A plot where one non-rich character has a huge and very sudden increase in expendable income. This might be for any reason, such as winning a lottery, inheriting the fortune of a rich friend or a long lost family member, getting a better job, criminal enterprise, inventing the latest popular gadget, or even because something was delivered to the wrong address or a computer glitch suddenly put an extra few zeroes on their bank balance. Simultaneously, however, they are handed the Idiot Ball.
Almost invariably, Acquired Situational Narcissism makes the character start to act like an Upper-Class Twit or Nouveau Riche, spend like there's no tomorrow, mindlessly buy "whatever it is that rich people like", blow off their former friends as has-beens, etc. The Intimidating Revenue Service and distant relatives never heard of before or since may also demand their share of the character's winnings. Within a few days, one of the following happens:
The character somehow manages to completely exhaust their fortune except for just enough to buy themselves back into the life they had before.
The bank, mafia, CIA, etc., realizes their mistake and sends a collection agent to confiscate the missing funds.
They get fired from their new job for gross negligence, making the company look bad, insulting the boss, etc.
They get in trouble for something, and to get out of jail time, a mob hit, etc., they must abandon their fortune.
At that point, the character is sincerely worried about their future and the people they left behind, perhaps for the first time in their life. They are now so low that a life in Perpetual Poverty is starting to look good to them, having insulted their old friends, quit their old job, etc., they are likely on the streets. Expect the character to be Easily Forgiven; their friends blow it off as completely unimportant, their old boss hasn't been able to find anyone willing to apply for their old job, the person they sold their old house to is moving out of the area and sells it back to them, and the collection agents go home. In shows where Status Quo Is God, the episode's end will have the character's lifestyle restored toexactlywhat it had been before. If not, there may be a surprise twist which leaves the character with something after all, perhaps something that couldn't be had for All That Glitters. If a character's life isn't restored at the end, they've gone from Riches to Rags.
Opposite of Broke Episode. Contrast Rags to Riches, where they get to keep the money. Compare Credit Card Plot, in which the character only thinks they've hit the jackpot. See also Taxman Takes The Winnings, when a character's new money all goes to taxes.
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Anime And Manga
Kankichi Ryotsu of Kochikame had been making his fortunes multiple times throughout the series whether from inheritance, gambling or selling popular products. He always lose all his wealth from overspending, bad investments or from accidents. He's back to being a patrol officer again.
In One Piece's Water-7 Arc, it's implied that, prior to stealing the Straw Hats' two million, whenever the Franky Family got into some cash they'd lose it either through partying or betting at the races.
In Tactics, whenever Kantarou and thus, the gang, come into any money, it's guaranteed never to last very long, much to Youko's despair.
Faye from Cowboy Bebop has this as a recurring problem. Every time she comes into a good chuck of money (either through swindling or genuine bounty hunting) she'll blow it betting on races and lose it all in an instant. Spike even calls her out on it but she proclaims "Its better then keeping it in the bank."
The Serenity comic book Better Days. It happens to Malcolm Reynolds.
Has happened in Disney Ducks Comic Universe comics multiple times, usually to Donald, sometimes involving his uncle's money (though obviously that isn't usually all lost, or it's lost back to Scrooge). At least once Scrooge even lets him "take care of his business" to have him lose as much money as possible when he realises he himself can't bear to carry out a bet to do so even though that would lead to greater gains.
José Carioca once met a gypsy who predicted he'd get a lot of money but he didn't take it seriously. Eventually, he met two men with what he recognized as a stolen jewel. Knowing the owner's offered a reward, he took it from the "bad guys" and went to the owner's manor, where he got a reward, becoming wealthy. Until the "bad guys" revealed themselves as cops who were about to deliver the jewel back. José had to give it back. The gypsy later told him she'd have told him his wealth wouldn't last long if he had let her finish reading his hand.
Chuck Billy's father once won the lottery. He donated a part to the church and then he was surrounded by people trying to mooch off, including some distant relatives. By the time Chuck and his mother found his Dad, the money that was left was, as Chuck's mother surmised, enough to buy new clothes for the three of them. Chuck's Dad then went back to the place where he got the prize and tried to borrow money for more tickets.
