Bowing 737 Max - two planes had crash before they admitted what had happened. u/GFVeggie6

Sears dominated the mail order industry for over a century with their catalog. In 1993, they decided that mail order was on the decline and discontinued the catalog. Less than a year later, Jeff Bezos would found Amazon. u/BlueRFR3100

There was a diet product called "Ayds" before the sound-alike disease. Not at all a blunder, but an unforeseeable, unrecoverable disaster. u/artwells

Gerald Ratner calling his own company’s (jeweller) products “crap” and saying that “a prawn sandwich would last longer” than their earrings at a conference. The company’s value fell by £500m and he had to resign. u/Onion_Heart

Blackberry thinking that they are the top in the mobile market so they didn't need to innovate to compete with those new iPhone things from Apple. u/TechyDad

Supposedly years ago, there was a Pepsi slogan "Come Alive with Pepsi" that was mistranslated in Chinese as "Pepsi Brings Your Ancestors Back from the Dead." u/xain_the_idiot

Back in the 90s Hormel Foods went on a Cease & Desist spree against anyone who was making jokes about Spam because they felt the brand had been damaged and needed to be rebuilt. The last straw was when they threatened to sue Jim Henson Studios over the character Spa'am in Muppet Treasure Island. That turned people against them pretty quick. It turns out if you want to rebuild your brand in the public eye, suing one of the most beloved entertainment franchise of two generations was a bad way to go about it. Eventually the dropped all the C&D stuff and changed their marketing strategy, instead deciding to lean into it and proclaiming that there are always going to be jokes about Spam so they might as well be in on them. u/weirdoldhobo1978

Target's expansion into Canada. Collapsed in 2 years and cost 7 billion. u/USSMarauder

Here’s one happening right now: HBO is rebranding as “Max”. HBO is a premium brand with decades of quality programming behind it. Max is generic, vague, and makes me think of soft core porn. u/watchingsongsDL

Digiorno trying to make the hashtag "Why I Stayed" be about making pizza at home. u/kira82

Celebrities singing “imagine” at the beginning of the pandemic. u/KickiMinaj

Osborne Computer Company in 1981 has one of the first home computers on the market, it sounds fantastic and everything. At the launch, CEO says the next version will be so much better.... So everyone decided why buy this version if the next version will be better? We'll wait for V2.u/BillyBrooks

The BP Deepwater Horizon oil rig explosion was pretty bad on many levels. One of the largest environmental disasters in history. u/ThereWasOnceADJ

One of the movie directors for the Flash movie basically said " This movie will be so AMAZING you'll forget about all the things Ezra Miller did." u/Ex_Fact

Wizards of the Coast and the open gaming license earlier this year. Worst handling ive seen. Literally caused dozens if not hundreds of companies to pull away from creating content for the company to making new games that will directly compete with them while alienating their fans at the same time. u/Konocti

The Ford Pinto's propensity to explode when rear-ended. And Ford making the business decision not to recall because their "cost benefit analysis" showed that lawsuits for injury would be cheaper. u/Hemenucha

Nokia, once the biggest phone company in the world, failed to move with the times and switch to Android/smartphones. u/bent_eye

Xbox One's E3(?) announcement. It was basically a TV box, hardly any mention of video games, and who could forget the infamous "fortunately, we have a product for people who aren't able to get some form of connectivity, it's called Xbox 360." u/A_Wild_velociFaptor

I still remember when Dr. Pepper thought they could a) market a specifically 10 calorie soda and b) do so with the slogan "It's Not For Women" I mean this was 2011, the idea of feminism and antisexism was by no means obscure or fringe. The whole marketing campaign was so bizarre I wonder how on earth a large marketing team looked at blatant, unapologetic sexism and went "yeah sounds great this will sell us lots of soda for sure" u/Donteventrytomakeme

JC Penney tried to eliminate the tons of sales and never-ending discounts on their products by just pricing them at what they would normally be, aiming for a “fair and square” price model. Instead of marking a shirt up to $10 and then having it basically always 40% off, they just priced it at $6, for example. They also ended their prices in solid dollars instead of $0.99 intervals to make it easier to calculate. No coupons, no sales, but the same price. People always complain about how stuff gets marked up just to get put on sale and how cheap of a gimmick it is, right? Well turns out people actually love feeling like they’re getting a deal even if they objectively know it’s just set dressing, and JCP lost millions from the strategy and their sales dropped by around a third. u/soulreaverdan