Paul O. Dillon, Attorney at Law

Can You Prevent a Will from Being Contested?

A 65-year-old woman wishes to have her estate organized by an executor, with the request that 90% of her assets be left to one of her grandchildren. She asks how she can be sure the executor will decide how to distribute her assets when the grandchild is 25 years old. To add a twist, there are several other grandchildren.

This situation, described in an article, “’ The situation is extreme’: I’m 65 and leaving my estate to only one grandchild. Can the others contest my will?” from MarketWatch, reveals the dangers of not understanding estate planning basics.

The executor has nothing to do with when or how to distribute assets to heirs. Their role is to follow the directions in the will, which should be expressed by the testator, or the person creating the will.

In cases like this, a will should be created by an experienced estate planning attorney. It should include the names of all individuals included in the distribution and those who should be excluded. An estate planning attorney may advise this person to create a trust, with a trustee to carry out their instructions, in addition to the will. The terms of the trust must be crystal clear, so that no one can challenge the trust, and the same applies to the will.

How to do this? While you can’t prevent someone from challenging a will, and an executor can’t take on the role of enforcer, an experienced estate planning attorney will know how to create an estate plan to withstand challenges.

First, make sure the will and trust are created when you are healthy, and of “sound mind and body.” Once someone starts displaying signs of dementia, it is easier to challenge a will or trust and claim the person wasn’t competent to make decisions. The trust and estate attorney will also know the law in your jurisdiction about creating and finalizing these documents. In some states, you only need one witness to finalize a will, while in others, you need two people. This is a minor detail. However, it can render an estate planning document invalid.

There is also a clause used in some states known as the in terrorem clause. Any beneficiary who contests the will automatically forfeits their right to inherit anything from the estate. This clause is used (where permitted) when a will challenge is expected. If this is allowed in your state, your estate planning attorney will know how to incorporate it into your will.

A common reason for wills and trusts to be deemed invalid might surprise you. People often neglect to put their final signature on a will or trust. A will could be entirely correct and well prepared. However, if it’s not signed, it’s not valid.

There are also trusts specifically created for individuals with disabilities, known as Special Needs Trusts. They are designed to benefit heirs who may not be able to manage an inheritance or who receive means-tested government benefits and may not own more than a certain amount of assets. Special Needs Trusts are also used by families who have a member with a substance abuse issue.

The best advice for this grandmother, who favors one grandchild, is to meet with an experienced estate planning attorney to discuss the situation candidly and outline her goals. She must make the decisions about how her estate is to be distributed and put them down on paper, so the executor can follow her directions.

Reference: MarketWatch (May 30, 2025) “’The situation is extreme’: I’m 65 and leaving my estate to only one grandchild. Can the others contest my will?”

Celebrity Estate Planning Mistakes to Avoid

It’s hard to miss the major mistakes celebrities make—their lives and deaths are public and not always pretty. Expensive mistakes on a grand scale aren’t what most of us deal with, but there are good lessons to learn from their mistakes, says a recent article from Market Watch, “Sharon Stone’s missing $18 million, Prince’s estate back in court: what to learn from celebrity estate mistakes.”

Eight years after Prince’s death, his estate is back in court, while Sharon Stone was in the news when she revealed $18 million in savings disappeared while she suffered a life-threatening illness more than two decades ago. For conservatorship stories, while we aren’t hearing much about Britney Spears anymore, Jay Leno has filed for conservatorship for his wife Mavis, who has dementia, and musical legend Brian Wilson of the Beach Boys faced conservatorship issues when his caretaker wife died, and another caretaker had to be named.

We expect people with great professional success to be surrounded by a small army of trusted caretakers, estate planning attorneys, accountants, managers, and others. And we’d also expect them to want to keep as much of their lives private as possible. But as headlines show, people who are incredibly talented performers aren’t necessarily skilled in the legal and business aspects of their lives.

In 2001, Sharon Stone suffered a stroke. It took seven years for her to overcome the effects of the stroke, and she counted on others to manage her affairs. When she was finally able to start taking control of her life, she found everything had been put into someone else’s name, and $18 million was missing from her bank account.