Films — Live-Action
The Jerk. Navin Johson invents a device to hold people's glasses in place and makes millions. He spends like an idiot, then loses everything when the customers sue him because the device made them go cross-eyed. Averted at the end when he moves back home and finds that his family has become wealthy by investing the money he sent them.
Dumb and Dumber: Lloyd has absolutely no financial savvy. Give him a briefcase full of money, and he has even less.
Blank Check: A 12-year-old boy gets and blows a million dollars.
Subverted in Brewster's Millions (in it's many iterations). Everyone thinks this is happening to Brewster, but he's deliberately trying to waste a fortune as part of a condition of his inheritance. It's implied that the condition is there to teach him how quickly a fortune can be lost.
In the movie It Could Happen To You, Charlie's wife Muriel divorces him after he wins four million dollars in the lottery and turns out to have promised half the winnings to a waitress, Yvonne, in lieu of a tip. The divorce lawyers claim the winnings to be the wife's since "he bought the ticket for her," even though the numbers weren't exactly the one's she picked. After getting a hold of both shares, Muriel - dreaming of even more money - marries another "millionaire" who turns out to be a con man who steals the money; she's forced to live with her mother in a small apartment and go back to work at her old job in a nail salon. Charlie and Yvonne end up much better off.
This happens, or has happened, in one character's backstory in Stephen King's The Stand. The pop musician Larry Underwood had one big hit and made lots of money out of it, but soon found that there wasn't that much after all and anyway he'd certainly spent it all partying like an idiot. After the world changes and has to be rebuilt, he never mentions to anyone that he was the guy who made that popular song.
The book, Money Can't Buy Love. Before winning the Maryland Lottery, the heroine is broke, hates her job, and her boyfriend is slow to commit. When she wins, she cheats on her now-fiance with a much younger man, alienates the only two friends she had and quits her job. She also spends foolishly, buying a new car, a mansion, a studio, and a brand-new truck for the younger man. At the end, she loses everything except her car and takes the little money she has left to move to a small town where no one will know her.
In Maskerade, the witch Nanny Ogg writes a book and while not wanting to be treated like , er, royalty, ensures she gets a $5,000 advance for her book from a formerly reluctant publisher who has not encountered irritated witches before. Temporarily, this is the most money she has ever had at one time, but her friend Granny Weatherwax soon ensures it is spent well and responsibly.
Ben Gunn (who is slightly bonkers) squandered his share of the treasure in three weeks.
According to Long John, who got married and opened an inn, every other member of Flint's original crew did this. He gives advice to a new recruit on how not to.
A minor example in Horatio Hornblower occurs at the end of Lieutenant and the beginning of Hotspur. Hornblower and Bush get a hundred pounds each in prize money for the Spanish privateer vessels but spend all of it on the dubious delights of Kingstown. Later, Hornblower wins quite a bit of cash (and more importantly, the respect of officers who can give him a new ship) at whist, but all of that goes for his ill-advised wedding to Maria and completing the Hotspur's commission. He doesn't attain true financial security until he gets a permanent stable salary as Colonel of Marines[[note]]a kind of military honor, not a job description[[/note] and marries Lady Barbara Wellesley after Flying Colours.
In a two part episode of The Bob Newhart Show, Orphan Dentist Dr Jerry Robinson spends a new found fortune to advertise looking for the parents who put him up for adoption.
In The Twilight Zone episode "The Man in the Bottle", a genie grants a shop-keeper and his wife four wishes. One of those wishes is for a million dollars, but they end up with only $5 after giving large sums to their friends and paying taxes to the IRS. Despite the four wishes, the couple ends up in the exact same condition as they were at the beginning of the episode. The husband had wished to lead a country and not be in danger of being voted out of office, so the genie turned him into Adolf Hitler - about to commit suicide at the end of World War II. He used his last wish to undo this one, and he and his wife gained a new appreciation for their modest lifestyle.
