Even a $91 Million Coach Was Told to Put Down the Chatbot
Estate planning lessons do not show up in the sports section. One did recently, and it was worth holding onto.
ESPN ran a long piece on the legal fight between LSU, coach Lane Kiffin, and the SEC. Most of it is legal maneuvering. But there is a small exchange buried in there that has nothing to do with the sport. Tom Mars, a well-known attorney familiar with the dispute, recounted telling Kiffin — a man reportedly working under a $91 million contract — that he ought to have "a top-notch lawyer on speed dial" instead of asking ChatGPT for legal help.
Sit with that for a second. A career, a program, tens of millions of dollars on the line, and the reflex was still to type the question into a chatbot until someone who does this for a living talked him out of it.
If that is a bad idea at $91 million, it is a bad idea for the estate you have spent a lifetime building.
Why capable people try it anyway
It is worth being fair about the appeal. These tools are fast. They are available at two in the morning. They never make you feel foolish for asking a basic question, and they answer everything with the same calm confidence. If you are the kind of person who has spent a career solving your own problems, handing your will and trust to an AI tool can feel like the efficient, modern move.
The trouble is what happens next. We see the results when a family brings us a plan that a chatbot put together, and planning a large, complicated estate turns out to be one of the things these tools do worst.
Where it goes wrong for someone in your position
Start with the obvious problem: an AI model does not know you. It assembles a generic document from patterns it has seen elsewhere. It has no idea that your real estate spans two or three states, that a large chunk of your net worth sits in retirement accounts, that you have a second marriage and children from the first, or that one of your kids should be provided for differently than the others. You get the average answer. Your situation is not average.
It also does not know Florida, and Florida is unforgiving about the details. A will or trust is not valid just because the language sounds right. It must be signed, witnessed, and notarized in a particular way, and a self-proving affidavit adds its own requirements on top of that. Botch the execution, and you can end up with a beautifully worded document that does nothing when your family finally reaches for it — exactly when no one can fix it anymore.
Then there is the retirement-account issue, which is where the most expensive mistakes tend to show up. For a lot of the families we work with, IRAs and 401(k)s are among their biggest assets. Since the SECURE Act did away with the old "stretch IRA" for most of the heirs, an inherited retirement account generally must be emptied within ten years, often landing in your children's highest-earning, highest-tax years. Name the wrong beneficiary or point an IRA at a trust that was not drafted to receive one, and you can trigger a tax bill that swallows years of careful saving. A chatbot will sail right past that. It does not know how to raise it, and you do not know what to ask.
That's really the deeper issue. Good planning is built as much on the questions you did not think to ask as the ones you did. AI has no judgment and no stake in the outcome. It will not see the family conflict coming. It will not tell you what it does not know. It cannot be your fiduciary; there is no attorney-client relationship, and no one is answerable if it is wrong. Worse, it is just as confident when it is wrong as when it is right — and it is sometimes flatly, completely wrong, statute citations and all.
The cruel part is when the mistake shows up. A flawed plan almost always fails quietly. No one notices until there is a death, an incapacity, or a fight over money, and by then you are not around to correct it. You will not pay for the error. Your spouse and your children will, in probate, in legal fees, and in taxes that better planning would have spared them.
The one way to use AI here
If you want a role for it, keep it small. Let it help you get organized and sharpen your thinking before you sit down with a professional. Ask it to explain a term. Ask what issues someone in your circumstances should be considering. Show up prepared. Then take those questions to someone who can actually stand behind the answers.
The wealthier and more tangled your situation, the less sense it makes to trust it to a tool that doesn't know you, doesn't know this state, and can't be held responsible when it counts. A multi-million dollar estate deserves the same instinct that lawyer had for his client: a real one, on speed dial.
That's the whole of what we do at Beacon Legacy LawTM. Our practice is led by a specialist Board Certified by The Florida Bar in Wills, Trusts and Estates — a credential only a small number of Florida attorneys hold — and our attorneys build every plan around your family and your assets, not a template.
If you've been meaning to get this handled, or you have a nagging feeling the plan you already signed wouldn't hold up, come in for a Vision Meeting. It's an unhurried conversation about what you've built and how to keep it intact for the people you're leaving it to. That's the job, and it's not one to hand to a machine.
