Legacy Under Threat? A Guide to Handling Contested Wills in Central Florida

April 10, 2025
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Planning For Life...Building For Legacy. At Sibley Law & Associates, PLLC, this isn't just a tagline; it's the core principle guiding our work with families throughout Central Florida. We help individuals meticulously plan their estates to ensure their wishes are honored and their legacy is secure. However, even with the best intentions, the period following the loss of a loved one can sometimes become fraught with unexpected challenges. One of the most difficult situations that can arise is a will contest – a legal dispute challenging the validity of the deceased person's final wishes.


The discovery of a will often brings a sense of closure, outlining the final intentions of someone dear. But what happens when a family member, heir, or beneficiary believes that the document doesn't truly reflect the deceased's wishes, or that it was created under improper circumstances? This is where the complex and emotionally charged process of contesting a will begins.


Navigating a will contest requires not only a deep understanding of Florida probate law but also sensitivity, strategic thinking, and robust advocacy. This is where experience matters immensely. Attorney Dee Sibley, the Founding Attorney of Sibley Law & Associates, PLLC, is recognized as one of Central Florida's most experienced and trusted estate planning attorneys. With years spent both helping clients proactively plan their estates to minimize conflict and representing clients in probate litigation when disputes arise, Dee Sibley brings invaluable perspective and skill to these challenging situations.


This guide aims to shed light on the process of handling contested wills in Central Florida, explaining the grounds for such challenges, the typical procedures involved, and the critical importance of experienced legal counsel.


What Exactly is a Will Contest?

A will contest isn't simply a disagreement over how to interpret a clause in a will. It's a formal lawsuit filed in probate court that challenges the legal validity of the entire will document, or specific parts of it. The person initiating the contest (the petitioner) essentially argues that the will presented for probate should not be considered the true, legally binding last testament of the deceased (the decedent).


Under Florida law, only "interested persons" have the legal standing to contest a will. An interested person is typically someone who stands to gain financially if the will is invalidated or someone who would have inherited under a previous valid will or through Florida's intestacy laws (the laws governing inheritance when there is no valid will). This usually includes spouses, children, beneficiaries named in the current or a prior will, and heirs-at-law.


Common Grounds for Contesting a Will in Florida

A will contest cannot be based simply on disappointment or a feeling that the distribution is unfair. Florida law requires specific legal grounds to successfully challenge a will's validity. Dee Sibley and the team at Sibley Law & Associates have extensive experience navigating contests based on the following common grounds:


  1. Improper Execution (Lack of Formalities): Florida has very strict requirements for how a will must be signed and witnessed to be valid (outlined in Florida Statutes Section 732.502). These include:
  2. The will must be in writing.
  3. The testator (the person making the will) must sign it at the end, or another person must sign at the testator’s direction and in their presence.
  4. The testator's signing (or acknowledgment of their signature) must occur in the presence of at least two attesting witnesses.
  5. The witnesses must sign the will in the presence of the testator and each other. Failure to comply precisely with these formalities can render the entire will invalid. 
  6. Lack of Testamentary Capacity: This ground alleges that the testator did not possess the required mental capacity at the time the will was signed. Under Florida law, testamentary capacity means the testator generally understood:
  7. The nature and extent of their property.
  8. The natural objects of their bounty (i.e., who their family members and loved ones were).
  9. The practical effect of the will they were signing (i.e., how it would distribute their property). Challenges often involve demonstrating conditions like dementia, Alzheimer's disease, severe illness, or the influence of medication impaired the testator's understanding at the crucial moment of execution. Medical records and witness testimony are key evidence here.
  10. Undue Influence: This is one of the most common grounds for will contests. Undue influence occurs when someone exerts such significant pressure or control over the testator that it overcomes the testator's free will, essentially substituting their own desires for the testator's intentions in the will. To prove undue influence in Florida, one typically needs to show:
  11. The alleged influencer maintained a confidential relationship with the testator.
  12. The alleged influencer was actively involved in procuring the will (e.g., arranging the attorney, being present at signing, isolating the testator).
  13. The alleged influencer is a substantial beneficiary under the will. If these factors are established, the burden often shifts to the proponent of the will to prove its validity.
  14. Fraud: Fraud occurs if the testator was intentionally misled into signing the will or including certain provisions based on false information. This could involve:
  15. Fraud in the Execution: The testator was deceived about the nature of the document they were signing (e.g., told it was something other than a will).
  16. Fraud in the Inducement: The testator signed the will based on misrepresentations made by someone who benefits from those lies (e.g., falsely telling the testator negative things about another family member to get them disinherited).
  17. Duress: While similar to undue influence, duress involves coercion through threats or actual harm, forcing the testator to sign the will against their true wishes.
  18. Mistake: Generally, a mistake in the inducement (the testator based their decision on an erroneous belief not caused by fraud) is not grounds to invalidate a will. However, a "mistake in the factum" (a mistake about the actual contents of the will or the nature of the document being signed) might be grounds for challenge under specific, limited circumstances.
  19. Revocation: A will contest might argue that the presented will is invalid because it was previously revoked by the testator. Revocation can occur by executing a later valid will or codicil (an amendment), or by a physical act (like burning, tearing, or destroying the will) coupled with the intent to revoke.

