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James Toomey, Executor Discretion, 110 Iowa L. Rev. __ (forthcoming, 2025), available at SSRN.

I hereby grant my executor the power to alter my will to reflect my most likely recent intent.

Notwithstanding the mysteries that can attend multiple aspects of estate planning, some things—such as the precepts that deeds are not wills, revocation is permitted, and takers must survive—seem plain. The near-absolute supremacy of Testator Intent fits within this rough set of axioms. Cases instruct that, elusive though it may be, it is that intent alone that matters, and not that of any judge, jury, or creditor; disappointed spouse or disinherited heir. Indeed, the principle has become the rhetorical stuff of earth and sky both, with the Testator’s intent cast as the cornerstone, the lodestar, the keystone, the polestar, the crown jewel, the very light that guides. Less often questioned is just how far and brightly that North Star actually shines, and at what temporal and comparative remove.

Professor James Toomey seeks consistency and tests fidelity to Testator Intent in Executor Discretion, admonishing that lawmakers should be every bit as aggrieved by the effectuation of will terms that reflect expired intent as reformers have been, for decades, about the rejection of intended wills on formalistic technicalities. “Whenever a will is probated [that . . .] no longer represents what the testator would have wanted, wills law fails on its own terms.” (P. 1.) If and where so, the autonomy, identity, and freedom that testamentary intent captures also fail, and stars fall to earth.

Preliminary confessions. Article titles can be as deceptive as book covers. Here, I first (and wrongly) assumed that Executor Discretion would catalogue existing but rarely flagged de jure or facto administrative space where it already operated—e.g. deciding between distribution in cash or in kind, through power of sale—then urge extension, retrenchment, or justification. That seemed intriguing, especially could such hidden discretion prove powerful enough to undermine or uphold wholistic views of the estate plan’s intent, including work at gray margins to remediate the ill-effects of planning neglect. But Executor Discretion is much more direct. It attacks the stale will by affording executors rights to react to expired intent by adding to, subtracting from, or altering the will itself, post-death, where the will itself so authorized. When I realized this far greater project, I instinctually blanched. This version of “executor discretion” seemed oxymoronic, a sense aided, perhaps, by the traditional role reinforcement found in the very language of wills. On its face, a “Last Will and Testament” already reflects the recency, primacy, and intent of its author—the testator—relegating executors to supporting roles as discretion-less functionaries merely “executing” the hope/wish/intent—the will—of another. Further reading forced deeper thought.

Prof. Toomey carefully grounds expired intent failures within theory and practice, including what he sees as their inexorable exacerbation given such sociocultural changes as heightened volatility in property values and the cognitive debilities (thus reduced capacity to amend) posed by increased life expectancies. This discussion is insightful, as are his observations about the inadequacy of alternate planning techniques or presumptions about revisions of intent stemming from discrete changes of circumstance. His work reminds readers that even fixes that work “most of the time” and with efficiency should pale against those that may appear startling but permit a sharper view of intent (assuming acceptable costs, but more on that later). Highlighting the near-sacrosanct nature of the intent core while taking seriously the difficulties of an approach directed by what this testator (not most of them) would have wanted could she have expressed it validates the piece. But Executor Discretion works even harder by encouraging a different and deeper question than how much discretion executors should hold. By replacing a call for potentially time-consuming, difficult, and costly objective reform—e.g. legislative safe harbors or an enhanced set of presumptions—with an explicitly subjective grant of discretion within the subject will itself, Prof. Toomey also forces readers to confront how much intent-driven freedom the law is actually willing to afford to those who write them.

“I hereby grant my executor the power to change my will to align with my most recent and likely intent; I love and trust my executor, and really, really mean it.” Readers might be torn over how to react, and that is exactly the point. Not all scholarship need yield incontrovertible answers to all questions or proffer unassailable cures. Reading that sort can feel like being shoved through a cow chute with no room for creative detour or wonder. There are many questions prompted (and many but not all answered) here, which is part of why the piece keeps singing in the ear.

But while it is always critical to foreground Testator Intent, it is also worth considering what it is set against and at what cost. Assuming the travesty or at least peril of expired intent: who is and should be its least cost avoider, and how; might directed trusts, careful decanting, or outright gifts coupled with hopes to the loved and trusted work as well or better; could this “cheap, fast and easy” intent-based proxy create more problems than it solves, more litigation than it avoids, more costs than it saves, a lengthier process for probate, just another technique for the undue who overstep. What effect could this hold for Parol Evidence, the Statute of Wills, the Statute of Frauds, the secret trust; would requiring periodic re-ups for or imposing a shelf life upon wills feasibly avoid or ameliorate matters, or at least, improve estate planning; could this sort of blanket clause absolve lawyers and clients from the hard work of doing better? Whether or not one agrees with its conclusion, that Executor Discretion evokes as well as answers, and inspires ongoing thought, is part of its power and its joy.

Discretion simultaneously suggests future action and traces back to intent, itself never unabridged. No matter how clearly expressed, testators cannot demand crimes or flout public policy. The spouses they exclude still may elect; the guardians they name are only suggestions; the personal representatives they select will fail if disqualifying facts emerge; the abuse of discretion they excuse is a nullity and the murder they excuse is, too. But one wonders what the law should allow testators to both want and accomplish in extension of self, and how far their power to extend discretion, post-death, should extend. This particular grasp—a grant of testamentary authority to the executor—may well exceed its reach. But agree with Prof. Toomey or not, the care with which he considers outcomes and constructs his case is undeniable. This suggests that outright rejection even to consider his proposal may rest more with basic distrust of human nature than with that which he has built. How much testamentary freedom is free? The conversation is worth having.

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Cite as: Katheleen Guzman, Discretioners, JOTWELL (March 28, 2025) (reviewing James Toomey, Executor Discretion, 110 Iowa L. Rev. __ (forthcoming, 2025), available at SSRN), https://trustest.jotwell.com/discretioners/.