While she’s not forthcoming with details, this was likely a trusted person abusing their role as Power of Attorney, where a fiduciary was appointed without enough oversight. For regular people, an estate planning attorney could create a plan where, in addition to a Power of Attorney for certain accounts, like running the household, more considerable assets are placed in a trust, and the trustee is not the same person as the POA. Checks and balances need to be built into an estate plan to protect individuals in case of incapacity.

In cases where the fiduciary has performed poorly, and a family member challenges the results, the results are common. When the court reviews the matter, changes can be made to appoint another person to the POA. Courts can also step in to take over another person’s finances, but it usually doesn’t happen until after significant damage has been done.

A meeting with an estate planning attorney should include discussions about who is qualified to serve as a Power of Attorney and how their actions may be reviewed. In many instances, trust is not the issue, but competence is. Are they capable of managing the affairs of an incapacitated person? If not, another person should be selected, regardless of whose feelings might be hurt by the decision.

Reference: Market Watch (July 13, 2024) “Sharon Stone’s missing $18 million, Prince’s estate back in court: what to learn from celebrity estate mistakes”

Why Do Older People Hide Money in Their Homes?

While this may sound absurd to a cash-free generation, some still take comfort in having stashes of paper money at home. We know one daughter whose mother kept rolls of bills in the freezer and another whose father kept a shoebox of $100 bills in the attic. If the person is known to be a bit eccentric, it may be amusing. However, it is only until the family realizes the difficulties this behavior may present.

For heirs finding these stashes while cleaning out the family home—or mistakenly tossing them—hidden cash inheritances can present a number of problems. A recent article from The New York Times, “When the Money Is Under the Mattress. Or in the Freezer. Or a Shoebox,” explains how this old-school savings plan can go sideways.

Large sums of money thrown in the trash are just one risk. If others learn about the cash stash, having so much cash on hand could lead to the home being broken into. If there’s a fire or flood, the money could be destroyed.

There are more risks: if siblings dispute their parents’ estate plan, a more aggressive person might take the money without telling anyone. If an adult child is the main caretaker while others live far away, there will always be some suspicion. Did they take some cash before sharing the rest with their siblings?

Placing substantial amounts of cash into a savings account can take advantage of the power of compounding interest, which is especially valuable over decades. The only thing cash hidden in a closet will gather is dust.

A cache of cash creates accounting and tax problems as well. There’s no ownership record for cash, so it’s impossible to determine who it belongs to. This can be especially problematic for families whose estates are close to the threshold of the federal or state estate or inheritance taxes. How do you account for $500,000 in cash and gold bars hidden in the home? This happened to an estate planning attorney interviewed for the article.

Cash hoarding can be a result of dementia and Alzheimer’s disease, which can cause paranoia. This makes people feel they need to hide valuables and cash to protect them.

Estate planning attorneys often recommend establishing trusts and taking other steps as soon as possible when adult children notice their parents' diminished capacity. A Power of Attorney and revocable trust could allow the child to manage the parents' finances.

On a practical level, preparing an estate plan and conducting a thorough inventory of all assets, including cash and valuables in the home, makes life easier for heirs. Focusing on finding hidden treasures while grieving the loss of a family member creates a complication for the family and may tarnish a legacy.

Reference: The New York Times (June 8, 2024) “When the Money Is Under the Mattress. Or in the Freezer. Or a Shoebox.”

How Do I Create End-of-Life Plan?

Any family facing the end-of-life of a loved one deserves to know what their loved ones want, as observed in an article from The New York Times, “How to Make End-of-Life Planning Less Stressful.” Hosting a family gathering with pizza and chocolate cake made the conversation easier for one family.

The reporter learned things about her family she never knew. Her parents didn’t want a memorial service because, as they told her, they don’t like big gatherings, alive or dead. A sister wants her memorial service held at Starbucks. The discussion included the possibility of having cremated remains pressed into a vinyl record of the person’s choice (her father’s comment). Taking a lighter approach worked for this family.

