9. AT&T tried to get into the Cable business: This deal really burned cash. In an ambitious move to try and enter the world of cable TV, AT&T paid $100 billion to buy out TCI (Tele-Communications Inc.) way back in 1998. Unfortunately, AT&T ended up breaking itself up, and selling the cable assets.

8. eBay and Skype: Three words: It didn’t work. This move was on everybody’s list of horrible acquisitions, according to Business Insider, and especially since it limited both companies. Thankfully, Microsoft acquired Skype later on, and since eBay had a 30 percent stake, the sting didn’t last for too long—just for 6 years (eBay bought Skype in 2005, and Microsoft acquired it in 2011).