Probate Litigation

Using AI to Craft Legal Arguments

May 23, 2025 | by Chepenik Trushin LLP

Artificial intelligence (“AI”) is a great tool to assist people with a variety of tasks. For example, AI can create grocery lists and corresponding recipes, offer advice for difficult situations, or even draft an email to a colleague. But can AI do the work of an attorney?

In the Matter of Phylliscita Ismay Samuel, the court had to address a lawyer’s careless use of AI in a contested probate proceeding. In this case, a decedent executed a purported prior will in 2012. In 2014, the decedent was the subject of a guardianship proceeding where she was adjudicated incapacitated and the court appointed Samuel as her guardian. Thereafter, the decedent executed the purported 2014 will which was challenged and became the subject of this case. The party challenging the will, Osborne, sought summary judgement and dismissal of Samuel’s petition and denial of the propounded 2014 instrument, alleging that the decedent lacked capacity at the time of execution, and that the instrument was procured by fraud, duress and undue influence by Samuel and others.

While attempting to challenge the will, Osborne faced a huge problem with his case. Osborne’s attorney submitted documents which contained fictional and/or erroneous citations because he relied on generative AI to draft these documents. In other words, the AI which Osborne’s attorney used had “hallucinated” or made up the cases relied on in the legal arguments made to the court.

Your legal responsibilities as a named personal representative in estate planning documents

April 7, 2022 | by Chepenik Trushin LLP

Est. of Pounds v. Miller & Jacobs, P.A., No. 4D21-1362, 2022 WL 39211 (Fla. 4th DCA 2022).

If a will does not specify who should serve as personal representative of an estate, parties can fight over this position through litigation. But what happens if one person obtains a settlement on behalf of an estate, and then another person is appointed as personal representative? The court answered this question in Estate of Pounds v. Miller & Jacobs, P.A., No. 4D21-1362, 2022 WL 39211 (Fla. 4th DCA 2022), giving us insight into why these situations are problematic and why good estate plans need to be carefully drafted.

The decedent died in a motorcycle accident, leaving behind his minor child as the sole heir of the estate. The child’s mother and the decedent’s mother both showed interest in serving as personal representative of the estate, which comes with certain perks, such as earning a personal representative fee, and responsibilities, including distributing estate property. The child’s mother was not married to the decedent.

Are you a “Dutiful Child”, who is a caregiver for your loved one? The Florida laws explained.

February 9, 2022 | by Chepenik Trushin LLP

Florida’s ‘Dutiful Child’ Exception

Throughout life, relationships and priorities often change, necessitating amendment to one’s Last Will and Testament to reflect these changes. However, sometimes these testamentary changes raise questions as to the testator’s motivations for the revisions, leading to a will contest. “Undue influence” upon the testator is one basis for challenging the validity of a will, trust, or other testamentary document. While litigating the issue of undue influence can be complex, the basic concept is straightforward: an individual is accused of improperly persuading a (often vulnerable and elderly) testator to draft or amend their will for that person’s individual benefit.

Florida courts consider several factors when assessing claims of undue influence over a testator, including the beneficiary’s arranging for the testator to prepare a will, knowledge of the contents of the will, and presence during the execution of estate planning documents. On paper, these factors seem like red flags pointing towards a finding of undue influence. Yet in reality, these are common actions of adult children simply caring for their elderly parents. So, how can an adult child helping their parent with estate planning justify these actions when faced with an allegation of undue influence?

Handwritten Wills and the Importance of Witnesses – What you need to know because it is complicated

March 15, 2021 | by Chepenik Trushin LLP

Larry King’s Handwritten Will Ordeal

The recent passing of the broadcasting legend, Larry King, has resulted in his family not only mourning him but also fighting amongst themselves over his true last wishes. Larry, together with his wife, Shawn Southwick King, had executed estate planning documents in 2015, where he named her the personal representative of his estate. However, the couple faced some difficulties and Larry filed for divorce in August 2019. Just two months later, he executed a new handwritten will, leaving his entire estate valued at $2 million dollars to his five children. Two witnesses also signed their names to the hand-written will.

Larry’s eldest son, Larry King Jr., submitted the 2019 will to the court and has petitioned to be appointed the temporary administrator of Larry’s estate. However, Shawn has filed an objection to the 2019 will, claiming that the will is invalid and that Larry King Jr. exerted undue influence over his father towards the end of his life, and insisting that the 2015 will is the valid one.

Enforcing a contract to create a Will is complex – read the details

November 4, 2020 | by Chepenik Trushin LLP

Contracts to Create a Will

A last will and testament must be the consequence of a person’s free will (which is why they are aptly referred to as “wills”). Nevertheless, a person may execute a contract during life to include certain terms and/or beneficiaries in their will in exchange for goods or services.