Here are some suggestions to start this important, albeit difficult, conversation:

First, ask the family members involved if they’d be open to a family meeting and set a date. It could be done via Zoom, although in-person is better if they are far-flung.

You could bring up a news story about dementia and say it got you thinking about how important it is to talk about these issues now. If you are the older family member, tell your loved ones you are putting your affairs in order and want to spare them the added stress of figuring out your healthcare and funeral wishes.

Create a document for the family to review and a checklist of topics and prompts to review. Two key areas to discuss are deciding who will serve as your health care proxy if you cannot make health care decisions and what directives you want in a living will.

Once these are decided, your estate planning attorney can make it enforceable by preparing a Durable Power of Attorney for Health Care. Copies should be given to loved ones and your doctor.

Another topic to cover, often overlooked, is what you or your aging parents want to do with the remaining years. You might ask, “What is undone in your life?” You may learn your parents have always wanted to visit an ancestral village in Italy or travel to see the Northern Lights. How can you help them make this happen? If your aging parent is a widow or widower, could an adult child travel with them?

These are significant questions and can’t always be resolved in one meeting. Having “check-in” conversations throughout the year will foster further communication between family members. This may also expand to issues like ensuring that their home is accessible for aging, from a ramp for the front steps to properly installed grab bars in the shower.

The conversation should also address the creation of a last will and testament. If your aging parents don’t have a will and you do, share your estate planning attorney’s contact information. If none of you has an estate plan in place, these conversations could help all the family move this critical task to the forefront.

Reference: The New York Times (March 8, 2024) “How to Make End-of-Life Planning Less Stressful”

How to Get a Conservatorship for a Parent

One woman felt she had no choice but to retain an attorney and petition the court for a conservatorship to manage her father’s finances. Her father had been targeted by a family acquaintance who tried to isolate him from his family. The acquaintance then married the widower and promptly took over his bank accounts. She was also appointed as the trustee of his revocable trust, as explained in an article from The Atlanta Journal-Constitution, “When it’s the right time to pursue conservatorship for your loved one.”

Conservatorship concerns the financial affairs of a person, managing assets and handling financial decisions for someone who cannot do so for themselves, whether from illness, injury, or other types of incapacity. A guardian is more concerned with the well-being and personal care of an incapacitated individual or minor, including day-to-day decision-making and healthcare decisions.

For the family situation mentioned above, the daughter researched ways to protect her father from losing everything. All resources pointed to conservatorship as the solution. The family was able to protect the father’s assets, including the nearly $200,000 eventually needed to provide round-the-clock medical care during his final year of life.

One daughter served as legal guardian, while a third-party county conservator managed financial matters. The pressure was relieved from the woman and her siblings by deferring the money management to a professional. Having a neutral third party handle finances allows the siblings to focus on their father’s care.

A conservatorship or guardianship is court-supervised and established when a person is deemed incompetent. By contrast, a Power of Attorney is a voluntary arrangement made while the person is still competent, offering a less intrusive alternative without court involvement.

In some situations, even when a Power of Attorney is in place, a court-appointed guardianship or conservatorship becomes necessary.

A conservatorship may become necessary because of significant mental decline from diseases like Alzheimer’s or a person’s inability to manage their personal or financial affairs. Anyone considering a conservatorship for a loved one must speak with an estate planning attorney. The attorney should have experience in probate courts, estate law, conservatorship and guardianship law and an empathic understanding of family dynamics.

People are advised to create estate plans as soon as possible, including executing an advance directive for health care and a durable power of attorney. If they lose their mental capacity without having executed a will, they leave themselves vulnerable to elder financial abuse.

Reference: The Atlanta Journal-Constitution (March 1, 2024) “When it’s the right time to pursue conservatorship for your loved one”

How to Protect Your Spouse when Diagnosis Is Dementia

Few illnesses are as terrifying as dementia, for which there is no cure. If estate planning is in place, it may need to be adjusted to address new, more imminent issues. Reviewing the family situation from a legal and financial aspect is critical, and there is no time for delay, explains a recent article from Morningstar, “’I don’t want my wife to lose everything’: I’ve been diagnosed with dementia –I suddenly could not spell or write legibly.”

