Vince McMahon has owned World Wrestling Entertainment since the 1980s, and in doing so, he’s proudly become a certified billionaire. He and his family have collectively profited more from professional wrestling than any other people, and they’ve built the empire to prove it. In addition to WWE itself, Vince, his wife Linda, and his children Shane and Stephanie collectively own dozens of incredible possessions, with Vince owning the biggest and best items as would be expected.
The most expensive things the McMahons own aren’t atypical to billionaire family, i.e. mansions, personal jets, and countless vehicles. Given Vince and his family’s well known eccentricities, there are also a handful of completely bizarre but nonetheless extravagant pieces of memorabilia. On top of that, Vince also owns almost all of professional wrestling history in video form, and he’s owned a few non-wrestling ventures that cost him a pretty penny, as well. The fact they tended not to pan out made them even more expensive in retrospect.
Outside of the wrestling dynasty, Linda McMahon was recently appointed to head the Small Business Administration under the upcoming Donald Trump Presidency. Especially now that she’s poised to hold this position of economic power, it’s fair for citizens of the United States to question what she and her family do with their fortune. It’s also worth mentioning that one way or another every fan of the WWE Universe has contributed to the McMahon family fortune. If you want to know where your money’s been going, keep reading to learn about the 15 most expensive things ever owned by the McMahon family.
15 Fleets Of Personal Vehicles
Although Vince and the McMahons are like most billionaires in that they handle most of their travel via airplane, they also need to own cars and/or other vehicles to get around in their every day lives. Granted, they probably don’t need multiple cars each, but it shouldn’t be a surprise they’ve used their wealth to buy two or three cars per McMahon. Vince himself owns at least three cars that we know of, most expensive of which being the $190,000 Bentley Continental Coupe. McMahon’s Bentley was actually briefly stolen in 2015, and upon discovery it was released that on top of the huge price tag the car itself holds, Vince also decked it out with a $100,000 sound system. Vince and Linda additionally own a Volvo station wagon, a GMC Yukon, a Jeep Grand Cherokee, Mercedes-Benz SLR 600, and a Boss Hoss motorcycle. Shane and Stephanie’s current rides aren’t public knowledge, but it was at one point reported Stephanie owned a Porsche convertible and that Shane was a fan of BMWs.
14 WWE Niagara Falls
Predating the pop-up store concept by a full year, WWE created the only company specific merchandise outlet in early 2002 with WWE Niagara Falls. The exactly price and value of this property was unclear, but it goes without saying that prime real estate on the Clifton Hills strip in Niagara Falls doesn’t come cheap. WWE Niagara Falls was in business for the better part of 9 years, closing in March of 2011. As one would expect, the store mostly sold t-shirts, DVDs, autographs and other memorabilia related to the McMahon wrestling empire. It also contained a standalone drop tower ride called The Piledriver, and top WWE wrestler theme music played throughout the building at all times. Though not successful enough to last, or even receive much publicity in the United States, the shop was relevant enough to Niagara Falls tourism that local hotels would constantly advertise it on hotel televisions. The final autograph signing took place in October of 2009, with fan interest constantly decreasing to the point no one noticed when it went of business.
13 WWE Stock
Of all the extravagant things this list will cover, the most valuable possession of the McMahon family is the company on which they built their fortune, World Wrestling Entertainment. Vince and Linda purchased the company from Vince McMahon, Sr. and his silent partners Gorilla Monsoon and Arnold Skaaland in 1982, and the McMahon family has remained the majority owners of the company since it went public in 1999. In May of 2013, Vince sold millions of dollars worth of stock to Stephanie and Triple H, but still remained the majority shareholder with 48.8% ownership of his company. Shane, Stephanie, and Triple H collectively own about 5%, keeping the McMahon family firmly above the halfway mark and meaning their vote will always be final in making company decisions. This also only concerns Class A stock, and the family also owns 90% of Class B stock, making them more than majority owners. The exact price and value of this stock has raised and lowered somewhat since going public, but as of 2016 it’s still more than enough to make Vince a billionaire. Should the WWE Network become as profitable as he hopes, the stock will only continue to increase in value and allow more purchases like the ones on the rest of our list.
12 The WCW/NWA Video Library
Outside of the personal satisfaction factor, Vince McMahon was pulling off an absolute steal when he purchased his competition in 2001, buying the remnants of World Championship Wrestling. Along with WCW came a gigantic video library dating back to the territorial days of the NWA, though the exact specifics of what videos are even still in existence remains somewhat murky. Despite the potential for profit off these tapes thanks to the WWE Network and other types of home video, Vince was able to purchase the entirety of WCW and its remaining assets for the low price of $2.2 million plus minor legal fees. At the time, WCW was losing in the neighborhood of $80 million per year, so it could be argued that the brand was worth even less than Vince was getting it for. On the other hand, Vince was just about the only person who could profit from the sale due to his status in the wrestling world. Profit he has, and likely will continue to as long as more WCW and NWA footage is released to the WWE Network.
