Lawyers Reveal The Craziest (And Legal) Last Will And Testament Stories They've Dealt With

We see the "fulfilling the last will" trope in movies all the time. Someone's rich somebody dies, and they stumble into some fortune or another because of the last will. If screenwriters really want to shake things up, they add in some condition to the will, like having to spend a night in a haunted house or something. But honestly speaking, this stuff never happens in real life... right?

One Reddit user asked:

Lawyers of Reddit: What are the craziest (yet legal) last will and testament stories you had to deal with?

Look; we don't want to spoil your plans, but it looks like forcing your relatives to run a dangerous cross-country relay race to decide who gets to care for your beloved chiweenie after you're dead isn't legally enforceable. We know. We were bummed, too. Corndog deserves better than this. (If you have a Chiweenie and you didn't name it Corndog, you missed a golden opportunity, folks.)

Here are some of our favorite responses:

Chris Jericho


Military lawyer here. Had a young client come in for a will before deployment. He put a request to be buried in blue jeans, a Chris Jericho t-shirt, and his replica WWE championship belt. Happily, this airman didn't meet any misfortune on his deployment.

- Kumahito

Bus Driver

I worked at an attorney office and little older lady gave her house and her belongings to a bus driver. The bus driver was nice to her and would help her, we were all waiting for hell to break loose when her family found out.

- mommy5dearest

Smartphone Precedent

Not a lawyer, but paralegal. We had a dying client in hospital change her Will by recording it on a smart phone. It set a precedent and made the local paper. The lawyer in question has the page from the newspaper framed in his office.


The Great Stork Derby

The Great Stork Derby was when a wealthy Canadian left a substantial amount of money to whichever woman had the most children in the 10 years following his death. It was upheld through numerous court battles and 4 women tied with 9 children each. Two women were also given smaller payouts. One had 10 children (2 were stillborn), and another had more than 9 kids, but a few were illegitimate.

The guy also had some other interesting things in his will and was a known practical joker.

- splat313

The Tree

Where I went to college, there's an oak tree that was deeded to itself in a man's will. Now called The Tree That Owns Itself, it sits in the middle of a road and you have to go to one lane to drive around it. Story is that a man loved the tree so much as a kid, that around the time he died in the 1830's, he gave the tree possession of itself. This technically wouldn't stand up in a court of law, but the county and local populace has accepted it and takes care of it. The original tree actually died and the current one is a product of one of the acorns of the original!

- Schump_dawg



I work for a lawyer who does wills.

We've had a lady put in her will that one of her adult sons was not to receive his share until he visited a dentist and the other son lost 70lbs.

Another lady put in her will that she wanted her cats cremated with her when she died. Euthanized to be buried with her. I was so pissed off. I told the lawyer that's absolute bullshit. And though she agreed she had to put in as instructed and hoped that living family members at the time of her death wouldn't uphold that part. Told her that's not going to happen, human remains and animal remains do not get cremated at once. So she settled on cremated separately and joined together, then buried together.

- ALighterShadeOfPale

This Family Was All Shook Up

One of my uncles was really rich and really crazy... not in the good way. We almost never saw him, he visited us maybe once every ten years. The last time he did, he flew in just to take us to Denny's. He met my brother in an airport, was there for an hour, ate, and got on another plane and went home.

When he died he had no friends. He had driven his wife to basically drink herself to death a few years prior, so she was gone too. He left his entire estate to an Elvis impersonator. Everything.

- whatshisfaceboy

Unwanted Divorce

I was a witness to one where the lady wanted to make sure her daughter divorced her husband (when she had no intentions of doing so) if she wanted her part of the estate. Thankfully that is not legally enforceable so nothing came from it.

- MediocreAnchovies


Estate lawyer here. I once had true believers who were convinced the rapture was imminent and only saw the value of completing their estate plan when I explained the mess those of us left behind would have to deal with, including their stuff.


Embezzlement and Bigamy in the Phillipines


I mean, it's not that crazy. It's depressingly predictable. Rich old aunt the only one in her huge family with any money, having been a doctor on the Upper East Side of Manhattan. She set up a living trust to take care of her poor relations in the Philippines, to continue as a death trust whenever she died. Her favorite niece was in control of the trust, and of course the niece was responsible and even handed and never ever embezzled any of the money to set herself up as a newspaper publisher and concert producer and media mogul with new expensive cars and lots of first class pan Pacific travel, nope, not her.

Hahaha of course the trustee did all that. Hundreds of thousands of dollars missing, and an unholy mess of sifting through money transfers and property purchases in three countries. The niece also had a bigamous marriage to some loser in the Phillipines (her legal husband in north america was bedridden and dying slowly), to whom she sent buckets of her aunt's money to build a luxury villa. She vehemently denied such a relationship existed. She also had photos of the "wedding" on her Facebook page. Not the smartest embezzler out there.

From where I sat, in the attorney's office representing the poor relations trying to stop the trustee's embezzlement, the craziest part of it all was that after years of fighting, we finally got complete financial disclosure for the trust on like December 22, and it was such a Christmas miracle that I almost put off my Christmas trip to NYC to gleefully pour through every poorly redacted line of it. Also, we had the rich old aunt's ashes sitting on our bookshelf for years, since the dispute about what to do with her remains was part of it all.

- CountyKildare

One Third Of One Percent

The lawyer who did my & my husband's will told us this one.

This couple had 3 children whose jobs were doctor, lawyer, and teacher. They split their assets 33/33/34, in favor of the teacher who earned less money than the doctor and lawyer. The doctor and lawyer contested the will over .33% each.