There are a number of steps to be taken to smooth the path ahead. First is to update your will and create a financial power of attorney. Don’t try to do this without the help of an experienced estate planning attorney.

This may also be the time to reassess your investment portfolio based on your new financial plan and risk tolerance.

An Advanced Healthcare Directive will inform doctors what actions you want them to take when you cannot make those decisions for yourself. You may want to list your wife as your healthcare proxy to carry out these decisions, but be mindful of the pressures put on a marriage when serious healthcare issues occur. Your spouse will need emotional support as well, and you’ll want to have a successor to your spouse for both the healthcare and POA documents.

Share your situation with trusted family and friends to create a team–a community of people who can provide support, part of which will be updating beneficiaries. Now would also be the time to record instructions for access to devices, documents, and even daily habits.

Long-term care insurance will help with expenses and should serve as an example for anyone reading this article. Policies should be purchased early in life when they are relatively affordable to help alleviate the financial burden of nursing home costs.

An estate planning attorney and financial advisor will help you take an accounting for assets, expenses, and projected long-term care costs. You’ll want a team approach to provide as much guidance as possible.

When to put your long-term care policies into payout status is a difficult decision. You’ll need to time this with a Medicaid plan, which your elder law estate planning attorney will be able to help with.

Now may also be the time to create a trust and divest assets to make it through the five-year Medicaid look-back, using your long-term care policy in the next five years.

There are exceptions to the five-year look-back rule for Medicaid eligibility. They include paying off debts, buying medical devices, or making home improvements to improve accessibility. However, eligibility depends upon income and other assets.

Some states, including Florida and New York, have rules exempting homes from assets calculated by Medicaid under certain circumstances. California eliminated an asset limit this year, making a person’s home automatically safe from Medicaid while they are living, but this does not mean it’s exempt from the Medicaid Estate Recovery Program.

Working with a team of professionals, including an estate planning attorney, and having the support of family and trusted friends will be important as time goes by and the disease progresses.

Reference: Morningstar (Feb. 25, 2024) “’I don’t want my wife to lose everything’: I’ve been diagnosed with dementia –I suddenly could not spell or write legibly”

Planning for Cognitive Decline Is Part of Estate Planning

Estate planning attorneys work to protect clients by creating advance medical directives, appointing a power of attorney and sorting through trust agreements, explains an article from Kiplinger, “Is Your Estate Ready if You Experience Cognitive Decline?”

Most consider estate planning a tool for distributing assets after death. However, it serves many purposes during life, including planning for cognitive decline and incapacity.

As we age, our cognitive abilities may start to decline, which needs to be accounted for in investment portfolios. Many loved ones see this decline but aren’t comfortable speaking with family members about such a sensitive topic. Large financial institutions and skilled financial advisors have recognized this and created plans to prevent losses from poor decision-making. In addition to planning finances, meeting with an estate planning attorney and preparing for cognitive decline and incapacity is essential. Here are some of the topics to cover.

Appoint a Power of Attorney. This person will be responsible for making legal and financial decisions for you if you cannot. They need to be someone you trust implicitly with good fiscal skills.

Create a Living Will. It’s better to outline the medical treatment you’d want to receive if you cannot make these decisions while still competent. You can also designate someone else to make decisions on your behalf when you are incapacitated.

Discuss and plan for Long Term Care. What would your family need to do if you were diagnosed with Alzheimer’s disease or dementia and required care and supervision around the clock? Discuss living arrangements and finances to pay for care as part of your estate plan.

Create a plan for your estate. How will your wealth and assets be distributed after your death? Planning in advance saves your family from scrambling to figure out how you want your assets to be distributed, what bills need to be paid on your behalf to protect real estate property and what your wishes are for a funeral or memorial service.

These conversations are not easy or enjoyable. However, they are crucial to protecting yourself and your family from the unexpected and the inevitable. Making a plan for yourself and being prepared is the most you can do, and it’s also the only thing you can do. Talk with an experienced estate planning attorney to put your estate plan in place sooner rather than later.

