From Reddit. I hope I got it all, it should be memorialized forever.

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Congratulations! You just won millions of dollars in the lottery! That’s great.

Now you’re fucked.

No really.

You are.

You’re fucked. If you just want to skip the biographical tales of woe of some of the math-tax protagonists, skip on down to the next comment. To see what to do in the event you win the lottery.

You see, it’s something of an open secret that winners of obnoxiously large jackpots tend to end up badly with alarming regularity. Not the $1 million dollar winners. But anyone in the nine-figure range is at high risk. Eight-figures? Pretty likely to be screwed. Seven-figures? Yep. Painful. Perhaps this is a consequence of the sample. The demographics of lottery players might be exactly the wrong people to win large sums of money. Or perhaps money is the root of all evil. Either way, you are going to have to be careful. Don’t believe me? Consider this:

Large jackpot winners face double digit multiples of probability versus the general population to be the victim of:

Homicide (something like 20x more likely)

Drug overdose

Bankruptcy (how's that for irony?)

Kidnapping

And triple digit multiples of probability versus the general population rate to be:

Convicted of drunk driving

The victim of Homicide (at the hands of a family member) 120x more likely in this case, ain't love grand?

A defendant in a civil lawsuit

A defendant in felony criminal proceedings

Believe it or not, your biggest enemy if you suddenly become possessed of large sums of money is… you. At least you will have the consolation of meeting your fate by your own hand. But if you can’t manage it on your own, don’t worry. There are any number of willing participants ready to help you start your vicious downward spiral for you. Mind you, many of these will be “friends,” “friendly neighbors,” or “family.” Often, they won’t even have evil intentions. But, as I’m sure you know, that makes little difference in the end. Most aren’t evil. Most aren’t malicious. Some are. None are good for you.

Jack Whittaker, a Johnny Cash attired, West Virginia native, is the poster boy for the dangers of a lump sum award. In 2002 Mr. Whittaker (55 years old at the time) won what was, also at the time, the largest single award jackpot in U.S. history. $315 million. At the time, he planned to live as if nothing had changed, or so he said. He was remarkably modest and decent before the jackpot, and his ship sure came in, right? Wrong.

Mr. Whittaker became the subject of a number of personal challenges, escalating into personal tragedies, complicated by a number of legal troubles.

Whittaker wasn’t a typical lottery winner either. His net worth at the time of his winnings was in excess of $15 million, owing to his ownership of a successful contracting firm in West Virginia. His claim to want to live “as if nothing had changed” actually seemed plausible. He should have been well equipped for wealth. He was already quite wealthy, after all. By all accounts he was somewhat modest, low profile, generous and good natured. He should have coasted off into the sunset. Yeah. Not exactly.

Whittaker took the all-cash option, $170 million, instead of the annuity option, and took possession of $114 million in cash after $56 million in taxes. After that, things went south.

Whittaker quickly became the subject of a number of financial stalkers, who would lurk at his regular breakfast hideout and accost him with suggestions for how to spend his money. They were unemployed. No, an interview tomorrow morning wasn’t good enough. They needed cash NOW. Perhaps they had a sure-fire business plan. Their daughter had cancer. A niece needed dialysis. Needless to say, Whittaker stopped going to his breakfast haunt. Eventually, they began ringing his doorbell. Sometimes in the early morning. Before long he was paying off-duty deputies to protect his family. He was accused of being heartless. Cold. Stingy.

Letters poured in. Children with cancer. Diabetes. MS. You name it. He hired three people to sort the mail. A detective to filter out the false claims and the con men (and women) was retained.

Brenda, the clerk who had sold Whittaker the ticket, was a victim of collateral damage. Whittaker had written her a check for $44,000 and bought her house, but she was by no means a millionaire. Rumors that the state routinely paid the clerk who had sold the ticket 10% of the jackpot winnings hounded her. She was followed home from work. Threatened. Assaulted.

Whittaker’s car was twice broken into, by trusted acquaintances who watched him leave large amounts of cash in it. $500,000 and $200,000 were stolen in two separate instances. The thieves spiked Whittaker’s drink with prescription drugs in the first instance. The second incident was the handiwork of his granddaughter’s friends, who had been probing the girl for details on Whittaker’s cash for weeks.

Even Whittaker’s good-faith generosity was questioned. When he offered $10,000 to improve the city’s water park so that it was more handicap accessible, locals complained that he spent more money at the strip club. (Amusingly this was true).

Whittaker invested quite a bit in his own businesses, tripled the number of people his businesses employed (making him one of the larger employers in the area) and eventually had given away $14 million to charity through a foundation he set up for the purpose. This is, of course, what you are “supposed” to do. Set up a foundation. Be careful about your charity giving. It made no difference in the end.

To top it all off, Whittaker had been accused of ruining a number of marriages. His money made other men look inferior, they said, wherever he went in the small West Virginia town he called home. Resentment grew quickly. And festered. Whittaker paid four settlements related to this sort of claim. Yes, you read that right. Four.