In the "Lotto Fever" episode of Cold Case, the victim wins 8 million dollars in the Pennsylvania Lottery. He spends his money foolishly (huge house, race car, go-karts for himself and his friends, etc) but he was still the nice guy everyone remembers, and gave money to his friends and family. Before he was killed by his sister and her husband he had enough money left to move back into his old apartment and was working at his old job again, but not before giving his last $100,000 to the one friend who didn't ask him for anything after he won. She received the money in the Medley Exit.
One episode of Married... with Children has Jefferson finding out that a doll treasured by his wife, Marcy, is worth millions, so he gets a different doll, switches it with the one Marcy owns, and then sells her doll for the fortune without her knowing, while getting Al to pretend to be him on the night he does this in order to prevent Marcy from becoming suspicious, on the promise that Al would get his share upon Jefferson's return. The problem? Jefferson loses the entire fortune at a casino on the way back, meaning Al had just spent a night with a neighbor he abhorred... FOR NOTHING.
While many of the drug deals arranged by the Trailer Park Boys are in fact successful and net a large amount of money, our heroes typically end up quickly spending it or losing it altogether. This means they have to come up with another drug deal in the next season.
Castle had the titular character recall how he acted out this trope when while he was still in college his first book became a bestseller and he became rich overnight. He quickly spent his new fortune on expensive luxuries. Luckily for him his next book also sold really well and he learned to be smarter with his money by then. In the present Castle is portrayed as being quite rich but so practical with money that it does not really show.
Another episode featured a murder victim who won the lottery and then seemed to spend the money on extravagant things as well as giving money away to homeless people. Castle figures out that this was due to guilt over stealing the winning lottery ticket
On Parks and Recreation Jean-Ralphio gets a lot of money which he uses to start Entertainment 720, an entertainment company. He hires Tom to help him and together they spend the money on extremely extravagant gimmicks. They hire two professional basketball player to play one on one all day in their office, give a free iPod to anyone who visits, pay random women $100,000 a year with free medical benefits to do nothing more than sit at desks and look pretty.
Firefly. After the crew knocks over the Ariel hospital, they've got a small fortune in medical supplies. They get to enjoy their wealth for about half an episode before they end up spending most of it to spring Wash from Niska's torture room. The show was cancelled before they managed to fence the Lassiter they acquired in "Trash".
In an episode of The Wonder Years, Paul Pfeiffer's dad takes a risky investment in an oceanfront deal which ends up paying off big, leaving Kevin's dad, who decided not to join in on the investment, jealous. It all goes south in the end when the oceanfront is lost underwater.
Prof. Oglevee on The Parkers is told that he has inherited $10M from his uncle. He moves out of his apartment and into an expensive house in a gated community, passes out hundred dollar bills to everyone on campus, hires bodyguards to keep him away from Nikki (they let her pass because she made them pies), buys custom-made clothes and shoes, as well as two very expensive cars plus another one for his new girlfriend Paris. He also makes a lot of other expensive purchases. And this is all BEFORE he received one cent from his uncle's estate. In the end, the estate is hit for back taxes, leaving the Professor with an inheritance of ONLY ten dollars. Of course he's broke and homeless, and Nikki is more than happy to help him out.
Season 2 of 2 Broke Girls lampshades the fact that even when you try to avert this trope, it can still play out straight. The girls get a large sum of money from their friend Sophie as a loan/investment and use it to finally start their cupcake store. They try to be very frugal with the money, don't spend any of it on personal items and even keep working as waitresses in the diner to pay for rent and food. However, they misjudged their market, their location is not ideal and they make a number of costly mistakes like not buying business insurance. Their business is losing money and they are only saved from bankruptcy because a developer offers to buy out their lease. They barely manage to pay off their debts and are back in the same place financially as they were in the beginning of the series.
In Season 8 of The Office (US), the six dock workers won $950,000 in a collective lottery pool and quit, leaving the Scranton branch without anyone to load shipments. At the end of the season, two of Darryl's workers apply for their jobs back, saying they made a bad investment in an "energy drink for Asian homosexuals."
