In everyone's will, they get the last word and say-so when it comes to everything they own. Some requests are fairly easy, but some are straight up petty. Sometimes, these wills are a dying person's last chance to get back at the greedy family that took them for granted and other times, it's the last attempt for control freaks to make their final demands and manipulate their put-upon relatives. These lawyers share the strangest requests and rules they saw in their clients' wills. Content has been edited for clarity.
Charity Comes With A Price
“I had a guy be charitable when we were drafting his will – $1 million to his church, $2 million to a local hospital, and another $2 million to the American Heart Association.
When we gave him a quote on how much it cost to draft the will (it wasn’t much because it was a rather straightforward document), he asked for a payment plan. He couldn’t afford the will.
The dude had no money.
He thought you could just leave money to people/organizations and the government would foot the bill. He was also the sort that became visibly angry talking about welfare and government ‘hand-outs,’ which made his thinking even funnier to me.”
The Caretaker Struck Gold… Her Family, Not So Much
“A good friend of mine looked after this elderly woman. She was his neighbor and, as far as he knew, she had no family. So, every day he was at her place when he wasn’t working. I met her a few times. Sweet old lady. She had three cats that were her babies, spoiled them to no end. She had a ‘cat room’ for them with three separate beds and three separate litter boxes, bowls, etc.
Well, one day after looking after her for a few years, he walked in to find she passed in her sleep. Later, he found out she named him in her will. He got to the reading to find three 20-something ladies there, too. He found out they were the lady’s daughters. It turned out that the lady had moved across the country unannounced a few years earlier, and disappeared from the daughters’ lives.
The old woman left my buddy $19 million. She left the cats to a lifelong friend from her home state, donated all her belongings to Salvation Army, and left her daughters each ‘a single litter box and all of its contents’ along with each a single $20 bill to ‘give them each a last taste of all she was to them.’
The sweet old lady is my hero.”
Great-Uncle’s Final Revenge
“‘To my daughter Anne, who created my beautiful granddaughter Jane, and her dear fourth husband John, who laid hands on my Jane, I leave $1, you money-grubbing jerks. To Jane, I leave all of my monetary assets, save $5,000, and my best weapon, which I leave to my son Bill, on the condition that he beats John bloody during the time between my funeral and my burial. Jane, bail your uncle out of jail, please.’
Other than names, this is the exact wording of a great uncle’s will, part of it anyway. At age 9, Jane told her mother that John had violated her and her mother told her she deserved it for being a flirty girl. So, Great-Uncle took Jane in and raised her, and his two kids got exactly what it says. His son also got a truck and, technically, a house, although he only kept it until Jane was a legal adult and could afford the tax on it. Bill got full custody of Jane when his father died and he put every penny of her money into a trust fund to mature when she was 25 because he felt like his sister would try to get the money and he was right.
Bill got his $5,000. He didn’t get arrested though because John had a warrant on him, so they didn’t dare call the cops. Bill did kindly informed the police of his whereabouts a few weeks later.”
“They Can Have The Stupid Money, But I’m Gonna Make Them Suffer For It.’
“Apparently, there was this rich old broad (‘ROB’ from here on out), and her family had been waiting for her to die for years so they could get her money. They were real stuck up, crappy people, and ROB hated them. But, I guess she either didn’t have anyone else to leave her money to, or she figured that her awful family would contest the will if everything wasn’t left to them. Knowing how status-conscious these crappy relatives are, ROB decided, ‘Fine, they can have the stupid money, but I’m gonna make them suffer for it.’
So, when ROB finally passed away, her lawyer approached the family with her instructions for how her funeral was to be run. According to ROB’s will, the only way they could get the money is if they followed these instructions to the letter. I don’t remember all the absurd details in her instructions, except for the pièce de résistance:
ROB required an open-casket funeral, with all family members in attendance, and demanded that her corpse be dressed up like Bozo The Clown – makeup, red nose, crazy hair, massive shoes, the works.
The family tried to protest, but ROB’s lawyer had tied this thing up beautifully, perfectly ironclad. They either attended the Bozo the Clown funeral, or they didn’t get a dime. So, they did it. These stuck-up jerks had to stand there for hours, glowering, taking weird looks from all their friends and neighbors as people got close to the casket and realized ROB was dressed like a freaking clown.
According to a funeral parlor employee (who had dressed ROB and applied the makeup), the best part of the service came when they tried to shut the casket and couldn’t because the massive shoes got in the way. They had to bend these 24-inch shoes in half to get the lid closed.