His family and their immediate circle were quickly the victims of odds-defying numbers of overdoses, emergency room visits and even fatalities. His granddaughter, the eighteen year old “Brandi” (who Whittaker had been giving a $2100.00 per week allowance) was found dead after having been missing for several weeks. Her death was, apparently, from a drug overdose, but Whittaker suspected foul play. Her body had been wrapped in a tarp and hidden behind a rusted-out van. Her seventeen year old boyfriend had expired three months earlier in Whittaker’s vacation house, also from an overdose. Some of his friends had robbed the house after his overdose, stepping over his body to make their escape and then returning for more before stepping over his body again to leave. His parents sued for wrongful death claiming that Whittaker’s loose purse strings contributed to their son’s death. Amazingly, juries are prone to award damages in cases such as these. Whittaker settled. Again.

Even before the deaths, the local and state police had taken a special interest in Whittaker after his new-found fame. He was arrested for minor and less minor offenses many times after his winnings, despite having had a nearly spotless record before the award. Whittaker’s high profile couldn’t have helped him much in this regard.

In 18 months Whittaker had been cited for over 250 violations ranging from broken tail lights on every one of his five new cars, to improper display of renewal stickers. A lawsuit charging various police organizations with harassment went nowhere and Whittaker was hit with court costs instead.

Whittaker’s wife filed for divorce, and in the process froze a number of his assets and the accounts of his operating companies. Caesars in Atlantic City sued him for $1.5 million to cover bounced checks, caused by the asset freeze.

Today Whittaker is badly in debt, and bankruptcy looms large in his future.

But, hey, that’s just one example, right?

Wrong.

Nearly one third of multi-million dollar jackpot winners eventually declare bankruptcy. Some end up worse. To give you just a taste of the possibilities, consider the fates of:

Billie Bob Harrell, Jr.: $31 million. Texas, 1997. As of 1999: Committed suicide in the wake of incessant requests for money from friends and family. “Winning the lottery is the worst thing that ever happened to me.

William âBud❠Post: $16.2 million. Pennsylvania. 1988. In 1989: Brother hires a contract murderer to kill him and his sixth wife. Landlady sued for portion of the jackpot. Convicted of assault for firing a gun at a debt collector. Declared bankruptcy. Dead in 2006.

Evelyn Adams: $5.4 million (won TWICE 1985, 1986). As of 2001: Poor and living in a trailer gave away and gambled most of her fortune.

Suzanne Mullins: $4.2 million. Virginia. 1993. As of 2004: No assets left.

Shefik Tallmadge: $6.7 million. Arizona. 1988. As of 2005: Declared bankruptcy.

Thomas Strong: $3 million. Texas. 1993. As of 2006: Died in a shoot-out with police.

Victoria Zell: $11 million. 2001. Minnesota. As of 2006: Broke. Serving seven year sentence for vehicular manslaughter.

Karen Cohen: $1 million. Illinois. 1984. As of 2000: Filed for bankruptcy. As of 2006: Sentenced to 22 months for lying to federal bankruptcy court.

Jeffrey Dampier: $20 million. Illinois. 1996. As of 2006: Kidnapped and murdered by own sister-in-law.


Willie Hurt: $3.1 million. Michigan. 1989. As of 1991: Addicted to cocaine. Divorced. Broke. Indicted for murder.

Michael Klingebiel: $2 million. As of 1998 sued by own mother claiming he failed to share the jackpot with her.

Janite Lee: $18 million. 1993. Missouri. As of 2001: Filed for bankruptcy with $700 in assets.

EDIT: Continued below due to character limit

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[–]BlakeClass 2878 points 10 years ago

Ok, first of all, rich people don’t pay taxes. If you paid taxes, you ain’t rich. You’re at best a parvenu upper middle class.

Secondly, the current best way to give them money freely is to become a major investor of a company, make your friend the CEO, pay them in stock options, push the company to focus on making profit at all costs to raise stock prices and then have both you and your friend pull out right before it all comes crumbling down.

Or so it seems to go in the US at least.

Set up a trust for friends and a trust for family for things like education, house, car, emergency expenses

Don’t try to cheat the government. make sure you can say either you reported the large gift for tax purposes or the total is under 18k., if you must cheat you can take them on vecation and they use your gear for free but the plane ticket, meals and anything that could look like a gift is under the limit.

tax fraud is something the irs takes serously and you never know when they look. Plus you are not sympathetic to a jury so prison is likely for you.

if you give anyone more than 10k in a year (well under the limit) have your accountant deliver it all so there is plenty of evidence that you are not cheating. If you want to give over 18k have your accountant figure out how to do withholding so you friends don’t have a tax surprise.

I would think option 2 HAS TO be legal, except, you gotta modify it slightly. You don’t claim they work one hour per month. You pay them a yearly salary. And their job is to “entertain you”. Essentially you’re just paying your friends to hang out, for an unspecified amount of time every year. Which in practical terms is just you giving your friends a paycheck for the sake of giving your friends a paycheck, and sometimes you hang out. I swear to god, this HAS TO BE the basis of Adam Sandlers whole career. He makes movies where he just happens to always hang out with his friends, and somehow other people enjoy the movies too. But mostly it’s him hanging out with his friends.