In Nash Bridges episode "Patriots", Joe gets a side-job for insurance company to do some watchover over some arabian royal prince about to get a heart transplant. Having watched for two days how the said prince indulges in debauchery at the hotel and frequents shady bars, and pays with checks that bounce, Joe dismisses his one million dollar check of gratitude when all is over, going as far as shredding the check to prove his certainty to his SIU colleagues. Immediately, a call from the bank comes asking in what currency Joe would like to claim his money.
Big Time Rush, the boys complain of not getting more money for their hard work which is being frozen in accounts until they reach 21. So Griffin gives them a challenge of giving each $20,000 and not spending it all within 48 hours. Naturally the boys flub it from the word "Go". James buys a snake in order to impress a girl which fails, Carlos hires an assistant and loses his money having to pay his fees, Logan throws away his money tipping people left and right and Kendall, who was trying to be responsible and invest it, accidentally buys a truckload of oranges. The boys just barely manage to get their money back through some last minute contrivances but do learn their lesson by the end of it.
One story arc had Wally win a billion dollars in a lawsuit, and ended with him losing it all in Vegas.
In one Sunday strip, Dilbert wins the lottery and is blindsided with an interview from a reporter who asks him what he wants to say to the world.
Dilbert: Drinks for everybody!
This happens quite a lot in Popeye; whatever big fortune Wimpy, Olive Oyl or the other supporters make in the last adventure, they'll end up losing it due to some bad investment or whatever. Popeye, on the other hand, seems to like his Perpetual Poverty to a degree, and is such a big softy underneath that crusty exterior, that he will just give away his new wealth to the first needy people he sees.
About a billion Amos And Andy episodes involve Andy and/or Kingfish coming across money and then losing all of it by the end of the show.
In the first scene of Peter Schickele's a capella opera Go for Broke, John Q. Public wins the lottery. In the next several scenes, "Taxes," "Charity," "Kin," and "Company at the Bar," he has to part with his winnings. There is a happy ending in the final scene.
Fry discovers he'd left some cash in a forgotten bank account, and the accrued interest has made him fabulously wealthy. When he buys a can of (extinct) anchovies Mom has her boys kidnap him to get his PIN number (1077) so she can steal all his money and be forced to sell the anchovies (which hold the secret to producing a very cheap, but potent, robot oil). She gives up when she learns he doesn't know this, instead intending to eat the anchovies.
Also fulfills the "worse off than before" part: When Fry and co. actually ''do' eat the anchovies, everyone except Fry immediately coughs them up, due to their disgusting taste. Everyone, that is, except Zoidberg. He suffers the opposite effect, since his species is implied to be the reason anchovies went extinct in the first place due to having a strong Horror Hunger for them. Before the episode cuts to black, Zoidberg aggressively yanks Fry toward him, screaming "MORE! MORE!"
Another had the whole nation getting a tax three hundred dollar refund due to Zapp defeating a spider planet and bringing back the riches. The course of the episode sees all the cast wasting it in some form or another (Fry buying a hundred cups of coffee, Bender gets supplies to steal a rare cigar, Farnsworth a temporary stem cell procedure, Amy a talking tattoo, Hermes a walking pair of stilts to impress his son, etc.) save for Zoidberg who, for the first time in his life having more money then ever, tries to "live like a rich person". He gets shot down when his refund is revealed to be peanuts to the social elite. But a fire breaks out at the reception for the spider people's loot, costing Nixon, in addition to the tax break, millions. Zoidberg then spends his money on a small buffet, which he invites everyone to join.
The whole crew nearly got to be rich after Mom's buys out their company and the stock is worth millions. Fry, trying to backpedal after siding with a sleazy fast talker, gives a speech which somehow makes the stock plummet. Its only after being told about the stock does he realize what happened and by then it wouldn't have mattered if they sold the company or not.
Another time, Zoidberg lives richly for a short time by using the Robot Mafia's stolen money, only to lose it all in a Martian casino, due to his poor money managing skills.