This is why our lawyer recommended that we include a clause in our will to exclude anyone who contested our will.

- Sufganiya

Thanks, Internet! 

Lawyer here: two years ago a guy (70s, grandpa) came in to my old firm to revise his will to give something to everyone except this one granddaughter who was about 17-19. The reason? He saw her uhh.... sexy social media postings.

- butterfly105

It's Over Because Of Rover

I don't normally do wills in my practice, but when I passed the bar I had a friend who insisted that I do his will. He was trying to give me business, which is incredibly kind. He was a middle aged, single guy, so it was simple enough. When we sat down to do the paperwork, the first thing I asked him about was who he wanted to take his dog if he died before the dog.

He had never thought about it before, and he just could not handle the thought of leaving his dog. He made excuses and begged off for a long time before just abandoning writing his will. I completely understand, it's not like a fun thing to do.

- sykopoet

A Dollar And A Note

Not a lawyer, but had a fun story with my grandma's brother's will.

For the last 10 to 15 yrs he had been paying child support and sending money to this lady who he said was his girlfriend and the child "they had together".

For years his other children and my grandma had been trying to convince him that the girl was obviously not his.

The "girlfriend" would appear only on payday and stay the bare minimum. The girl called another guy dad and had his last name. The "girlfriend" insisted he was her friend, but the other children found out he lived with her and all. It was obvious to everyone, except to my great-uncle who we believe was just happy for a nice-looking lady to visit him.

He payed for their whole lives, house/school/vacations.

The day he died she was the first one at the door.

He left her and her kid $1 each, with a note saying he had given them their inheritance while alive.

- LuckyLucre

Nude Photos


Disclaimer, this was a story told to me by an estates attorney.

Deceased's (father) son was a prior client of the attorney. Son did not really talk his father but wanted to make sure estate was wrapped up properly. They did not know if a will existed but knew dad had a safety deposit box.

Get a court order to open the box and sure enough a will was in there. The will though left a lions share of his estate (maybe a few thousand dollars) to a woman who no one knew. In with the will were also pictures of a nude woman and a stage name something like "cinnamon" or "candy," written on the back. They were able to put 2 and 2 together and realized that the father had left part of his estate to a stripper who he enjoyed visiting in his older age.

She had no idea and they had to track her down which was also a nightmare I'm told. Imagine teams of lawyers going to strip clubs trying to find this specific dancer. They finally found her and she came to the office for a check accompanied by a "male friend" (lawyer assumes he was a pimp). She ended up receiving, as I mentioned above, a few thousand but it always got me how the old guy left nude photos of her to help identify her.

- souslawyer54

The Horse

Not a lawyer, a financial adviser. A woman left about a million USD to her horse. My client is a horse. We manage his investments...the sister of the deceased pulls out about 3-4% annually to care for the beneficiary of the trust.

- ZachMartin

Irrevocable Trust

Not in the will, but my mother left her estate to me, and my four brothers, share and share alike. My oldest brother was physically, and mentally disabled. A few days before she died, she asked one of my other brothers to have all of us turn our shares over to my disabled brother.

Keep in mind; he was getting disability, lived in a nice group home, had all of his medical covered, and risked losing all of this if he had any substantial assets. Also, they asked that the money be put into an irrevocable trust. This means that if my brother passed, the money would go to the State of Pennsylvania.

My brother was in very poor health, and my Mother's wishes were never codified into her written will. We met for a breakfast meeting (me, and my three other brothers), and two of us agreed to the trust, two of us did not. I did not. I have an adult disabled daughter, and was much more fluent in the ins and out of providing for a disabled child. I didn't want to come across as greedy, or mean, but I knew what the irrevocable trust meant, and they didn't. There was no bad blood, and we all respected each other's decisions.

While my brother was in the process of setting up the trust, our disabled brother died of natural causes related to this disability. Two of us had chosen to not make an emotional decision in the wake of my mother's death. In the end, her wishes never came to fruition because of my brother's death - but if we had all agreed to these wishes, the State of Pennsylvania would have made out like a bandit.

- PopeJohnsonAgain

My 2 Cents

My brother used to be a paralegal, and he said that a group of three siblings (I believe two brothers and a sister) almost came to blows because the inheritance didn't divide into three evenly; there were two pennies left over.

- Gottscheace

Zoo Trip


We had a man put in his will that his family was to go to the zoo immediately after his burial (that day). We thought that was more heart warming.

- ALighterShadeOfPale

The Revolver

My dad is a lawyer. He once wrote a will for a man who was in his late 80's and had end stage cancer. He was a big fan of weapons and wanted to give them to my dad. The old man said he wanted to give dad two shotguns, a Glock and a revolver. My dad totally wanted them, but rather than take them right away he recommended that they just be written in the will. My country's law says you can only own 5 weapons at a time, but if you inherit them, it doesn't add to the limit. My dad had already 4 at the time so he would have to give some up if the old man just gave him the guns.

So they made a testament and in the written will he gave him the weapons - except for the revolver. He said it was "because it was his favorite and didn't want to give it away yet." My dad said he instantly had a bad feeling that there was another reason the man wanted to keep it. Two weeks later the guy shot himself - with that revolver.

Dad still hasn't got the revolver because the police still have it in possession as evidence. Dad said he felt like this guy wanted the choice to end his life on his own terms instead if waiting for the cancer to win.

- SaschaCawa

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