After Turner Broadcasting merged with Time Warner, they had an opportunity to join forces with Microsoft (Before it was the Microsoft it is today). Ted Turner was heavily in favor of this.
Against Turner's wishes, however, the Brass at Time Warner decided that AOL was a better choice. Ted Turner fought this, and was eventually forced out of the company he built.
AOL Time Warner, as it became known, was a disaster. AOL sucked the money and life out of the business until Time Warner eventually dropped the AOL name, Bill Gates went on to become Bill Gates, and AOL became... wait- what is AOL?
One that personally impacted me and caused quite a few of the supermarkets in the area to close was by Pathmark (might be local to the northeastern US, not sure).
I worked there during a "triple coupon" event. It lasted all weekend, and as you can imagine, a $1.00 coupon = $3.00 coupon.
Thing is, most items that had coupons were between $2.49 and $2.99, so we would frequently get orders that should have been $40 or higher that cost people absolutely nothing. And despite being limit x amount of coupons per customer, they'd just come back in 10 minutes later, send their family in, or just completely ignore that rule in other ways.
Also, the coupons, when they became free, had to be manually entered. Some didn't work. Most were expired but it was too hectic for us cashiers to actually check that. I remember being on self-checkout, which was basically four registers at once, and having to scan every single coupon for the entire shift. It was absolute hell.
The result was that after the weekend, everybody went back to their normal supermarkets, the company lost an insane amount of money, and the employees got to experience the weekend from hell with no compensation for doing so -> a LOT of angry workers.
Sad thing is, they had a few double coupon weekends afterwards that were pretty much the same, ended up cutting the employees' wages with the promise that it would keep Pathmark (at least the one I worked at) open, and then closed it a few months later. Went from being a somewhat tolerable place to work at to being the supermarket equivalent to hell.
I audited an air cargo company, and essentially a member of the legal department had shifted the T&C's on their lease contracts. Basically they re-arranged the terms and in the process of copy+Pasting the information, they unintentionally cut the part out which pushed all the normal flying expenses back onto the client (fuel, landing fees, all the stuff a normal air cargo contract would come with).
The contract was for their biggest client, and for a while, the client signed the papers and paid as they normally have until the client got all new management. The new management at the client reviewed all contract terms and found they no longer had to pay these expenses they previously were.
So they didn't....for two years. When the company I audited found receivables aged greater than two years they began to flip out and demand payment.
The customer basically said, "I have no obligation to pay, so we are not."
The company I audited went back to the agreement where they pretty much said "Oh fuck..."
The receivable was not collectible, so they wrote it off, forcing them to take an enormous hit on their income statement, which in turn caused them to break a debt covenant, and all their long term debt became current. Boom. Dead in the water all due to a copy and paste error.