I never had the honor of meeting the brilliant, cantankerous old witch, but she’s one of my biggest heroes.”
“You Will Never Forget That I Loved You Less”
“A client had two sons. He left a whole bunch of specific distributions to one of the sons: his truck, weapon collection, etc. To the other son he specifically left one thing: a poster of himself in high school.
I have no idea if there was some significance or sentimental value behind the poster or if it was more of a ‘look at what I’m giving your brother, and here’s a poster of me so you will never forget that I loved you less.'”
“Definitely The Biggest ‘Holy Crap’ Moment Of My Career”
“Readings aren’t typical with wills, those are mostly a Hollywood thing. Still, sometimes the will specifies a reading, usually (at least I’ve found) when the deceased wants to stab someone in the back in front of the rest of the family.
The strangest, and most embarrassing, reading was in a room crowded with relatives when a man who died fairly young (massive heart attack, in his early 50s) left everything to his 26-year-old step-daughter, which was quite a lot of money and property. Two ex-wives and children from the first marriage got nothing, nor did siblings, nieces, nephews, etc. The will specified that a DVD had to be played to explain why the step-daughter was getting everything. Like everyone else, I thought it would be the guy explaining the big ‘Get stuffed’ to the rest of the family.
What followed was completely unexpected. It was a hidden camera recording of the guy and his step-daughter (at about age 15) wildly fooling around, which they both were clearly enjoying. The video started in mid-coitus, with her screaming ‘Yes. Oh god, yes!’ It had obviously been edited to start with maximum shock value, and it worked, because it took about 30 seconds for me to recover enough to turn the thing off. Definitely the biggest ‘holy crap’ moment of my career.
I later learned that the guy and his step-daughter had been fooling around since she was 14, all the way to when he died (when she was 26). Apparently, this is second-hand and I can’t confirm. There were multiple clips of various video bits through the ages on the DVD. At the end of the DVD, the guy explained that the step-daughter got everything because she had been ‘the best lay of his life.’
The worst part: the will specified that I was to give every single family member their own copy of the DVD. The copies had been kept in a box and had been distributed prior to the showing, so everyone had ‘The Best Moments Of’ in their hands, at the time the DVD was playing.
Epilogue: the family sued and lost, believe it or not. The girl got to keep everything.”
He Made Sure His Kids All Got A “Fair” Cut
“My mom only works for crazy rich people. The worst will she ever told me about was this old guy who was close to 90. He wanted it so that when he died, all of his millions would go into a trust for his kids and his kids would never be able to touch it, but they could collect the interest it generated.
So, he had my mom set him up with this group of accountants who would manage the trust, and he specifically arranged a plan with them to manage the account in such a way that their yearly billing would almost exactly match the interest to be made. So, when he died, his kids would inherit millions, but will only be able to spend $35 a year that the kids would have to split between them.”
Really Letting Them Have It From Beyond The Grave
“My significant other’s father was a lawyer, and he always said his favorite story was of this old money lady he knew of. She was worth around $15 million and had five kids, one of whom married a horrible man who would spout just the foulest crap against anyone who wasn’t a white, rich, able-bodied, Christian male. When she died, each child got $3 million, except for the crap baby’s wife. She donated that money to things like HBCU’s, Planned Parenthood, the Special Olympics, her local synagogue and food banks because: ‘You both deserve to die penniless and hating each other for being awful human beings.'”
Guess You CAN Take It With You!
“I did a few pro bono wills up on the reservation. This big guy asks me to give everything back to the tribe because he has no living immediate family. No problem. Then he has one exception: his Vietnam era motorcycle. Said it was the first thing he bought after getting home. Wants to be buried with it.
I should clarify – not with it, literally on it and in riding position. I helped him set aside the funds necessary to do it and have a lot prepaid for. The dude was awesome!'”
Mom Had Some Strong Views About Her Son-In-Law
“My favorite story has to be a woman who had a massive falling out with her daughter because she hated the husband that the daughter had chosen. This feud went on for years to the point where they never had any contact, and whenever they did, things would just get pretty ugly, with the daughter refusing to leave the husband and the mother demanding that she did.
So when the time came to read the will, it turned out that the mother had left a good portion of money to the daughter (10/20% of the sizable estate – there were three or four children), on the sole condition that the daughter change her surname and her children’s surname back to her maiden name, effectively removing this hated husband’s name and significance on their family tree.
By the sounds of it, this was a real sticking point for the daughter and (I was at the law firm whilst this whole saga was going on) the solicitors were confident that the daughter was going to forsake her inheritance (which was a pretty large one) in order to keep her husband’s name.”
