10. WWF Hotel And Casino
https://www.youtube.com/watch?v=7UJ8Ye6lNT0 In the summer of 1998, WWE found itself the high bidder at a bankruptcy auction for Las Vegas's Debbie Reynolds Hotel and Casino. With WWE gaining popularity (and making money) each and every week, it was a sensible business decision not only could the resort house fans looking for a completely immersive wrestling experience, not only could it contain a theme restaurant, not only could it host wrestling events for tourists in the area... it was a casino. When run properly, those tend to be moneymakers. Before they could start collecting fistfuls of money, though, the McMahon family needed to make some changes. They planned to level the entire building and start from scratch (a concept video created in 1999 and floating around on YouTube has details of what the final product was hoped to be), creating a pro wrestling Xanadu that could be enjoyed by generations of fans. They tore out a large portion of the building's interior, but hit a snag. In the words of WWE spokesman Judd Everhart:
After we bought it, we realized it just wouldn't meet our expectations of being able to provide our brand of entertainment on the right scale, so we decided to sell it. We have no immediate plans to purchase other property in Las Vegas, but I couldn't rule that out.
Was the property too small, or was this merely a cover story? Either way, at the end of 2000, WWE sold the property for a profit that's right, they actually made money on the venture, making the whole thing (even the egg on the McMahons' faces) worth it. The next time someone says Vince McMahon can't do anything put promote wrestling, make sure to mention that he's a halfway-decent casino flipper.
Final Tally: $1 million profit