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By Zachary Pearlman
Senior Law Clerk

A recent Florida appellate decision (Mcfarlane v. Holness, as personal representative of the Estate of Delroy Junior Mcfarlane) crossed our desks that, on its face, looks like a technical squabble over pleading standards. Dig one layer deeper, though, and it is really a story about blended families, homestead rights, and the quiet ways a well-meaning estate plan can turn into a courtroom fight after someone is gone.

Here is the setup. A man executes what Floridians affectionately call a Lady Bird deed, an enhanced life estate deed that lets him keep control of his property during his lifetime while automatically passing it to a chosen beneficiary at death, all without probate. He does this with his first wife. She passes away. Some time later, he remarries, and not long after that, he dies himself. His second wife, now a widow, opens his estate and separately asks the court to declare the family home a protected homestead, which would preserve her rights as a surviving spouse. In her petition, she mentions the old Lady Bird deed only in a footnote. She does not attach it.

The opposing party pounces on that deed at the motion to dismiss stage, arguing that because the decedent only held a life estate by the time he remarried, there was no fee simple homestead interest to protect and the widow’s claim should be tossed out. The trial court agreed, relied on the deed as an exhibit, and dismissed the case.

The appellate court reversed, and the reasoning is worth sitting with. A motion to dismiss is supposed to test whether the petition, on its own four corners, states a claim. It is not a backdoor invitation for the court to weigh evidence, even evidence the petitioner herself referenced. Because the deed was attached to the motion rather than the petition, the trial court had no business using it to decide the merits of what the deed actually did to the decedent’s ownership interest. That question, the appellate panel said, belongs to a later stage of the case, not the pleading stage.

For those of us who spend our days in the trenches of estate and commercial litigation, this is more than an academic point about civil procedure. It is a reminder of how often the real fight in a case is not about the facts at all, but about who gets to decide when and how those facts are considered. A well-drafted pleading can survive a motion to dismiss even when the other side is holding a document that seems, at first glance, to end the argument. The order in which the court is allowed to look at things matters just as much as what the court eventually sees.

There is also a quieter lesson here for families, particularly blended families navigating second marriages later in life. A Lady Bird deed executed with one spouse does not simply evaporate when circumstances change, and neither do the questions it raises for whoever comes next. Homestead protections in Florida are generous, but they are not automatic, and they can collide in complicated ways with deeds, remarriages, and estate plans that were never updated to reflect a new chapter of life. None of that is a reason to avoid these tools. Lady Bird deeds remain a smart, efficient way to pass property outside of probate. It is simply a reason to revisit an estate plan whenever life changes in a significant way, rather than assuming old paperwork will quietly sort itself out. We tell our clients often that good planning is really an act of care for the people you leave behind, sparing them exactly this kind of uncertainty and litigation at an already difficult time. Cases like this one are a good excuse to pull out your own estate documents, dust them off, and ask whether they still say what you think they say.

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About the Author

Zachary Pearlman, originally from Rockland County, New York, earned his Bachelor’s in American Studies with a focus on the Colonial Era from Ramapo College of New Jersey and interned in the Chambers of Hon. Sandra Sciortino at the New York Supreme Court, Orange County. Currently a 3L at Ave Maria School of Law, he holds a Rewarding Excellence Full Tuition Scholarship, serves as the Managing Editor of the Law Review, and received the Spring 2024 CALI Excellence for the Future Award in Trial Advocacy. Additionally, he is the president of the Saint Thomas More Society, Vice President of the Legion of Mary, and enjoys reading, watching movies, exercising, and bible study.