“They Wanted To Leave Everything To The Baby Boy”
“I only worked in probate for a little while, but I think the thing that struck me most was a married couple coming in with a small baby to make a will together.
They wanted to leave everything to the baby boy. Easily done, but he had been married before and had two daughters, 12 and 14, who lived with their mum. Not only did he not leave them anything in his will, he also asked for a specific clause to be put into the will saying, ‘I acknowledge my two daughters and confirm that I have deliberately omitted to provide a legacy for them,’ or words to that effect. You can’t just leave your kids out altogether if you think there’s a chance they could contest the will – the ‘prudent and loving parent’ argument: you have to make sure that everyone knows it’s a deliberate omission.
I know teenage girls can be nightmares and maybe the ex-wife was a total witch poisoning their minds, but wow. I just can’t imagine cutting your own kids out completely in favor of your new family, especially when they are so young. Harsh.”
No One Liked Him, But They All Sucked Up Anyway
“My grandfather was alone after my grandmother died some years ago. Everyone in the family was convinced that he was loaded, despite him never using a dime on anything or anyone. He gave me three spoons from the dollar store when I turned 18. But, we all knew that he owned some expensive silverware, figurines, paintings, etc.
My family is made up of greedy, self-absorbed jerks, and the old man was a greedy, self-absorbed jerk, and a disgusting old pig to boot. Nobody liked him, including me, but I liked the rest of the family even less. Everybody except me kissed his butt all the time, waiting for him to die.
At Christmas dinner when I was about 15 (and as most teens, I loved to tick my family off, in every possible way), I asked him why he didn’t sell all his stuff, move to a warmer country, and find a nice lady friend he could spend his last days with (not because I gave a crap about his wellbeing, but because any place warm, is at least 500 km from my home country and, thereby, me). He proceeded to tell me, ‘My junk doesn’t work that well anymore.’
So, hot chicks were no longer a focus in his life, but he did enjoy it immensely when the nurse came every night. The rest of the family got pretty mad at me, not because I (unintentionally) got the old pervert to talk about his junk at Christmas dinner, but because I had suggested that he use his own money to have some fun.
About 10 years later, the old pervert finally died. The only place he moved was when the family finally got him into a nursing home so that they didn’t have to take care of him. No warm place and no lady friends for gramps. They thought the money and all the expensive stuff was safe.
Some years prior, I had told the family that It would make me more than happy if they took a long walk on a very short jetty, so I don’t know exactly what went down. But it was something like this: a short time after that memorable Christmas dinner, the old guy began to sell all his stuff to his drinking buddies, friends from the billiard club, and some other friends of his. The way he made the deal was that they could only get the stuff when he died but, in exchange, they got it dirt cheap.
There was exactly nothing left for the family, except a crapload of old bills, smut magazines, and a couple of the 1,000 sticky VHS tapes with ‘Naughty Nurse Nina,’ ‘The Nazi She-Witch Ilse,’ and so on, plus all the other stuff he had hoarded the past 80 years. I still giggle when I think about it and I hope that I had some part in his doing this because of my suggestion at that Christmas dinner.”
“The Family Was Too Much Of A Train Wreck To Handle The Will On Their Own”
“For my job, I go through wills and accompanying court documents to at a register’s office. Sometimes when I see a whole slew of documents listed in the system for a particular case, I take a few minutes to read through the crap shows:
A woman died, leaving behind six (adult) children. She had dementia or Alzheimer’s in the last two years of life, but had made a will in 2003 when she was still of sound mind. However, the one that was used was a will made in 2011 and one of the kids filed a motion to have it thrown out. It was a will made on LegalZoom that half the kids got together and had her sign, leaving the other half of the kids out of the inheritance. She was clearly in no mental state to sign it because she was already in a nursing home for her mental issues at the date signed and there was a lot off in the new will. She was referring to some of her sons as her brothers, for example. I only saw the beginnings of the court documents for that one.
This was another will I ran across recently, and I even wrote down the names so I could go back to it later and continue reading. A family of five (adult) kids and one mother. The father died when he was 25. They’re from Israel. Three of the kids live in Israel and two live in the States. The three are all on speaking terms. The other two don’t talk to anyone in the family (other than the mother). The mother died in 2009, so there was a trail of documents I got to read through and it was insane.