11 Shane's Tribeca Penthouse
Unlike the rest of his family, Shane McMahon largely stayed out of the spotlight from his 2009 departure from WWE until his 2016 return to the family business. Because of this, we’re not entirely sure where Shane lives today, but we do know he left his last publicly disclosed residence in 2014 amidst serious issues with building management. Shane, his wife Marissa, and their three children lived at a condo in the Cobblestone Lofts in the expensive Tribeca neighborhood in New York City. The penthouse cost a reported $3.9 million when McMahon and his wife purchased it, but they left in May 2012 when amidst claims “certain toxic, airborne chemicals” were causing serious health problems to the McMahons and especially their young children. Shane and Marissa sued the building and the Andrews Organization that owns it upon their exit, arguing they were forced to evacuate and lost upwards of $5 million in damages due to the airborne chemicals. Regardless of the structural damage and the fact it might not cost much right now, Shane’s condo was at one point amongst the highest value properties the McMahons owned. However, he never owned anything quite like his sister’s mansion…
10 Stephanie and Triple H's Mansion
Following in her father’s footsteps as always, Stephanie McMahon and her husband Triple H live in Weston, Connecticut, about 20 miles away from Vince and Linda’s primary Greenwich mansion. The home has at least 6-8 bedrooms, an outdoor swimming pool, an indoor sauna, and a giant personal gym. The home is also decked out with a top of the line security system, designed to keep Triple H, Stephanie, and their three daughters safe everywhere in their massive home. The family also owns a smaller property somewhere in Manhattan. It shouldn’t be too surprising for fans to hear Stephanie and her husband live so close to Vince, as they have increasingly seemed like the ones poised to take over the company when Vince is finally ready to let go. They’ve also typically been the ones to purchase stock from Vince whenever he sells his, making their personal wealth inch ever closer to his. The exact cost of her mansion is unknown, though it definitely isn’t a coincidence Stephanie cashed in around $9 million worth of stock the year she and her husband purchased it.
9 Vince and Linda's Mansion
Now that the kids are out of the way, let’s focus on the biggest piece of land connected to the McMahon family, Vince and Linda’s Greenwich, Connecticut mansion. The 10-acre 7-bedroom, 7-bath property contains two dwellings, a main house and a standalone apartment above their garage. It also contains a gated outdoor pool and massive gym, just like Stephanie and Triple H’s mansion. The property is part of the highly affluent Conyers Farm development, and was purchased in Linda’s name, in order to qualify her for the unsuccessful 2010 and 2012 Senate campaigns. The property has been assessed as worth anywhere from $11.8 to upwards of $40 million when considering all assets included within it. Vince has long been at odds with his wife’s desire to live in a highly affluent Connecticut community, feeling it contradicted his poor upbringing and desire to run a family business. His ire towards so-called Connecticut bluebloods was coincidentally exhibited in a highly public fashion through the original character of his future son-in-law, then called Hunter Hearst Helmsley.
8 Multiple Condos and Vacation Homes
Most people would probably think one gigantic home is enough for two senior citizens, billionaires or not. The McMahons are clearly not most people, though, which is why the Conyers Farm mansion is one of only three properties said to belong to Vince and Linda. Less than 15 minutes away from their main mansion in Greenwich, the two also own a $12 million condo in Stamford. Uncoincidentally, the property is located in Trump Parc Stamford, meaning the building itself is owned by Linda’s eventual boss, Donald Trump. Linda and Vince also own a third residence, a Boca Raton, Florida vacation home worth somewhere in the neighborhood of $2 million. The McMahons are hardly the only millionaire family to own a vacation home in Florida, allegedly having chosen the location due to Vince’s desire to own an oceanfront property. There’s also the issue of one of his other favorite possessions, which this list will soon cover.
7 Debbie Reynolds' Hollywood Hotel
Even amidst the big and bombastic properties owned and advertised by WWE, the Debbie Reynolds’ Hollywood Hotel & Casino in Las Vegas seems exceptionally out of place. Whether it makes immediate sense or not, WWE most definitely purchased the hotel from Reynolds in 1998. Reynolds, a former movie star most famous for her lead role in Singin’ in the Rain, had purchased the hotel in 1992. Her plan to turn it into a casino focused on her personal collection of memorabilia was a complete bust, forcing her to sell in the late ‘90s. WWE purchased the property for $10.65 million, reportedly with the plan of demolishing it and replacing the space with a 35-story wrestling themed casino. The site was stripped of any remnants of the Debbie Reynolds years and even briefly operated as the Convention Center Drive Hotel while WWE still owned it, but plans to create a wrestling casino were ultimately scrapped entirely in under two years. Despite how historically unsuccessful the area was, WWE was able to sell the property to the Mark IV Realty Group for $11.2 million, more than a half million dollars more than they purchased it for.
