Every Single Time Homer Simpson Loses BIG Money

Every Time Homer Simpson Lost BIG Money

Some things in life are set in stone. The Earth rotates around the sun; the tides ebb and flow; and “The Simpsons” will always be on TV somewhere. And, at the heart of it all, there is but one man.

A role model for his kids? Husband of the year? Employee of the month? Not exactly. Homer’s heart is usually in the right place, but his brain? And that means that when it comes to money, he’s had some questionable moments.

So, just how much has he lost (or missed out on) over the years? Let’s find out!

Starting as he clearly meant to go on, Homer’s first brush with financial ruin actually comes in the show’s first episode. Christmas is almost derailed when a) Homer’s holiday bonus gets canceled, b) Marge spends the family’s emergency fund paying to remove a tattoo from Bart, and c) in desperation Homer loses the $13 he makes as a shopping mall Santa by betting on a 99-to-1 huge outsider at the dog track. That losing bet does soon become the ever-loyal family pet, Santa’s Little Helper… but in the meantime Homer’s trend for losing money is up and running. Including the unspecified missed bonus, he’s already down thousands. But we’ll start slow and only mark the loss of his Saint Nick paycheck. Just to get the ball rolling.

Into season two and the stakes are suddenly a lot higher. The setup, Bart’s skating through town when he’s hit by none other than Springfield’s richest man, Mr Burns. Initially, Burns offers up $100 on the quiet, at work… but the situation escalates until he and Homer end up in front of a judge. Burns then tries to settle out of court, and here’s where Homer loses big. With the Simpsons initially seeking one million, Burns offers half at 500,000. Homer rejects, Burns learns of some creative case-building in the process… and our man lands up with nothing. The tension is even enough to threaten Homer and Marge’s marriage at one stage. But they pull through, even if their bank balance doesn’t.

Onward to season three, and Homer manages to bizarrely miss out on the same astronomical amount again. In the episode, “Flaming Moes”, it’s the bartender who’s initially down on his luck. But then Homer cuts him into a secret recipe for a flaming drink that quickly saves the bar. Only problem is, Moe takes all the credit, and he and Homer fall out… a situation that eventually plunges Homer into some low-level insanity. Eventually, Moe’s persuaded to sell the recipe and split the million dollar price with Homer. And it could’ve been oh so lucrative… it’s just that right then s when Homer snaps and reveals all for free. And like that, we’re into seven figures.

Next comes another so-near-but-yet-so-far moment. And, while Marge is really at the heart of it, the hurt of lost money is by no means lost on Homer. In season three’s “Dog of Death”, Santa’s Little Helper falls ill and his treatment forces the Simpsons to cut back. Which, for Marge, means no more weekly lottery ticket. Homer’s already depressed enough after not winning the previous jackpot, but it gets worse when Marge’s one skipped draw turns out to be the one time she would’ve won. Consider that it’s in this story that we also get to see exactly how Homer would spend if he were ever rich, and you gotta really feel for him.

In and around this early-90s era for the Simpsons, and we have plenty more notable money fails. First, there’s when Homer sold his shares in the power plant just too early. He pockets $25 to spend on beer, yes… but he could’ve bagged $5,200 if only he’d waited it out. Marge had a savings account planned, but c'est la vie.

Then there’s when Homer might’ve sued Burns for millions, on account of nuclear-plant-triggered infertility. But, instead, he settles for a two grand check - and an impromptu (but worthless) award). He then almost loses the two thousand by investing in his brother, Herb… but that’s another story. There’s no specified amount here, so we’ll go easy and add only a single million to the count.

Just a few short episodes later, and Bart chooses an elephant over $10,000 after winning a radio phone-in. Homer tries (and fails) to convince him to go with the cash, so it’s only fair we chalk this one up too. Then he manages to lose a load more cash on said elephant. So, that’s going on as well. There’s brief mention of plundered thousands, but we’ll stick with the less (but more definite) number calculated in this hilarious scene:

Next, and there’s a somewhat hazy moment for our purposes when, in “Burns’ Heir”, Homer really does sign away his own son so that Bart can inherit Burns’ untold fortune. It’s hazy here because a) the inheritance that Bart eventually gives up is more his loss than Homer’s, and b) Burns’ fortune is never explicitly revealed in this case. Oh, and c) despite Bart eventually turning on his would-be mentor and sending him through the open trapdoor, we never actually see that contract from earlier get revoked. So, you never know, perhaps Bart is still Burns’ heir after all. Either way, it’s another important moment in the money-losing character-building of Homer Jay, but we’ll leave it off his total this time around.

Now, though, and what’s clearly beyond doubt is that Homer does not know a bargain when he finds one. In terms of episode running order, this moment comes shortly before both when Bart gets an elephant and when he almost pockets the Burns fortune. It’s a side gag but a costly one, when, during a neighborhood swap meet, Homer goes rummaging in an “5 cents each” box. So, what did we have there?

A seemingly first draft of the US constitution; known to have sold for $43.2 million before now. An apparently first edition of Action Comics 1; known to have sold for $3.2 million before now. An entire sheet of Inverted Jenny postage stamps; at even the lower estimate, they sell for upwards of one million per stamp, and Homer passes on thirty-five of them. And a Stradivarius violin; which, condition and provenance-dependent, values at $15 million or more.

