WWE is no stranger to throwing away it's cash. As CM Punk once infamously said Vince McMahon is a millionaire who should be a billionaire except for idiotic decisions plaguing WWE throughout the years. You don't have to look far into WWE's history to find plenty of instances of sacks of cash disappearing for the silliest reasons imaginable. Sure, we can see what they were trying for when we suffered through these moments or problems, but it doesn't change the fact they'd have gotten more heat by burning the money instead.
10 McMahon's Million-dollar Mania
In one of the most transparently desperate ratings grabs WWE has ever done Vince promised to call up fans at home during Raw and shovel money at them for watching the show. Not only did it hardly make a dent in the ratings despite the dent to McMahon's wallet, but it also made for terrible television. With Vince suddenly seeming like every bit of his age as we watched him don glasses and fumble with technology, he got Rickroll'd, dropped phone calls, and generally fumbled everything in regards to his faux-gameshow.
9 "Selling The Company" To Donald Trump
This stunt didn't directly cost much money, however, it certainly cost a pretty penny indirectly. In a somewhat hilarious repercussion, WWE stockholders panicked at the sudden onscreen "ownership change" and jettisoned stock en masse. WWE putting out press releases and trying to make the story look legitimate went further than they could've expected. This forced WWE to retract the development in the story and reshuffle their ongoing plans for guest hosts for Raw and have Trump 'sell' Raw back to Vince for a profit.
8 JBL's Un-Retirement Celebration
In recent times fans have lamented WWE's tight purse strings when it comes to pyro. We got so used to every show beginning with a literal bang and wrestlers having spectacular paired fireworks that when it disappeared we felt cheated. This is especially grievous when you remember JBL's massively wasteful display. Spending almost 5 minutes walking around the ring raising his arms to a ludicrous amount of pyro, it must have cost a pretty penny. In the grand scheme of JBL's career, it is just a phenomenal waste.
7 Million Dollar Man
Vince loved the Million Dollar character so much that he specifically invested in Ted Dibiase's spare time to make it legitimate. Vince wanted Ted spending big bucks wherever he went to ensure that nobody questioned the "Million Dollar-ness" of his new top heel. This meant that Ted was buying ridiculous watches, fancy cars and essentially faking a 'Ric Flair' existence on the off chance someone investigated. Not bad work if you can get it, but ultimately fruitless.
6 World's Most Expensive Man
Mark Henry's first WWE contract is forever notable for it's seemingly 'ironclad' state. Mark definitely 'paid off' in his later career, displaying theretofore unseen charisma and promo skills to go along with his beastly stature and power, but for the first decade, he was a bust. Spending years of his contract in 'developmental', losing weight, or being either a blip or embarrassment on the Raw roster surely had WWE accountants wishing they could draw a line through his paychecks. But, for whatever else you can say about Henry, the agent who sorted out his paperwork did an exemplary job.
5 WWE Studios
WWE's forays into Hollywood have a long track record of being a money-sink. With movies that make barely their budget back or worse, and get reviewed about as well as SY-Fy originals not named Sharknado, the entire division bled capital. They've turned this around in recent years, choosing to invest in projects without taking on major creative positions and this has led to better returns. However, initial efforts were a blueprint for failure.
4 All Hiring, No Firing
Surely this situation will reach it's breaking point soon, but as of now, WWE continues to sign anyone and everyone they can get their hands on. Not only are they diligently signing anyone with a name or any notable athlete they think they can fashion into the next Goldberg, but they're also refusing to let people go. People like Neville had to sit out his contract to find his way out, and unsung superstars like Luke Harper are being paid to sit at home, with WWE even extending contracts just to spite them. It's aggressive tactics to fend off new challenges from Japan and AEW, but it costs BIG money to lock people out of the game.
3 Brock Lesnar
The Beast Incarnate learned well from Paul Heyman in his initial WWE foray, and this second time he has exactly the deal he wants. That means that WWE is paying an absolute premium for the 3-time Universal Champion and seeing him rarely at best. Brock Lesnar is no doubt an attraction and his seldom appearance schedule keeps some of that intact, but it doesn't dismiss the sheer monetary amounts laid out for him to do so. Perhaps his retirement from MMA will lessen the impact of his next contract, but considering his mercurial relationship with wrestling, not likely.
2 Political Poorhouse
WWE doesn't do well when it steps into the political realm. Between terrible impersonators, a certain celebrity Hall Of Famer, and Linda McMahon's twin senate runs, WWE often comes out poorer in both funds and fans. That latter example is a truly egregious one. Both times Linda McMahon ventured into senatorial bids WWE suffered. From terrible content downgrades and PG infantile shenanigans, WWE cut off its nose to spite its face. All while throwing millions at ultimately failed bids for power.
1 Sin Cara, Heavy On The Sin
When Triple H first gained enough influence to begin signing high profile wrestlers into WWE, Sin Cara was the big splash he chose to make. That splash was a decidedly ugly belly-flop. At every turn, the man under the mask disappointed. From botching to the point of becoming a meme to being unable to wrestle anyone competently outside of Rey Mysterio, his value was dwarfed by his mammoth paycheck. He also was an injury magnet who wasn't on board with the whole wrestling mantra of 'the show must go on'. When Del Rio stomped him mercilessly as he held his dislocated pinky like it was a gunshot, it was the final nail in his gilded coffin. For the record, current Sin Cara is an underutilized badass.