Reference: Kiplinger (Feb. 7, 2024) “Is Your Estate Ready if You Experience Cognitive Decline?”

How Does Guardianship Work?

For family members of the estimated 6.5 million dementia patients in the U.S., it is crucial to understand whether guardianship may be an option for their loved one. A recent article from Next Avenue titled “Thinking of Becoming a Guardian?” explains how the guardianship process works and what factors go into the decision-making process.

Guardianship is the position of being responsible for someone else. State courts usually appoint a guardian to make decisions for a person, if the court finds that person to be incapacitated or unable to make safe and reasonable decisions for themselves. People who are placed under guardianship, known as “wards,” often lose their independence in making financial, legal and health care decisions.

If full guardianship is awarded, the person cannot make decisions about whether they may vote, marry, where they live, or make their own end-of-life decisions.

Two tasks that are evaluated when considering guardianship are a person’s ability to manage personal finances and to take medications as prescribed.

The court may call on a geriatrician or psychiatrist to evaluate the person’s functional behavior, cognitive function, disabling conditions and ability to meet their essential needs.

There are benefits to guardianship for someone who is not able to care for themselves. It ideally creates a safety net for a person who cannot make informed decisions for themselves.

this, of course, assumes that the guardian is honest and accountable, which is not always the case. The inconsistencies plaguing the guardianship system include minimum standards for guardians, lack of regular independent reviews of the need for guardianship and lack of educational requirements for guardians.

Once guardianship is assigned, there is a tendency for the person to become lost when no follow-up is done. The very same person who lacks capacity to care for themselves is not going to be able to advocate for themselves, contact an attorney or access funds for court proceedings.

There is also a tendency to assign full guardianship for a person, rather than less restrictive alternatives.

There are alternatives, but they require planning and discussion. More than 40% of Americans have not discussed their wishes for end-of-life care with their loved ones, according to an article in the Journal of the American Geriatrics Society. Families should have a conversation at the first sign of memory loss or when preparing for retirement regarding wishes for end-of-life care and write them down as part of an Advanced Directive—also known as a Living Will and Health Care Power of Attorney—when preparing their estate plan.

Another important document, although not legally binding, is a “Value History,” where you share your values and beliefs as they may impact care choices.

Designate a Power of Attorney and list two or even three back-up candidates. This person will be responsible for financial, legal and personal matters, avoiding the need for guardianship.

Appointing a family member or friend as a guardian is the ideal solution. However, there are instances when the best person to be a guardian is not a family member, but a court-appointed outsider. This relieves the family of being the ones who need to inform a person suffering from dementia with the news of having to move into a nursing home facility or sifting through financial records to learn that the family home is in foreclosure. The family can focus on being supportive and loving, while the guardian deals with the sometimes harsh realities of the person’s life.

Speak with your estate planning attorney to learn about how guardianship works, and whether it may be the right move for your family.

Reference: Next Avenue (Dec. 23, 2022) “Thinking of Becoming a Guardian?”

Why Do You Need an Estate Plan?

Everyone benefits from having an estate plan. If you own property, investments, or anything of value, you need an estate plan. If you have family or dependents, you need an estate plan. Estate planning directs how assets are directed, if you become incapacitated or when you die.

The checklist for creating an estate plan includes a will, powers of attorney and assigning beneficiary account designations. Using an estate planning lawyer ensures that your plan meets all legal requirements, according to the article “What is estate planning? A strategy to safeguard your family and your finances, and ensure your plans for them get carried out as you wish” from Business Insider.

In this usage, “estate” means the things you own. An estate plan inventories everything, including your home, cars, bank accounts, life insurance policies, retirement accounts and personal possessions. It outlines in writing exactly what you want to happen with your property. It also directs who you want to handle your affairs during life and after death and who you want to inherit your assets.

Why does estate planning matter? If you die without a will, your assets may get tied up in probate, where the court oversees the distribution of your estate according to your state’s laws. Without a will and the tax planning part of estate planning, your estate may shrink and your heirs receive less.