What makes this more crazy is that he actually managed to triple his cash on a roulette table twice. Even when being told to walk away, he kept going. Naturally third time wasn't the charm. He actually takes it all in stride since he's so used to being broke, it didn't matter if he was rich or not
In the episode "Ron Millionaire," Ron gets a check for the current royalties he's owed.* For inventing the Naco. Subverted later, in that Ron never spent all the money; his entire fortune is stolen from him by Dr. Drakken because...Ron kept it all in his cargo pants pockets.
Draken, after getting the money and dropping the trope name almost word for word, spends all of it on a laser cannon... which destroys itself.
The episode of Rugrats where Chuckie's dad won ten million dollars in a sweepstakes, but lost it all when he made a bad investment (on Drew's advice).
George invents a new wonder product that brings in lots of cash. They lose it all, not so much because George was an idiot, but because his company's product goes under.
In another episode, George won the lottery. However, a collapse of the economy of Venus caused the value of the prize to decrease considerably before he had a chance to convert it into dollars. When George was told he won, the prize was worth 7.5 million dollars. The collapse caused its worth to be practically nada.
In another, George and Jane win a fortune at the racetrack thanks to some phlebotinum. They get chased by two guys in dark outfits -from the future tax agency.
Ickis went through this on an episode of Aaahh!!! Real Monsters; the monsters' currency is toenails, so he struck it rich by stealing from an eccentric millionaire who saves his toenail clippings. Ickis gets greedy and is nearly caught by the human, who concludes it was all a dream... telling him to clean up his act. Meanwhile, Ickis ends up losing his stash of toenails on his way home.
In an episode of Code Monkeys, the staff borrow against their IPOs and become very wealthy. When they leave their jobs, Gameavision stock plummets, bringing most of the staff to ruin. Except Dave, who invested his new money wisely, but ends up using it to bail out his former co-workers.
Lois' aunt dies, leaving her a beautiful mansion in Newport, RI, along with a bit of money to get her started. Everything seems to be going well, until in a misguided attempt to fit in, Peter bids a ridiculous sum of money on a vase. To be able to pay for it, he sold the mansion, which was valuable enough because it was discovered it used to be a Presidential whorehouse. Peter even kept an old photo of Abe Lincoln to sale so he could buy back his old house (which he had sold to be able to pay for the mansion's hired help) for double the money he got when he sold it.
The season 10 premiere plays this straight. The Griffins win $150M in the lottery. Peter being Peter, immediately quits his job, spends the money on outrageous items, treats his friends like crap, and becomes broke and homeless in a month's time. Everything is back to normal by the end of the episode.
For double irony, the family, sitting homeless on the street, decides their only chance is to try to win the lottery again. Cut to the exact same scene with Lois saying she can't believe they won and lost all that money TWICE. It's never explained how anyone could be rendered completely destitute when many of those outrageous items were made of solid gold. The logical solution is to sell them for scrap gold.
In the Animaniacs episode "Temporary Insanity", Yakko Warner tricked Plotz into signing a check worth zillions. As soon as Yakko showed it to his siblings, Plotz ripped it out.
DuckTales: In one episode, a family that won the lottery moved into a mansion next to Scrooge. By the end of the episode, they spent so much money they had to move back to their old home.
Woody Woodpecker fell victim to this trope when he inherited some money Buzz Buzard decided to con out of him.
However, it was Buzz's turn to fall into the trope in The New Woody Woodpecker Show. Buzz and Woody were on a Scavenger Hunt where incomplete proverbs were the clues to the items they had to find. They were tied when there was only one item left to be found and the clue was "A (space) and his money are soon parted". Claiming to have no idea of how to solve that clue, Woody proposed that he and Buzz shared the money prize. As Buzz was enjoying the money, Woody introduced Buzz to the game's host as the fool to be soon parted from the money.
In "Simpson and Delilah", Homer once bought a hair-growth product that actually worked and it eventually got him a promotion. Homer ignored Marge's advice about saving money for emergencies and it came back to bite him when Bart, while trying to use the product to grow himself a beard, accidentally spilled it out and Homer had no money to buy a new batch before becoming bald again and being demoted back to his old job.
