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

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.