What the Karen Read Case Reveals About Estate Planning Gone Wrong
When it comes to estate planning, most people think in terms of wills and trusts, powers of attorney, and maybe taxes if they’ve done their homework. But every once in a while, a high-profile criminal case throws a spotlight on what can go wrong - horribly wrong - when someone dies with no estate plan in place.
That’s exactly what we’re seeing in the case of Karen Read, who is currently standing trial for the murder of her boyfriend, Boston police officer John O’Keefe. The twists and turns of the case are making headlines, but what’s happening behind the scenes—particularly in probate court—is, for us estate planners, a cautionary tale.
Let’s dig into what’s happening, what it means from a legal and financial standpoint, and most importantly, what lessons it holds for anyone who thinks they don’t need an estate plan—especially if they live in Massachusetts.
What Is the Karen Read Case About?
For those who haven’t been following closely, Karen Read is accused of killing her boyfriend, John O’Keefe, in January 2022. Prosecutors allege she struck him with her SUV and left him outside to die during a snowstorm. Read has pleaded not guilty and claims she’s being framed. See this timeline from CBS News.
The first criminal trial resulted in a deadlocked jury and the judge declared a mistrial. Now, the prosecutors are taking another crack at it, with the new trial set to begin on April 1, 2025. The evidence is all over the place, and dueling experts point at different ways John could have died.
But while the criminal case is ongoing, there’s another drama quietly unfolding in the probate court—one that’s all too familiar to us: John O’Keefe died without a will. That means, no matter what he might have said or wanted, the state of Massachusetts is now deciding who gets what, who takes care of whom, and how it all plays out.
What Happens When Someone Dies Without a Will in Massachusetts?
In Massachusetts, if you die without a will (legally known as dying intestate), the Commonwealth steps in to apply a default set of rules about who inherits your estate. These rules might seem logical on paper, but they don’t account for real-life nuance—like unmarried couples, guardianship relationships, or strained family dynamics.
Because John O’Keefe had no will, the court appointed Paul O’Keefe as conservator to manage the affairs of the children he had been guardian to. Let that sink in: this man was raising children—his late sister’s kids—but had no legal plan in place to determine what would happen to them if he passed away. So the courts stepped in. John’s brother Paul was appointed, for now, and he is taking care of the children. Is this what John wanted? There’s no way to know.
What About Karen Read? Could She Inherit?
You might be wondering: if Karen Read was his girlfriend, does she stand to inherit anything? The answer is no, and not just because they weren’t married.
Massachusetts law makes it clear: unmarried partners aren’t entitled to inherit unless you say so in a will or trust. If you don’t put it in writing, your partner gets nothing. Since John had no Will, his brother Paul was appointed as Personal Representative to his estate.
Even if John had named Karen as a beneficiary on a retirement account or life insurance policy, another law could block that, too. Enter: the Slayer Rule.
The Slayer Rule in Massachusetts
Massachusetts has what’s known as a Slayer Statute, which prevents anyone who kills or is accused of killing someone from inheriting from them. This applies to wills, trusts, retirement accounts, and insurance policies. If you kill someone you forfeit your right to inherit. If you are even under suspicion, inheritance is paused, pending the criminal proceedings.
We’ve written about this before—most notably in our post about Brian Walshe, who was accused of murdering his wife Ana and couldn’t inherit from her estate. You can read that blog here.
In Karen Read’s case, even if she had been named in a will or on a policy (which she wasn’t), the Slayer Rule would disqualify her if she’s found guilty. Did John want her to inherit from him? We don’t know, because he had no plan.
But That’s Not the End of It—Here Comes the Civil Suit
Karen Read isn’t just facing criminal charges. She’s also being sued in civil court by John O’Keefe’s family and his estate. This wrongful death suit is a completely separate case, and here’s the scary part: you don’t have to be convicted in criminal court to lose in civil court.
Remember O.J. Simpson? He was acquitted in his murder trial but found liable in civil court—and ordered to pay millions.
The same could happen here. And that brings us to another massive hole in most people’s estate plans:
What happens if someone sues your estate? What if you die and someone tries to go after what you’ve left behind? What if your children are suddenly on the hook for your legal mess?