The Will Contest Process in Central Florida: Navigating Probate Litigation

A will contest is a form of probate litigation – a lawsuit conducted within the framework of the county probate court (e.g., Orange, Seminole, Osceola County Circuit Courts for Central Florida). The process generally involves these stages:


  • Strict Deadlines: Florida law imposes tight deadlines for filing a will contest. Generally, an interested person must file a petition challenging the will before the court admits the will to probate or within a specific timeframe after formal notice of the probate proceedings has been served – often as short as 20 days, or 90 days from the Notice of Administration for others. Missing these deadlines typically bars the challenge permanently. Acting quickly is paramount.
  • Filing the Petition: The contestant files a formal petition with the probate court outlining the grounds for challenging the will's validity and the relief sought.
  • Discovery: Like other lawsuits, this phase involves gathering evidence. Attorneys use tools like depositions (sworn testimony), interrogatories (written questions), requests for production of documents (medical records, financial statements, attorney notes), and subpoenas to build their case.
  • Motions and Hearings: Attorneys file various legal motions (e.g., motions to dismiss, motions for summary judgment) and argue them before the probate judge.
  • Mediation/Settlement: Courts often encourage or require parties to attempt mediation – a confidential process where a neutral third party helps facilitate settlement negotiations. Many will contests are resolved through settlement agreements to avoid the cost, stress, and uncertainty of a trial.
  • Trial: If settlement fails, the case proceeds to trial. In Florida, will contests are typically tried before a judge, not a jury. Both sides present evidence, examine witnesses, and make legal arguments.
  • Judgment and Appeals: The judge issues a ruling either upholding the will or declaring it invalid (in whole or in part). If the will is invalidated, the court may admit a prior valid will to probate or declare an intestacy (meaning assets pass according to state law as if there were no will). The losing party may have grounds to appeal the decision.


How to Handle a Will Contest: Practical Steps

Whether you are considering challenging a will or find yourself needing to defend one, the stakes are high, both financially and emotionally.


If You Are Considering Contesting a Will:

  1. Act Immediately: Due to the strict deadlines, consult with an experienced probate litigation attorney as soon as possible.
  2. Gather Information: Collect any documents, emails, notes, or names of potential witnesses that support your belief that the will is invalid.
  3. Seek Experienced Counsel: Contact a firm like Sibley Law & Associates. Attorney Dee Sibley can evaluate the potential grounds for your challenge, explain the legal process, assess the strength of your case, and discuss the potential costs and benefits of proceeding. Not every suspicion warrants a full contest.