So, that’s almost 100 million in one cardboard box, and now we’re really rackin’ it up. How about some sugar to take the edge off? Near the start of season six, and that’s Homer’s next great scheme, at least. For the briefest of moments his questionable expediency leads him to become a full-time sugar baron. It’s the kind of business that could only make sense to Homer, and ultimately it’s an investment that comes back to haunt him… when he comes oh-so-close to a $2,000 payoff, only for a storm to break and his chance to disappear.

Homer’s hard luck with foodstuffs continues later in season six, when a mistimed buy-up of pumpkins lands him needing to do the unthinkable and borrow money from Patty and Selma. In this case, the issue is eventually sidestepped without any serious or long-lasting financial hit, and Homer’s rocky relationship with his wife’s sisters just about remains in one piece. The total remains untouched, although Homer’s dignity does take another beating.

We’re now well into the mid-to-late 90s in terms of air date, and thankfully Homer’s money issues do seem to briefly slow down. Yes, there’s that time he parts with more than $10 million worth of prize greyhound puppies for free… and, true, the Simpson family as a whole missed out when Grandpa and Bart couldn’t quite keep hold of the Hellfish cache of lost art… and then Bart and Lisa also had that brief brush with a briefcase stuffed with banknotes, all of which were eventually lost into a dam. But, for the most part Homer manages to more or less keep it together.

That is until the living nightmare that is (and was) Little Lisa’s Recycling Plant. Once again Mr Burns is at the heart of the story, when he forms an unlikely partnership with Lisa, who believes that he’s a changed man. But, of course, he isn’t. The Recycling Plant is actually the opposite of what it should be, but Burns uses it to get rich anyway. Most memorably, though, he sells it for $12 million, and offers Lisa ten percent. Lisa turns it down for the sake of her morals, causing Homer to literally almost die. And the real kicker comes right at the end.

What’s truly shocking, however, is that we haven’t even arrived at Homer’s two largest losses yet. They’re incoming, but let’s just clear up some more of the smaller stuff beforehand. Let’s see, there’s the $15,000 of charitable donations that he goes and blows on an overpriced car just to crash it into an icy lake at Christmas. Plus the failed grease business that he and Bart try to hatch. No confirmed major losses, besides again with the dignity. And not forgetting all that unspecified cash he blew when he briefly thought he was fated to die soon.

But, again, all of that is really just fluff before the main event. The second-most and most that this lovable fool has ever thrown away. First, we’ve come to Tomacco. In an iconic piece of trademark financial foolhardiness, Homer stumbles across what could be a miracle crop - the bitter but addictive blend of tomatoes and tobacco; tomacco. The setup? He’s hiding out at his family’s old farm on account of him having to flee from a pistols-at-dawn duel. As you do. And, despite all the flimsy morality of tomacco, it very nearly makes the Simpsons rich. That is until greed gets the better of them, Homer demands 150 billion instead, the deal falls apart, and some dangerously addicted farmyard animals destroy the plant that started it all. There’s a lesson to be learnt here, but for now all that matters is a massive climb on the counter.

But wait. There’s still an even bigger hit to come, with Homer’s greatest loss of cash of all. Because, in an episode that actually aired a couple seasons before the Tomaco catastrophe, “The Trouble with Trillions”, Homer’s taxes land him in big trouble with the government. And, in a bid to get off scot-free, he starts working as an informant for the FBI. One thing leads to another, and before you know it Homer’s in the know about a one-off moment in American financial history. And then he winds up turning against the suits, landing in cahoots with Mr Burns and on the run from law and order… all the way to Cuba. Now, in a fateful meeting with Castro, Homer plays a pivotal part in instantly losing his share of some truly enormous wealth. Adding one third of a trillion dollars onto our number, just like that.

In truth, the losses are never bigger than they were in Cuba. But still, there are plenty more moments easily huge enough for this video. Such as in season fourteen episode five, when injured Homer settles for hockey tickets. And in season fourteen episode eleven, when Homer confesses to having spent all of Bart’s earnings from the time he was a child actor, in order to hush up some incriminating photographs. There’s also when he sunk five grand on poker in Moe’s basement. When a freshly zen Homer cut the power to lose Bart’s share of five hundred grand at a gaming tournament. There were these dubious purchases, which were enough to inspire a bout of money-saving by Marge. And not forgetting the time when Homer’s $10,000 inheritance disappeared after Grandpa got scammed. Or, in the same episode when he fell for a pyramid scheme.

Of course, there are countless smaller losses, too. Like that twenty bucks he lost by slipping on a peanut. The unknown amount sunk into the North American Sumo League. The fistful he lost when the carnies saw him comin’.

The list could go on and on. And so, if there’s one thing that this little deep dive should teach us, it’s ‘don’t watch the Simpsons if you ever need financial advice’. Don’t bet all you have on the greyhounds at Christmas. Try not to invest in an elephant, skip the lottery, over-stock on sugar, or negotiate with Cuba. Do everything that Homer doesn’t, and you might just be OK.

To recap, here’s the final tally. It’s a big number. And remember, some of the unspecified losses have actually been left off. So many of the most chaotic career moves don’t even directly contribute. Homer Simpson, how do you do it?

Over and above everything else, though, the fact remains that, rich or not, Homer is one of the single greatest TV characters of all time. What he lacks in money smarts, he makes up for, well, in this kind of thing. And this. And this. The never-ending quest to line his wallet is just one of the reasons why the entire world loves this guy.