Basically, Pinhas, one of her sons in the states, was named as the executor of her will when she made one back in 2005 when she was diagnosed with some kind of heart condition. She came over to the States around then from Israel so Pinhas could care for her. The other son in the States, Shlomo, was a piece of crap who basically leeched off his dying mother and lived with Pinhas for free. The other three in Israel had nothing to do with her after she became ill. So, she died in 2009, leaving behind $150,000 worth of property in Israel and a few thousand dollars in personal items (not too much because her illness and Shlomo sucked her accounts dry).
After her death, Pinhas wanted to use the remainder of her money (not including her property worth) to ensure she would be buried in Israel next to her husband, grandfather, and son – something she obviously would have wanted. However, the three kids in Israel went behind Pinhas’ back somehow and buried her in Maryland to save the funeral money so they could pocket it. Pinhas flipped his lid because he was loyal to his mother. Not only that, but his siblings put her property up for sale in Israel without Pinhas’ consent (and he has the final say since he’s in charge of her affairs). The reason the kids got away with burying her in Maryland was that the lawyer who drew up her will in 2005 messed up and didn’t put in a clause about her burial wishes, and Pinhas, whose first language is not English, did not notice until after her death.
So Pinhas took his siblings to court, trying to get money back to bury the mother in Israel, and the siblings countersued saying that he was blocking the sale of her property in Israel (which he was – he wanted to honor her burial wishes first).
I read a court transcription where the judge appointed a judicial official as the new will executor because he said the family was too much of a train wreck to handle it on their own.
It’s a really sad story. Pinhas’ dialogue in the court transcription is so defeated. He says something along the lines of, ‘Will this new man (the new executor) do his best to honor my mother?’ I feel bad for getting entertainment out of reading it at work. I guess it’s the same thing as staring at a bad car accident.”
He Made His Family Work For Their Inheritance
“I am an executor of one of my millionaire friend’s will. He left the house and whatever money that was in the bank to his wife. The vast majority of his fortune was in cash, however, and had been hidden all around his sizable estate. He had been secretly hiding it for years. He didn’t get on with his family well and decided to make them work for it themselves since they never helped him with his business. Whoever finds a package gets to keep it. There are packages all over the place. Some parts of the house, extensions, outhouses, etc. will have to demolish to find them. His final middle finger to a spoiled family who just expected him to provide them with everything they ever wanted.”
Going To The Dogs
“Man, have I seen some bad ones recently. I had this little old lady come in who wanted a referral from one of our clients who was an accountant. He said she was a little bit strange but nothing too odd. She had four children, her husband had passed, and she had a couple hundred thousand dollars in various bank accounts, plus a house.
So, she appointed her friend as executor and trustee, with the direction to sell her house when she dies. A sizable portion of her estate was to go to some weird church. The balance of her estate was to be invested and used to house her three little dogs or any dogs that she has at her death with the direction that her trustee looked after the dogs.
Those dogs are going to be wealthier than me in a couple of years.”
They Left Money For Their Daughters’ Weddings, But With A Catch
“I used to be a paralegal. I wrote up a trust for a couple who left an allocated amount of money to cover the wedding of each of their three daughters, with some very specific guidelines.
The girl had to get married in the church the parents got married in. She had to be marrying a ‘white Christian, who has been male since birth.’ Prior to the marriage, they had to complete a reading list of 10 books on finance and relationships. They also both had to be college graduates, without loans.
I felt like a jerk typing that crap up. There was a bunch of other weird crap in that trust, but that’s the part I remember most clearly.”
“Since He Is So Worried About Whether My Funeral Is Paid For…”
“Most of our wills we read we had written in the first place, so it was rare that there were any surprises. Also, for the most part, people already read the wills before they came to our office for the next steps. But there was the one:
A man died with three sons. To the oldest, he had a paragraph written recounting a story in which he had asked the oldest son what he wanted of some collection of tools in the shop, and the son had replied, ‘Nothing, it’s all junk.’ The paragraph concluded with, ‘I shall honor his wishes and give him NOTHING.’
To the middle son, he had a paragraph recounting a conversation in which the middle son had asked if the dad had made plans for his burial and funeral, etc. to make sure they were paid up ahead of time unlike some other relatives had done. The paragraph concluded with, ‘Since he is so worried about whether my funeral is paid for, I shall honor his wishes, and so my burial and funeral arrangements shall be paid out of HIS share of my estate.’ The youngest son had managed to not tick Dad off recently and would have gotten most of the estate.
By the time we had finished reviewing the will, the three agreed to just ignore it and divide everything equally among them (after paying all the bills, of course).”