If You Are Defending a Will (as Personal Representative or Beneficiary):

  1. Take the Challenge Seriously: Do not ignore any formal notice or petition contesting the will.
  2. Hire Experienced Probate Litigation Counsel: The Personal Representative (executor) generally has a duty to defend the will in good faith. Beneficiaries whose inheritance is threatened also need representation. Dee Sibley’s experience is crucial for mounting a strong defense.
  3. Understand the Allegations: Work with your attorney to understand the specific grounds being alleged by the contestant.
  4. Cooperate Fully: Provide your attorney with all requested information and documentation to help build the defense strategy.


The Indispensable Role of Experienced Counsel: Why Dee Sibley?

Will contests are not simple legal matters. They involve complex procedural rules, specific evidentiary standards, and require skillful navigation of both legal precedent and often intense family dynamics. Attempting to handle a will contest without experienced legal representation is highly inadvisable.


Dee Sibley and Sibley Law & Associates, PLLC offer:

  • Proven Experience: Decades of combined experience specifically in Florida estate planning and probate litigation, providing a comprehensive understanding from both proactive planning and dispute resolution perspectives.
  • In-Depth Knowledge: Mastery of Florida probate code, rules of evidence, and local Central Florida court procedures.
  • Strategic Advocacy: Skill in developing effective case strategies, whether pursuing a contest or defending a will's validity.
  • Negotiation & Litigation Skills: Ability to negotiate favourable settlements when possible and vigorously litigate in court when necessary.
  • Client-Centered Approach: Understanding the emotional toll these disputes take, providing compassionate guidance alongside strong legal representation.
  • Local Trust: A recognized and respected presence in the Central Florida legal community.


Our firm’s commitment, "Planning For Life...Building For Legacy," extends to protecting that legacy when it comes under fire. Sometimes, building and preserving a legacy requires defending it in court.


Preventing Contests Through Proactive Planning

While not the focus of this post, it's worth noting that the best way to handle a will contest is to prevent one from happening in the first place. Working with a knowledgeable estate planning attorney like Dee Sibley to create your will can significantly minimize the risk of future challenges by ensuring all legal formalities are met, addressing potential capacity concerns proactively, and carefully documenting your intentions to thwart potential claims of undue influence or fraud.


Protecting Your Rights and Honoring Legacy

Will contests are among the most challenging legal disputes families can face, arising during a time already marked by grief. Whether you suspect a loved one's will is invalid or you are tasked with defending a will against a challenge, navigating the Central Florida probate court system requires diligence, expertise, and immediate action.


Don't face this complex process alone. If you are involved in or anticipating a will contest in Central Florida, trust the experience and dedication of Sibley Law & Associates, PLLC. Contact Attorney Dee Sibley today for a consultation to understand your rights, explore your options, and receive the skilled legal guidance necessary to protect your interests and honor the true legacy of your loved one.


Disclaimer: This blog post is intended for informational purposes only and does not constitute legal advice or create an attorney-client relationship. Will contest laws and probate procedures are complex and fact-specific. You should consult with a qualified Florida probate litigation attorney regarding your particular situation. Contact Sibley Law & Associates, PLLC for personalized legal counsel tailored to your needs.