Enforcing a contract to create a will is more complex than enforcing a normal contract. With these types of agreements, it may be impossible to tell whether the testator lived up to his or her side of the bargain until their estate plan is revealed after their death. Additionally, the terms of a will do not come into effect until death, so there may not technically be a breach of the contract until the decedent’s death. Further, if you were supposed to be a part of the decedent’s estate plan, but were not included, it’s possible you may never even receive notice regarding the administration of the decedent’s estate.

Florida Homestead Protection 101 – what to know

October 9, 2020 | by Chepenik Trushin LLP

Homestead Protection: Can You Lose It in Probate?

A person’s home (homestead) is often the most important asset in their estate plan because of the monetary and sentimental value that is inherent in a person’s main residence. Florida has special rules that govern a person’s primary residence, known as homestead property. Unless a creditor is the IRS, a mortgagee, or a laborer that performed work on the home, a homestead property is safe from creditors’ claims. Essentially, the homestead is exempt from a forced sale of the property unless there is a special creditor.

To qualify for homestead protection, a person must be a permanent resident of Florida, and the homestead must be that person’s primary place of residence, among other rules. This means that second homes and investment properties are ineligible for such protection. However, there is no monetary cap associated with the exemption, so a Florida resident that invests millions of dollars into their primary residence will receive full protection.

In Florida, if you are going through a Divorce or Family Collaborative law process, ensure to include your Estate planning and Beneficiaries

July 9, 2020 | by Chepenik Trushin LLP

What Happens to My Estate Plan When I Divorce?

People often designate their spouse as a primary beneficiary in their will, trust, or beneficiary designation, but what happens in the case of divorce? Oftentimes, a person may neglect to update their testamentary plan following a divorce and leave their ex-spouse as a beneficiary. Thankfully, in Florida, several laws help automatically update a person’s estate plan upon divorce to avoid unintentionally bequeathing a gift to an ex-spouse.

Florida law provides that any provision of a will in favor of a divorced spouse treats that former spouse as if that spouse had already died. The controlling statute, Fla. Stat. § 732.507(2) states the following:

Lack of Testamentary capacity and undue influence – what are the legal standards?

December 23, 2019 | by Chepenik Trushin LLP

How Can you Prove Undue Influence?

For a Will to be valid, certain conditions must be met. The testator must have legal capacity, at least eighteen years old, must have testamentary intent, and the will must not be a product of undue influence or duress. The first two requirements are usually relatively easy issues to resolve, but undue influence and duress is not always clear. As the Supreme Court of Florida explained, “[u]ndue influence is not usually exercised openly in the presence of others, so that it may be directly proved, hence it may be proved by indirect evidence of facts and circumstances from which it may be inferred.”

In In re Estate of Carpenter, the Supreme Court of Florida listed a set of seven, non-exhaustive factors to consider when deciding cases of Undue Influence:

Four important reasons to update your estate plan and/or your trust documents

December 2, 2019 | by Chepenik Trushin LLP

I Already Have a Will; When Should I Update My Estate Planning Documents?

When someone executes a valid will, some people assume that if their wishes do not change, they should never have to revisit their estate plan. However, there are certain common events in life that should cause you to review or update your estate planning documents.

Marriage/Divorce: A surviving spouse is entitled to a percentage of a decedent’s estate, regardless of whether the decedent included the spouse in the decedent’s will. Interestingly, the amount that a surviving spouse is entitled to may vary depending on whether the will was executed before or after the marriage. If you execute a will and subsequently marry, the spouse will receive a share equal to what he or she would have had, had the testator died intestate. This typically amounts to either one-half of the estate (if there are children of the decedent who are not children of the surviving spouse), or the entire estate (if there are no surviving children, or if the surviving spouse and the decedent are the parents of the only surviving children). Fla. Stat, Sec. 732.301 and Sec. 732.102. In either case, this is more than the amount that a surviving spouse is entitled to under the “elective share” which is thirty percent (30%) of the decedent’s estate.

Beneficiaries of a Florida based trust – know the law, especially if you don’t live in Florida

August 16, 2019 | by Chepenik Trushin LLP

The Long Arm of the Law – Trust Litigation and Out-of-State Beneficiaries

When dealing with trusts, there is a possibility that the potential litigation or present lawsuit involves people from multiple jurisdictions and multiple states. A trust may be created and administered in Florida, but the beneficiaries may live elsewhere. If this is the case, can the beneficiaries still be sued in Florida?

The Southern District of Florida discussed the issue of personal jurisdiction over a party when dealing with an in-state trust and an out of state beneficiary in Abromats v. Abromats. Gloria Abromats, executed a revocable trust while she was residing in Florida. Further amendments were made to Trust, which one of her sons, Clifford, claimed were procured through undue influence over Gloria by his brother Phillip. Phillip lived in Wyoming and received distributions from the trust. Clifford filed suit against Phillip in Florida, but Phillip argued that the court did not have jurisdiction over him in Florida.