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178: 3 Critical Estate Planning Lessons from Richard Simmons’ Legacy Battles

April 25, 2025

In this episode of Absolute Trust Talk, host Kirsten Howe examines the estate complications following Richard Simmons’ death in July 2023. She details the ongoing legal dispute between Simmons’ brother Leonard (named trustee) and Teresa, his housekeeper of 30 years who briefly served as co-trustee before a contested resignation. The conflict centers around approximately $1 million in personal property—primarily jewelry—that Teresa allegedly took when evicted from Simmons’ home. While Teresa claims Simmons gifted her the jewelry in 2014, Leonard argues documentation proves otherwise. Kirsten extracts three valuable lessons: first, avoid naming co-trustees, especially in complex estates where a professional trustee would be more effective; second, document valuable lifetime gifts to prevent future disputes; and third, include specific provisions for non-owner residents in your estate plan to prevent eviction complications. This case study highlights how proper estate planning can prevent family conflicts, protect valuable assets, and ensure thoughtful treatment of longtime household members after death.

Time-stamped Show Notes:

0:00 Introduction

1:30 Meet the central figures in this estate drama: Teresa, the housekeeper, vs. Leonard, the brother.

2:05 From co-trustee to eviction, let’s talk more about the shocking timeline after Simmons’ death.

3:15 The million-dollar mystery: where did Richard Simmons’ valuable jewelry disappear to?

4:20 Next, we’ll discuss the number one estate planning lesson this case reveals: why co-trustees can transform estates into battlegrounds.

5:45 Estate Planning Lesson #2: Gifting jewelry? Why documentation might be your best accessory

6:30 And last but not least, estate planning lesson number three, the critical provision that could have prevented a housekeeper’s eviction.

Transcript:

Hello and welcome to Absolute Trust Talk. I’m Kirsten Howe. I am the host of Absolute Trust Talk, which is our podcast here at Absolute Trust Council. Usually, I have a guest, or I have one of my associate attorneys here with me, and for various technical and other reasons, we aren’t able to make that happen today, but we’re going to go ahead anyway, and you get just me whether that’s a good thing or a bad thing. That’s up to you. I don’t know.

I have a celebrity estate plan that I want to talk about today because there are a few very important lessons I think we can learn from this one. And I’m talking about Richard Simmons, who, if you’re my age, you remember, was very famous back in the day as an exercise and health and fitness personality. He had TV shows where he did what we used to call aerobics on TV with people. And he was very inspirational. He got a lot of people up and moving and caring about their health, and that was a kind of a new thing way back when.

Anyway, Richard Simmons passed away in July of last year, and he had been a single person living in his home. He had a long-time caregiver, or I guess the housekeeper really is what she was. A long-time housekeeper, something like 30 years. She had lived with him and helped him out. She was an employee. Her name is Teresa. Richard also had a brother. His name is Leonard, and Leonard was named his trustee, executor, and administrator of his estate. Apparently, he named Teresa and Leonard as co-trustees of his trust.

After Richard died, pretty quickly after that, Teresa resigned as co-trustee, and then she came back and filed a petition in court saying, “I don’t—I didn’t want to resign. I was coerced into resigning.” So, there’s that issue pending out there. Teresa, as I said, had been living in Richard’s home with him for many, many years, and after he died in July, apparently, she had to be evicted in September. I’m unsure about the details of that, but I’m sure that was not a pleasant experience for her.

What has happened is that the trustee, who is currently just Leonard, has filed an action against Teresa, claiming that she took a bunch of tangible personal property out of the home that she wasn’t entitled to. And remember, she had been living there after he died for a couple of months. Apparently, what Leonard is claiming is missing is worth about a million dollars, and a lot of it was jewelry. And there were some other items, you know, like some of his workout wear, other things like that, maybe a little bit of artwork, but I think the primary thing was his jewelry.

Teresa claims that she was given the jewelry ten years before Richard passed away in 2014. Allegations are being exchanged. Leonard argued in a court document that there was a document signed by Richard indicating that he actually still owned the jewelry at the time of his death, or at least when he signed that document. Thus, there is a factual dispute as to whether the jewelry was given to Teresa many years ago or whether she improperly took it when she left the house. There is a considerable mess going on that we can learn a little from.

What I would say the number one lesson that I pull out of this one is, and we’ve said this numerous times before on Absolute Trust Talk, it’s usually not a good idea to name co-trustees because, you know, any kind of, any large estate in particular, there is a possibility that there’s going to be trouble. Even in a small estate, there’s a possibility there’s going to be trouble. When you have co-trustees, you just really amplify that possibility. It’s very difficult to get the work done, get it done efficiently. And if you have co-trustees who don’t agree with each other or don’t get along, it’s going to be a mess.

Number one, please consider not naming co-trustees. And here, in this case, sort of one part A, I would say this was likely a large estate. I don’t know how much value there was there, but I would have recommended a client like that to name a professional—name a Trust Company, name somebody who’s just going to be impartial, get the job done. And it’s a complex estate. There are allegations in there about a documentary that Teresa was working on, possibly Leonard was working on. There’s some intellectual property, some name, image, likeness issues, just things that are more complicated than most of the rest of us have in our estates, and that seems like something better suited for a professional to sort out. So that’s the main thing. Don’t name co-trustees.

Number two, I would say—and I hadn’t thought about this much before—but if you are making gifts of very valuable, tangible property during your lifetime, it’s not a bad idea to document that so that later on, there’s not a dispute because those items, they don’t have any ownership papers. There’s not a, you know, there’s not a pink slip for a diamond necklace. You’ve got to somehow document that. No, that’s not mine anymore. I, in fact, did give that away. I think that’s a good idea. No, most people don’t do that. But again, this—people who are wealthy have valuable jewelry, and they can do that.

And number three, this one does apply to many of my clients. If you have someone living with you in your home and they don’t own the home, you have to discuss that in your estate plan. So, in this case, I don’t know whether he did or not, but if Teresa had to be evicted, it sounds like there wasn’t any provision for her, but there could have been a provision that said Teresa gets—my trustee has to give Teresa at least six months to move out of my house after my death, something like that, something thoughtful and human. Those kinds of issues have to be covered; otherwise, the trustee’s job is to get anybody who doesn’t belong there out, and so a lot of hassle could have been avoided by that.

So those are our lessons from the Richard Simmons estate. I hope some of it was helpful to you, and that anyway you enjoyed hearing it, so thanks for joining me today, and I look forward to connecting with you next time.

Resources Related to This Episode:

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Categories: Celebrity Estates, Estate Planning, Inheritance Disputes, Podcasts, Probate Litigation, Will and Trust Administration Tags: , , , , , , , , , ,

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