June 6, 2025
Life in Melbourne, Florida, is something special. We live where others vacation, enjoying the unique rhythm of the Space Coast, the beautiful beaches, and the vibrant community we call home. We meticulously plan for so many aspects of our lives here—from hurricane season and family vacations to retirement and our children’s education. Yet, one of the most crucial forms of planning is often overlooked: estate planning. Many Melbourne residents believe estate planning is a tool reserved for the ultra-wealthy or something to consider only in their golden years. This is a dangerous misconception. The reality is, if you are an adult with assets or loved ones who depend on you, you need an estate plan. It is the ultimate act of protection for your family and the foundation for your legacy. Without a comprehensive estate plan, you are leaving the most critical decisions about your assets, your health, and even your children's future up to the state of Florida and the Brevard County courts. At Sibley Law & Associates, PLLC, we believe every Melbourne family deserves the peace of mind that comes from taking control. This is what "Planning For Life...Building For Legacy" truly means. Let’s explore why this planning is so essential for your family. When You Don’t Make a Plan, Florida Makes One for You One of the most significant consequences of not having a Last Will and Testament is that you die "intestate." This legal term means the state of Florida, through its rigid intestacy statutes, will dictate exactly how your assets are distributed. This pre-set formula does not consider your personal wishes, the nuances of your relationships, or your family’s specific needs. How Florida’s Intestacy Laws Work: The state’s plan is based entirely on familial relationships. Here are a few common scenarios for Melbourne residents: Married with Shared Children: If you are married and all your children are descendants of both you and your surviving spouse, your spouse will inherit your entire estate. This may sound fine, but what if you wanted to set aside specific assets for your children immediately? Without a plan, you have no say. Married with Children from a Prior Relationship: This is where Florida's plan can be particularly surprising. If you have children from a previous relationship, your surviving spouse inherits only half of your estate. The other half is divided among all of your children (from both your current and prior relationships). This could create unintended financial strain on your spouse and potential conflict within your blended family. Single with Children: Your children inherit your entire estate, divided equally. Married with No Children: Your surviving spouse inherits everything. Single with No Children: Your estate will pass to your parents. If they are deceased, it goes to your siblings, and the line of succession continues down a prescribed path. Who Gets Left Out? Florida's intestacy laws make no provisions for unmarried partners, regardless of how long and committed the relationship. A beloved significant other, a cherished friend who is like family, or a favorite charity will receive nothing from your probate estate without being explicitly named in a Will or Trust. Effective estate planning ensures that the people and causes you care about most are the ones who benefit from your life's work. Protecting Your Most Precious Assets: Your Children For any parent in Melbourne, there is no greater concern than the well-being of their children. A comprehensive estate plan is the single most important tool you have to protect them if you are no longer there to do so yourself. The Critical Role of Naming a Guardian If you have minor children and pass away without legally nominating a guardian, the 18th Judicial Circuit Court in Brevard County will be forced to appoint someone to raise them. A judge, acting with the best intentions but without knowing you or your family, will make this life-altering decision. This process can be fraught with problems: Uncertainty and Instability: While the court deliberates, your children could be placed in temporary care, adding trauma to an already devastating situation. Family Disputes: Well-meaning relatives might disagree on who is best suited to be the guardian, leading to public and painful court battles that can permanently damage family relationships. An Unintended Choice: The judge may appoint someone you would never have chosen—someone with different parenting philosophies, religious beliefs, or financial habits. Your Last Will and Testament is the only legal document where you can nominate the guardians you want for your children. This is your voice, telling the court who you trust to provide the love, care, and stability your children deserve. You can also name alternate guardians in case your first choice is unable to serve. This single act provides immense clarity and protection. Managing Your Children’s Inheritance Leaving a large inheritance directly to an 18-year-old is rarely advisable. Without planning, that is exactly what could happen. A well-designed estate plan can establish a Trust for your children. This allows you to appoint a Trustee—a trusted person or financial institution—to manage the inheritance on their behalf. You can set the terms for distribution, ensuring the funds are used for important milestones like education, a first home purchase, or starting a business, and distributed at ages when they are mature enough