Option 4 could work too. But here’s what you do. You hire a landlord. You tell that landlord "Anything they want done, you’re in charge of getting it done. ASAP. I don’t want to hear one peep out of them not getting whatever fixed. That way, they think of the landlord as the landlord, and you as just that friend they have who happens to own the houses they live in rent free. But they don’t think of you as having power over them. That’s what the landlord manager is for.

You could also buy an old hotel, fix it up, and have it serve as a homeless person shelter. I mean, this doesn’t have anything to do with your question, but if we’re just throwing money around, why not?

2. Create a company and hire them to “work” one hour a month for a big salary. If you put $25m in an account, the interest covers the salary. They get a steady bonus income with the added bonus of getting the best insurance available. Is that legal?

i think this describes at least a few production companies/celebrities like happy madison. those guys are just having fun and gettin paid

Coincidentally, for no real reason I ponder this sort of stuff too! But I’m much more pessimistic about the outcomes haha.

The real answer to this stuff would be to find a financial advisor, I suspect setting up a trust and giving out x amount of money per year is the most sane approach.

re: your options

Give them a lump sum of $X million. They eat the taxes the first year and handle the savings themselves.

Keep in mind people tend to be terrible with money/finance. And also keep in mind you cannot force people to do what you think they should do with their money.

There will be a good percentage of people that will neglect any advice about keeping that $$ for taxes & such and will come back to you in a year asking for more $$ to cover the the taxes and expenses that they are facing - after all you were the one that put them in that position.

The other percentage of people will have remembered to keep some $$ to cover taxes but will likely still bankrupt themselves in the next few years - they too will come back to you asking for more $$ because, well none of that would have happened without you starting it all.

Hopefully you’ll have a few people that didn’t blow it all & maybe invested it, or at least paid off their bills and mortgages.

Create a company and hire them to “work” one hour a month for a big salary. If you put $25m in an account, the interest covers the salary. They get a steady bonus income with the added bonus of getting the best insurance available. Is that legal?

Not sure on the legality, I guess you’re essentially creating some sort of shell company? Keep in mind both the company and the “employees” will be facing taxes. Those “employees” are going to end up in entirely new tax brackets depending how high you bumped their yearly incomes.

On the upside they would be paying way, way more into social security so at least they’ll end up with a bit more coming back in their later years if social security still exists. And you could maybe do things like auto-enroll them into a 401k and invest that into retirement savings… as long as each “employee” doesn’t somehow screw that up since each 401k account is technically their own and you can’t force your will on people to do things with their own money.

Set up a “shared” checking account they can use to pay for…whatever. But would these expenses count towards the gift tax? I do not know.

Not sure on that one but I suspect that’s just another version of gift tax like you said. You’d better talk to a financial advisor.

Buy houses and let them live there rent-free. I don’t really like this one because I don’t want to be a lord to my friends and family.

The smart ones will immediately sell, even if they sell at a loss they’ll make free money. The less smart ones will come back to you ever few years when something needs to be done with the house, it’s very possible many of those people will be living in houses they can’t actually afford to maintain and upkeep and you put them in that situation in the first place…

I’ve wondered the same. I previously planned (if i won the big lottery) to set up a $1 million trust with the idea that my work department could take 4% per year to purchase equipment. I returned to work at the end of the summer this week to find that the idiots who are now in charge threw away over $10k worth of stuff that i (and a bunch of school kids) need. Those fuckers aren’t getting shit now and i hope i win just so i can buy my whole team into retirement and leave the fuckers totally fucked!

Back to the topic - i wonder about setting up some type of grant program. Maybe, as you mentioned, paying things for them instead of giving cash? Do you pay tax when you get a home through habitat for humanity? Can i pay for someone else’s health insurance or fill their hsa account? Maybe a scholarship for their kids? Most people i know would be pretty happy to have $18k each year dropped into their retirement accounts.

Tell your friends they can charge your credit card once a month for “escort service”.

Depending on where they live, maybe they should open up a business in order to do it legally correct.

Re:4:
Make them sign leases that they can terminate at any time, but you cannot. Set the rent at $1 a month. Duration 10 years.
Congrats, you have given away wealth without taxes

Statistically u will be broke or murdered so best off putting it all in monero and sending it to me. Trust me i can spend it better.

I would set up a trust that automatically paid them out periodically. I would start with a relatively low amount, to see if money turned any of them into assholes, and if not I would turn it up. but, don’t tell them that’s what you’re doing. firstly it won’t work if they know you’re watching, secondly, using money to control your friend’s behavior is weird, which is why I don’t like the idea of making them work for it either. you didn’t work for it

hand them cash

I have no answer for this, but it reminded me of this old comment on Reddit.

https://old.reddit.com/r/AskReddit/comments/24vo34/whats_the_happiest_5word_sentence_you_could_hear/chb4v05/

I say to hell with the older folks, the math doesn’t check out.

Gift the 18k to each new baby born in the family, have it invested into a large growth fund. Another option would be to have the baby on payroll and make sure ROTH is maxed out.

18k invested for 60 years with a compounding interest rate of roughly 12.4% goes a long way. That’s just a one time payment.