The will is just the start of a comprehensive estate plan. It details where you want your assets to go and names an executor who will oversee your estate. If you have minor children, the will is where you name a guardian to raise your children.

A durable power of attorney designates a person to act on your behalf for legal and financial matters if you become incapacitated. Without it, family members will not be able to file tax returns, collect government benefits, manage investments and handle any financial transactions. They’ll need to go to court and have a judge appoint someone to manage these and other tasks. It’s far easier and less expensive to have this document in place than to get the courts involved.

A health care power of attorney is your opportunity to name someone to make medical decisions on your behalf if you become incapacitated. This includes choosing doctors, deciding what tests to run and whether you want to have surgery or certain treatments.

You’ll want a living will to ensure your wishes for end-of-life decisions are followed. A living will also relieves your loved one of the enormous burden of determining “what Mom would have wanted” if you become terminally ill, enter the late stages of dementia, are seriously injured, in a coma, or near the end of your life. What extreme measures do you want to be taken to prolong your life? What would you not want to be done to maintain your life?

Beneficiary designations are the forms to be completed when you open a retirement account or purchase a life insurance policy. Beneficiary designations override any instructions for these accounts set out in your will, so its very important to review and update them regularly.

Trusts are used to take assets out of your probate estate. A trust is created by an estate planning attorney and upon death, assets are distributed according to the directions of the trust. If you own a lot of assets, trusts are a useful tool to avoid estate and inheritance taxes.

Digital asset protection trusts are a way to legally transfer domain names, social media accounts and other digital assets to heirs upon your death. Emails, text messages, cloud-based storage accounts, websites and social media accounts all need to be inventoried and a plan needs to be in place to protect these assets.

Reference: Business Insider (Sep. 22, 2022) “What is estate planning? A strategy to safeguard your family and your finances, and ensure your plans for them get carried out as you wish”

What Sparks the Contesting of a Will?

A last will and testament is the document used to direct your executor to distribute assets and property according to your wishes. However, it’s not uncommon for disgruntled or distant family members or others to dispute the validity of the will. A recent article titled “5 Reasons A Law Will May Be Contested” from Vents Magazine explains the top five factors to keep in mind when preparing your will.

Undue influence is a commonly invoked reason for a challenge. If a potential beneficiary can prove the person making the will (the testator) was influenced by another person to make decisions they would not have otherwise made, a will challenge could be brought to court. Undue influence means the testator’s decision was significantly affected by a person who stood to gain something by the outcome of the will and made a concerted effort to change the testator’s mind.

Even if there was no evidence of fraud, any suspicion of the testator’s being influenced is enough for a court to accept a case. If you think someone unduly influenced a loved one, especially if they suffer from any mental frailties or dementia, you may have cause to bring a case.

Outright fraud or forgery is another reason for the will to be contested. If there have been many erasures or signature styles appear different from one document to another, there may have been fraud. An estate planning attorney should examine documents to evaluate whether there is enough cause for suspicion to challenge the will.

Improper witnesses. The testator is required to sign the will with witnesses present. In some states, only one witness is required. In most states, two witnesses must be present to sign the will in front of the testator. A beneficiary may not be a witness to the signing of the will. Some states have changed laws to allow for remote signings in response to COVID. If the rules have not been followed, the will may be invalid.

Mistaken identity seems farfetched. However, it is a common occurrence, especially when someone has a common name or more than one person in the family has the same name, and the document has not been properly signed or witnessed. This could create confusion and make the document vulnerable to a challenge. An experienced estate planning attorney will know how to prepare documents to withstand any challenges.

Capacity in the law means someone is able to understand the concept of a will and contents of the document they are signing, along with the identities of the people to whom they are leaving their assets. The person doesn’t need to have perfect mental health, so people with mild cognitive impairments, such as depression or anxiety, may make and sign a will. A medical opinion may be needed, if there might be any doubt as to whether a person had testamentary capacity when the will is signed.

A will contest can be time-consuming and expensive, so keep these issues in mind, especially if the family includes some litigious individuals.

Reference: Vents Magazine (May 6, 2022) “5 Reasons A Law Will May Be Contested”