to handle the responsibility. Planning for Life's "What Ifs": The Importance of Incapacity Planning Estate planning isn't just about what happens after you die. It's equally about protecting yourself and your family if you become incapacitated and unable to make decisions for yourself due to an accident or illness. Without proactive incapacity planning, your family may face what is often called a "living probate." The Alternative to Planning: Court-Ordered Guardianship If you become incapacitated without a plan, your loved ones would have to petition the Brevard County court to have you declared legally incompetent and have a guardian appointed. This process can be: Public: Your private medical and financial details become part of the public record. Expensive: It involves significant attorney's fees and court costs, all paid from your assets. Time-Consuming: The legal process can be slow and cumbersome. Stressful: It places a tremendous emotional burden on your family during an already difficult time. The Solution: Essential Incapacity Documents A comprehensive Melbourne estate plan includes critical documents to avoid this scenario: Durable Power of Attorney: This document allows you to appoint a trusted agent to manage your financial and legal affairs if you are unable to do so. This person can pay bills, manage investments, and handle property matters on your behalf without court intervention. Health Care Surrogate Designation: This lets you name a person to make medical decisions for you if you cannot communicate your own wishes. This ensures decisions are made by someone who knows you and your values. Living Will: This document outlines your wishes regarding life-prolonging medical procedures, providing clear guidance to your family and doctors and relieving them of the burden of making these difficult decisions on their own. Navigating the Brevard County Probate Process Probate is the formal court-supervised process of validating a Will, paying off estate debts, and distributing assets to beneficiaries. In Florida, even if you have a Will, your estate will likely go through some form of probate. However, a well-drafted estate plan can make this process significantly smoother and more efficient. Without a plan, the probate process can become more complex and contentious, as the court must first identify legal heirs and appoint a Personal Representative. With a properly drafted Will, you choose your Personal Representative (Executor), streamlining the initial stages. The Power of Trusts to Avoid Probate For many Melbourne families, a primary goal of estate planning is to avoid probate altogether. This is most commonly achieved through a Revocable Living Trust . Assets titled in the name of your Trust during your lifetime do not have to go through the probate process upon your death. They can be managed and distributed privately by your chosen successor Trustee. This offers several key benefits: Privacy: Trusts are not public documents like Wills. Efficiency: Trust administration is typically much faster than probate, allowing assets to be distributed to your loved ones more quickly. Cost Savings: By avoiding court fees and minimizing legal expenses, more of your estate is preserved for your beneficiaries. Continuity: A Trust also provides for seamless management of your assets if you become incapacitated, as your successor Trustee can step in immediately without court involvement. Your Melbourne Family Isn't Cookie-Cutter; Your Plan Shouldn't Be Either Every family in Melbourne is unique, and a one-size-fits-all approach to estate planning is ineffective. A knowledgeable attorney can tailor a plan to your specific needs: Young Families: The focus is often on nominating guardians and establishing trusts for minor children. Blended Families: Planning is critical to clearly define how assets are distributed between a current spouse and children from a previous relationship, preventing disputes. Business Owners: A plan must integrate business succession strategies to ensure the company you built can continue to thrive. Retirees: The focus may shift to asset preservation, legacy planning for grandchildren, charitable giving, and planning for long-term care. Your Legacy is a Choice—Make It a Deliberate One Estate planning is one of the most profound acts of love and responsibility you can undertake for your family. It replaces uncertainty with clarity, chaos with order, and court control with your control. It ensures that your life's work creates a lasting, positive legacy for the people you care about most. Don't leave your family’s future in Melbourne to chance. Take the First Step Today Creating a comprehensive estate plan is a straightforward process when guided by an experienced professional. If you are ready to secure your family’s future and build your legacy with intention, we invite you to take the next step. Book Your Consultation Today . Contact a knowledgeable Melbourne, Florida estate planning attorney at Sibley Law & Associates, PLLC to begin designing a plan that provides true peace of mind for you and your loved ones. This article is a service of Sibley Law & Associates , a Personal Family Lawyer® Firm . We don’t just draft documents; we ensure you make informed and empowered decisions about life and death, for yourself and the people you love. That's why we offer a Life & Legacy Planning Session™, during which you will get more financially organized than you’ve ever been before and make all the best choices for the people you love. You can begin by calling our office today to schedule a Life & Legacy Planning Session™. This material was created for educational and informational purposes only and is not intended as ERISA, tax, legal, or investment advice. If you are seeking legal advice specific to your needs, such advice services must be obtained on your own separate from this educational material.
