draws a Line on CRATs

July 16, 2026

New IRS regs make certain CRAT schemes listed transactions, with steep penalties for skipping disclosure. Call it more paperwork if you like — a CRAT that puts the charity first...

Who Decided Your 401(k) Should Own SpaceX?

July 15, 2026

A mega-IPO with no real price discovery, billions in losses, dual-class shares, and immediate index inclusion — landing in retirement plans by default. A fiduciary owes benefici...

The Wall That Didn't Hold: Control, Irrevocable Trusts, and a $111 Million Lesson

July 15, 2026

In C.S. v. R.H., a husband placed $111 million in irrevocable trusts yet kept trustee and investment control. A New York divorce court folded it into the marital estate. The tax...

The Edge Goes to Who Trains the AI, Not Who Commands It

July 14, 2026

Twilio's turnaround is a preview of a wider shift: AI is a labor resource, and the advantage belongs to the people who teach it — not the ones who bark orders at it.

Who Takes the Trust Nobody Gets Rich On?

July 13, 2026

Trust companies keep exiting special needs trusts or pricing out everyday families. A (d)(4)(A) trust protects a child's SSI and Medicaid only if someone will administer it — an...

When Silence Becomes the Violation: The IRS Lists Abusive CRAT Transactions

July 12, 2026

The IRS named certain charitable remainder annuity trust transactions as listed transactions. The structure served real donors too — but now non-disclosure, not the strategy its...

How One Founder Erased $8 Million in Gains — and the Fine Print of Section 1202

July 11, 2026

IRC §1202 lets founders exclude gain on qualified small business stock, and trust stacking can multiply it. A powerful tool for concentrated wealth — but only if the holding-per...