In another episode, Bart pretended to be kidnapped to avoid punishment for sneaking out. When Lisa found out the truth, Homer told her they should keep it a secret because he had already sold the story for a fortune he had already lost. While how he lost is anyone's guess, since we were never given a clue, we can be sure it was out of foolishness, since it's Homer we're talking about.
One episode averts this. Homer wins the lottery, and since Status Quo Is God, the money is quickly spent. However, Homer didn't blow it on foolishness, but instead he spent the money doing nice things for his family. Though a bit twisted as he only did this because he hid the fact he won from his family because he bought the ticket when he should have been with Marge signing for a wedding. In the end it is revealed that Marge wouldn't have cared when she realized he won a million dollars.
Done in The Oblongs when Milo, Biff and Chip find some money in a car they all brought (Milo loan some money). Not surprising they spend it like crazy despite threats from the Mayor and city staff since it was bribe money meant for them. Subverted though as Milo doesn't act any different with his friends and it actully make the boys popular. But they lose it when Milo tosses a sparkler onto the remaining cash pile and burn it all up.
An episode of Garfield and Friends has the titular fat cat winning the lottery after Jon tosses away his lottery ticket. The two and Odie get to live the high life until an interview reveals that Garfield was underage when he won, thus leading to the winnings being voided (despite Jon telling them that he was the one who bought the ticket) and the winner being declared as the interviewer himself.
Wish Kid: Nick used his magic glove to wish his family was wealthy, causing them to win the lottery. As anyone familiar to the series' premise can attest without watching the episode, it was just a matter of time before the wish wore off and they lost the money. Then again, the way they were spending the money, they'd have squandered it all.
In "Save the Tiger", Baloo saves Shere Khan's life, who now owes Baloo a debt. Baloo first asks for a few simple things, before being reminded that Shere Khan is one of the most wealthy and powerful men in the world. Baloo then buys back his plane, isolates most of his friends, and becomes bored with his new wealth and gifts. Eventually Baloo ends up irritating Khan with endless lists of demands; Khan secretly arranges for Baloo to be kidnapped and the ransom equals the amount from selling all the things that Baloo asked from Khan and Higher for Hire. By the end of the episode, Baloo's friends get him back, and Baloo's last request is for the status quo to return.
In "The Balooest of the Blue Bloods", Baloo inherits a mansion and the butler and maid try to kill him so they can inherit it for themselves. The mansion gets repossessed at the end of the episode.
In South Park, Cartman inherits one million dollars and decides to buy an amusement park for himself calling it "Cartmanland", but needs to allow visitors to keep the park maintained and running. This frustrates him so much, he decides to sell the park to its previous owners. He gets his money back, but the IRS took most of his fortune from unpaid taxes and penalties and the rest (more than what he had) for a lawsuit settlement resulting from Kenny's death on one of the rides.
Batman: The Animated Series, "Joker's Millions". Rival gangster King Barlowe inexplicably leaves his entire fortune to the Joker, who's so strapped for cash he doesn't even question it. Only after he's bribed his way to freedom, hired a new Harley and outright thrown money into the streets does he find a Video Will revealing the catch - less than a tenth of what he inherited is real money. Everything else is counterfeit, and he can either face the Intimidating Revenue Service or admit to the world he's been had.
Adventure Time - "Furniture & Meat". After practically hoarding their gold stash gotten from their adventures. Finn and Jake realize they can actually spend it and proceed to do so. Of course anyone who knows these characters know it won't take long to burn through it. And indeed they end up insulting Wildberry Princess who has them arrested, confiscate their gold then melts it and tries to have it poured over them as punishment. After they escape they, their once huge pile is now barren.
All too common in real life. When poor or even middle-class people, after winning the lottery, gaining an inheritance or otherwise coming into a large sum of money, lose it all and are completely broke in a few years or even months. Unlike on TV, there is rarely, if ever, a Reset Button. It's especially common with people who never learned how to handle money, and who are so overwhelmed with the wealth that they feel like they can never spend it all. By the time they learn how wrong they are, they're often worse off than they were to start with.