This is where traditional estate planning simply doesn’t cut it.
Why a Basic Will or Living Trust Isn’t Enough
Most estate planning attorneys push the same tired set of documents: a will, maybe a revocable trust, powers of attorney, and a health care proxy. But here’s what they won’t tell you:
Those documents won’t protect your assets from lawsuits.
They won’t prevent someone like Karen Read—or someone suing on her behalf—from trying to access your accounts. And they don’t do much to guard against chaos when there’s no clear guardian named for your kids or heirs.
That’s why we created something different.
The 20/20 Hindsight Trust™ – Protection When You Need It Most
At Monteforte Law, we developed the 20/20 Hindsight Trust™ to solve problems just like the ones in this case. It’s a proprietary trust we offer our clients that goes far beyond what a standard estate plan can do.
Here’s how it works:
- Keeps You Out of Probate: When someone dies with a will—or no will at all—their estate goes through probate, which is public, time-consuming, and expensive. It’s also where lawsuits show up. The 20/20 Hindsight Trust keeps your assets private and protected, avoiding probate entirely.
- Built-In Lawsuit Protection: One of the most powerful features of this trust is its lawsuit shield. If someone tries to sue your estate—whether it’s a wrongful death claim, creditor claim, or anything else—the trust structure makes it extremely difficult for them to access your assets.
On the other side of the coin, Karen Read is being sued personally, which means her personal assets could be used to pay a judgment if she loses. If she had a 20/20 Hindsight Trust, her assets would be shielded from the suit.
- Excludes the Wrong People: Let’s say you have someone in your life you don’t want inheriting if things go south—like an ex-spouse, a disgruntled relative, or even a significant other with a shady past. The 20/20 Hindsight Trust lets you include “disqualification triggers” so those people are automatically excluded in specific situations, including investigations, legal claims, or criminal charges.
- Protects the Kids: If John had this trust, he could have clearly spelled out what would happen to the children he was guardian to. He could have named a successor guardian and allocated funds for their care and education. Instead, the state will decide, and the kids could be thrown into the middle of a courtroom drama.
This Isn’t Just About Karen Read or John O’Keefe. This is about you—and what could happen to your family if something unexpected happens to you.
You don’t need to be accused of a crime or caught in a media storm for your estate to end up in court. All it takes is:
• No will
• No trust
• The wrong person trying to inherit
• A family fight
• Or a lawsuit you never saw coming
And suddenly, everything you worked for is at risk.
Real Numbers. Real Damage.
Let’s say you’ve built up a modest estate: $700,000 in life insurance, a $800,000 home, and a $600,000 retirement account. That’s $2.1 million in total assets.
If your plan is outdated—or nonexistent—here’s what you could lose:
• $60,000–$100,000 in probate and legal fees
• $100,000–$400,000 in estate taxes
• Up to 40% of your IRA in forced income taxes under the SECURE Act
• Even more if someone sues your estate or challenges your plan in court
All of it could be prevented with the right structure. And the 20/20 Hindsight Trust™ is designed to do exactly that.
Don’t Wait Until It’s Too Late
John O’Keefe, by most accounts, was a good man. A Boston police officer. A guardian to his sister’s children. A respected member of his community. His legacy is certainly tarnished by the testimony about he and his friends regularly driving drunk, yet he is still remembered by most as a decent man.
But he died without a will. And because of that, everything he left behind—his assets, his kids, and his wishes—are left to the mercy of the courts. Don’t let the same thing happen to your family.
Want to Learn More? Join Our Seminar
We don’t do cookie-cutter plans. We don’t sell fear. We educate. And we give you tools that actually work—even when things go sideways.
Join one of our upcoming estate planning seminars to learn:
• How the 20/20 Hindsight Trust™ and the Retirement Protection Trust™ work
• Why most estate plans fail in the real world
• What SECURE 2.0 means for your retirement accounts
• How to protect your estate from lawsuits, taxes, and chaos
Spots are limited, and these seminars fill up fast.
Because once you’re gone, your plan is locked in—and there’s no second chance to fix it. John O’Keefe wasn’t expecting to die that night. And Karen Read wasn’t expecting to be on trial for her life. Our lives can change in an instant.