6 The XFL
Vince McMahon’s failed venture in professional football was a complete failure in every way his dominance over professional wrestling was a success. The problems with X Football League should be evident immediately upon learning the X in the title actually stood for X, a blatant microcosm of how poorly thought out every element of the venture was. The XFL was announced in 1999, broadcast it’s sole season of play in 2001, and closed it’s doors later that year, with Vince McMahon himself later admitting the ordeal was a “colossal failure.” He wasn’t the only one to lose out on the deal, as NBC suffered equal culpability, both reporting $35 million in losses. Initially, Vince and NBC had spent $100 million each on the endeavor, only recuperating 30% of their investment by the time things were over. Though most XFL games were broadcast on NBC and affiliates, the WWE half of the deal was arguably far more important to things falling apart. Vince himself was all over the product, something that made fans skeptical the entire league was as scripted as wrestling.
5 The Cape Cod Coliseum
Three years before he officially purchased WWE from his father, Vince McMahon actually first attempted his hand at owning a hockey franchise, namely the Cape Cod Buccaneers. The team went out of business rather quickly, but in creating it, what Vince was actually doing was making a home team for his Cape Cod Coliseum. Vince purchased the Coliseum in 1979, leading the McMahons to join the International Association of Arena Managers and learning the ins and outs of management. Linda later called the endeavor a “great benefit” to the future success of WWE, largely because of the connections made with other arena managers at IAAM conferences. The property was valued at around $2.5 million throughout the period the McMahons owned it, an equivalent to more than $8 million today when considering inflation. While one may expect the Coliseum primarily produced wrestling and hockey in line with Vince’s other business ventures at the time, but in fact, the venue was almost exclusively known for high profile rock concerts, performed by names like George Harrison, Elvis Costello, and Van Halen.
4 WWF New York/The World
While WWE Niagara Falls was the only ever standalone WWE store, it wasn’t the only place fans could go to purchase exclusive WWE merchandise in a friendly environment. Three years earlier, in 1999, the company also purchased a restaurant in Times Square they later renamed WWF New York. When the company changed its name to WWE, the name of the restaurant likewise changed to The World. Regardless of what they called the place, it was prime real estate in the Paramount Theater building in Times Square, which doesn’t come cheap in the slightest. Most reports from people who visited the restaurant would attest the Times Square location was as important to the restaurant as the WWE name, especially when the outrageous prices were concerned. Though WWF New York/The World was allegedly quite popular during WWE broadcasts, the cost of property in New York City was so high the restaurant rarely made a profit. WWE ceased operation of The World in 2003 and later sold it to the Hard Rock Café in 2005.
3 The WWE Corporate Jet
Considering how much travel billionaires like Vince McMahon do, coupled with his nonstop cross country flights to attend every Raw, SmackDown, and WWE Pay-Per-View, it almost seems like it would be too expensive for his family not to own their own private jet. That doesn’t mean the one they’ve chosen isn’t as extravagant as you would expect, costing an approximate $33 million after certain “improvements” the company made to the already $27 million aircraft. WWE purchased the 2007 Bombardier Global 5000 in 2013, replacing a nearly 20-year old Canadair Challenger the company had been using since 2001. The company has also floated plans to make the jet available for private charter, allowing rich enough fans the chance to occasionally fly with their favorite superstars. Typically, though, the people riding on the plane are Vince and his closest confidants, including his family, advisors like Pat Patterson and Michael Hayes, and executive producer Kevin Dunn. Top wrestlers in the company have also earned the chance to ride with the boss in his plane, which also includes a sound-proof office and full Internet access.
2 The Sexy B----
We mentioned earlier that the McMahons own their oceanfront Florida property in part so Vince has a place to dock one of his most valuable possessions. Considering the man owns a fleet of cars and his own plane, that he also owns a private yacht only feels natural. Knowing Vince the way his fans do, it also feels bizarrely appropriate that he would name his 47-ft. ocean liner “The Sexy B*tch.” The McMahon family boat’s name came under fire in 2010 during Linda’s first run for the Connecticut Senate, when pundits argued using the word “bitch” was in and of itself misogynistic. The strange part of that story is that the McMahons have owned The Sexy Bitch for decades, and no fan of pro wrestling was particularly surprised with the information. Outside of knowing it existed, however, not much about The Sexy Bitch is known, aside from the fact Vince obviously loves it considering he bought a third home just so he could store it somewhere special.
1 An Actual Tyrannosaurus Rex Skull
After all the normal and understandable properties and possessions owned by the McMahon family out of the way, we’re capping off this list with something only an eccentric billionaire like Vince would ever even considering purchasing. Proudly on display in the WWE corporate office, McMahon owns the actual skeletal remains of a Tyrannosaurus rex. Technically, Vince only owns the skull, but that’s significantly more dinosaur than anyone else we’re aware of ever purchasing for personal use. The T. rex skull was actually a gift to Vince from Triple H, around the time the latter was filming The Chaperone. The skull was originally featured as a prop in the film. McMahon tweeted an image of his T. rex in 2013, explaining that it was “symbolic of [his] voracious appetite for life.” Someone in WWE even gave the prehistoric remains a name, Stan T. Rex. Honestly, we have no idea how much something like this costs, and it might not quite compare to some of the family mansions or sports cars. Nonetheless, part of a dinosaur is such a weird and specific purchase it better defines the McMahon fortune than any of their material possessions, and in that sense is completely invaluable.
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