June 4, 2025
Photo by Malone & Company Photography. "Tony Hsieh." May 24, 2010. www.flickr.com/photos/siliconprairienews/4636417133 Imagine this: you build an empire worth hundreds of millions, transform a city, and leave behind a legacy of innovation and generosity—only to have your loved ones spend years trapped in legal battles because your estate plan was missing, outdated, or misunderstood. This isn’t fiction. It’s the real story of Tony Hsieh, former CEO of Zappos, who died unexpectedly in 2020 at just 46. For years, it was believed he had no will. Then—nearly five years later—a mysterious document surfaced. And just like that, everything changed. But the damage was already done. A Legacy Lost in Limbo Tony Hsieh’s fortune, once valued at over $500 million, has been tied up in legal fees, creditor claims, and emotional turmoil for his family and business partners. The recently discovered will, dated 2015, was found not by a lawyer or family member, but in the possession of a man suffering from Alzheimer’s who had recently passed away himself. The will allegedly includes: A no-contest clause threatening to disinherit family members if they challenge it Confusing instructions Unknown executors, including someone close friends say they’ve never heard of Even if this document is deemed legally valid, it may raise more questions than answers. It also raises a critical truth: Without proper estate planning—no matter your age or net worth—your legacy can unravel fast. Why Traditional Estate Planning Falls Short At Sibley Law & Associates, we often see how traditional estate planning fails families. A will alone, even when properly signed and notarized, is not a plan. It's a document. And documents, especially if they're hidden, outdated, or incomplete, can create more conflict than clarity. Here’s what often goes wrong with traditional estate planning: The plan exists only in documents, not in conversations or relationships. The will is not stored securely or is forgotten altogether. There’s no clear guidance for what loved ones should do when the unthinkable happens. There’s no connection between the documents and a complete asset inventory. There’s no system in place to update the plan as life, relationships, and assets change. These gaps are what allow confusion and conflict to creep in—just like they did in Hsieh’s case. The Cost of an Incomplete Plan Tony Hsieh’s family has spent five years managing uncertainty, litigation, and pressure—all while grieving a tragic loss. His businesses, properties, and philanthropic intentions have been caught in limbo. What should have been a well-protected legacy has instead become a cautionary tale. Here at Sibley Law, we ask every client: If something happened to you tomorrow… would your loved ones know what to do? Would they know who to call? Would they be protected from unnecessary stress, court battles, or infighting? Why Life & Legacy Planning® Is Different We don’t believe in one-size-fits-all documents. We believe in relationships, updates, and real clarity . That’s what our Life & Legacy Planning® process is designed to provide. When you work with us, you’re not just getting a will or trust. You’re creating a living, evolving plan that includes: A complete inventory of your assets—so nothing gets lost or overlooked Instructions on where to find your plan and who to contact Ongoing updates to keep your plan aligned with your life Guidance for the people you’ve named—so they’re not left wondering what to do A relationship with your Personal Family Lawyer®—so your family has a trusted guide A chance to share not just your assets, but your values and stories with future generations This is how we keep families out of court and out of conflict—no matter what. Planning for Life. Building for Legacy. At Sibley Law, our mission is clear: to help Florida families create strong, legally sound plans that protect what matters most. We believe that legacy isn’t just about wealth. It’s about clarity, continuity, and care. Let Tony Hsieh’s story serve as a powerful reminder: It’s not enough to write a will. You need a plan. And your plan needs to be living, reviewed, and connected to the people you love. This article is a service of Sibley Law & Associates , a Personal Family Lawyer® Firm . We don’t just draft documents; we ensure you make informed and empowered decisions about life and death, for yourself and the people you love. That's why we offer a Life & Legacy Planning Session™, during which you will get more financially organized than you’ve ever been before and make all the best choices for the people you love. You can begin by calling our office today to schedule a Life & Legacy Planning Session™. This material was created for educational and informational purposes only and is not intended as ERISA, tax, legal, or investment advice. If you are seeking legal advice specific to your needs, such advice services must be obtained on your own separate from this educational material.
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