This sort of thing is so common that they even gave the condition a name: "sudden wealth syndrome". According to the TLC show "The Lottery Changed my Life," around 33% of lottery winners go bankrupt within 5 years.
This also happens to children who may get a large (for them, at least) sum of money for something like a birthday, first communion, quincinera, Bar or Bat mitzvah, confirmation, Graduation, etc, or even if they get a summer job. Their parents may intentionally sit back and let their kid spend all the money, and then pipe in with An Aesop about money management. Zig-zagged in that a) The amount of money is pretty trivial compared to other examples of this trope b) Some parents step in ahead of time.
Professional athletes seem disporportionately susceptible to this trope, moreso if the player came from a poor background - see ESPN's 30 for 30 documentary Broke for details, which opens by quoting a 2009 Sports Illustrated article stating that around 60% of NBA players are broke within five years of leaving the sport and 78% of NFL players are at least in "serious financial trouble" within two years. Usually the culprit is some combination of:
Their unusual annual income structure (they only get paid during the 5-7 months out of the year their sport is in season)
Short career length (the average tenure of a pro athlete is only 3 1/2-6 years - most will be out of work by age 30) and failure to plan beyond it (because most of their income comes so early, their financial strategy needs to be different from other people)
Forgetting about taxes (if they grew up poor, they probably have never had to worry about paying income tax)
Purchasing items of dubious utility (buying a new house is one thing, buying an eight-figure mansion with an eight-car garage is another)
Not understanding having millions is not the same as having infinite money
Their own fame becoming a liability (players' contracts are publically listed so everyone, including unscrupulous agents, con artists and gold diggers, knows you're young, naive, and have tons of money)
The myraid number of injuries their bodies can accumulate (concussions, knee surgeries, etc.) that too often are only given the bare minimum of care needed to properly heal it (if even that - sports is a world where playing hurt is a virtue) because of the immensive competitive pressure to return to the field (if you don't, you've just lost your job and the limelight). Oftentimes these injuries are ignored or downplayed at first since the players are still young and can still play through them, only showing up once retired - all this means very large medical expenses that the player has to pay for the rest of his life.
Inability to turn down friends/family with handouts (Whether for business opportunities that aren't economically sound or just "C'mon, you can spare an ol' pal a thousand!")
A competitive mentality that leads to success on the field but ruin in the checkbook (they have to outspend the other guy right now; he's got an expensive watch so you need one even more expensive, he's "making it rain" at the club with $5 bills so you need to rain down $20's or even $100's). Said competitiveness also makes them more likely to invest in high-risk ventures real estate or their own vanity project/small businesses, convinced they can win against the odds. (A retirement fund with 3% annual returns is practical, but boring).
The documentary Reversal of Fortune involved giving a homeless man $100,000 in cash and seeing what he did with it. It was gone within 6 months, and indeed he wound up in even worse financial shape then he was before.
Pirates were notorious for spending their fortune after a successful raid on booze and prostitutes in a matter of days. This can be justified as their lives were not quite safe. If you have got a lot of money but could die soon, it can be understood that they considered spending it immediately as a better option than risking never being able to use it.
Even if a pirate was in a fiscally-responsible mood there were few things they could do with their plunder aside from blow it all at the nearest port. Few if any banks would deal with a known pirate (though they might deal with privateers) and many pirates operated in parts of the world where there were no banks to begin with. The best they could do with their gold was hide it somewhere, and only one pirate (Captain Kidd) was ever confirmed to have done that.
German actor Klaus Kinski typically starred in a successful movie, then spent all his salary on partying with friends, expensive clothing and 5-star hotels (and drugs), resulting in him becoming broke after a short time. After he had to live in a run-down single-room apartment for a few weeks, he often resorted to phoning his old friend Werner Herzog once again to ask if he had any more film roles available. Rinse and repeat.