Regardless of what you do for a living, it helps to have friends in high places. Even a low level employee can find themselves benefitting enormously from becoming pals with the boss, and in no medium has this been more clear than the always wild world of professional wrestling. WWE has been described as Vince McMahon’s personal toy box on more than one occasion, and since his toys are real live people, he tends to give the best jobs to the ones he likes the best. The same holds true for pretty much everybody in his family, and that becomes truer with each passing day as it seems like Triple H and Stephanie McMahon will one day take over the company.
While being best buds with the McMahon family isn’t essential for becoming a successful wrestler, the careers of quite a few of the superstars you’re about to read about prove that it certainly can help in a major way. A select few of these wrestlers actually weren’t extremely successful, but they still managed to have lucrative and long lasting careers thanks to their constant and sincere connection with the boss. Oddly, the people who were friends with Shane and Stephanie’s jobs usually weren’t that secure, but chalk it up to Vince being a classical patriarch and making the final decisions on who his kids get to hang out with. Find out who benefitted, and learn the strange ways some people ended up getting hurt through their companionships, with our list of 15 wrestlers you didn’t know were extremely close friends with the McMahon family.
15. The Wild Samoans Have Surprising Sway Over Vince
The Wild Samoans, Afa and Sika, are a legendary and infamous tag team in WWE history and pro wrestling history in general. As their name would imply, the two essentially started the concept of a perhaps insensitive, no doubt at least a little derivative Samoan savage, with wild unkempt hair, intense brawling offenses, and strangely indestructible foreheads. Afa and Sika are also famous for their huge extended family that has for decades played an integral role in WWE. Afa and Sika sit at the top of the family, which also includes their children, most of whom became wrestlers, as well. Afa is the father of Samu, Manu, and LA Smooth, while Sika is the father of Rosey and Roman Reigns. The Usos, Rikishi, Umaga, The Tonga Kid, and Yokozuna are nephews of the Wild Samoans, and The Rock is a distant relative, as well.
The fact so many members of the same family would become successes in the same industry actually isn’t that surprising, in that they were reportedly always extremely close-knit, and thus would naturally develop the same interests over time. What is amazing is how much control Afa and Sika still seem to have over WWE to this day, with Sika allegedly loudly complaining when Roman Reigns didn’t win the WWE World Championship at WrestleMania 31, despite Vince McMahon seemingly promising him his son would. People questioned how serious those reports were, but the fact Sika was in attendance both at that WrestleMania and again next year when his son actually did win the gold proves in the very least, the McMahon’s are probably providing the family some free seats.
14. Rodney And Pete Gas Were Really Shane’s Posse
Fans of the Attitude Era no doubt remember Shane McMahon’s character actually made sense at one point, long before he turned into the bizarrely affable and indestructible man of the people he is today. He debuted as an on-screen character in the late 90’s as the spoiled and perhaps a little, shall we say, douchey son of the WWE owner, mimicking his real life situation. Shane also started off as a serious loudmouth, threatening all of the superstars and getting into increasingly dangerous positions, much like he’s still known for today. The difference is that back then, the idea was that Shane was in way over his head and needed some help from his rich kid friends, and that’s where the Mean Street Posse came in.
Pete Gas, Rodney, and Joey Abs were three preppy guys in nice sweaters who would beat up Shane’s enemies and give him all the credit for it. At least Pete Gas and Rodney had years of experience on that front, as they were Shane’s real friends from Connecticut who wanted to become part of the show and get to wrestle with him. While many people on this list used their friendships to achieve great heights in the wrestling world, the Posse merely wanted to get on TV. Shane rewarded them all with quick WWE Hardcore title reigns for their efforts, nonetheless.
13. The Undertaker Only Drops The Act For Vince
With a WWE career spanning 26 years that pretty much always treated him as the ultimate monster in professional wrestling, it’s obvious The Undertaker commands a great deal of respect from the company he calls home. However, fans might not realize just how far that respect goes, insofar as Vince McMahon has on multiple occasions called The Undertaker his all time favorite employee. McMahon cites Taker’s years of loyalty and high quality work for the company as his primary explanation, and though that makes sense, the fact the two have always been pretty close to one another behind the scenes no doubt has helped sway Vince’s opinion, as well.
Vince and The Undertaker weren’t immediate friends when they met, but as the Deadman’s career expanded into one of the most storied in history, he and Vince grew closer and closer until they eventually reached the strong connection they share today. The Undertaker is one of the few wrestlers with the ability to flat out turn McMahon down, but he almost never does anymore, showing just how deep the mutual admiration and respect lies. Also, while Taker is stern and serious about his gimmick and tries never to break character should fans happen to catch him, stories claim he’ll drop the façade to joke around with Vince whenever the two of them come up with a good enough prank.
12. Steve Austin Doesn’t Always Love Vince, But They’re Always Friends
One would be hard pressed to find a long term WWE fan who didn’t know at least part of the long and legendary story that is Austin vs. McMahon. The feud between the WWE Chairman and his top superstar of the Attitude Era, Stone Cold Steve Austin, is part of the reason WWE still exists as the sports entertainment juggernaut that it is today. More people in history wanted to watch Stone Cold beat the hell out of McMahon than they had ever wanted to watch two superstars interact before, and as a result, McMahon and Austin developed a strong personal friendship behind the scenes that lasts to this day. The two of them made so much money with and for each other it’s hard to imagine they’d have any problems with each other, but it’s still hard to reconcile the vitriol they spewed on television with the hugs and respect that followed backstage.
Austin and Vince don’t get along with everything, and Stone Cold is probably the only person on this list who could upset his boss enough to get told to stay off TV for a while. However, we’re confident it wouldn’t be long before Vince apologized and made up with the Rattlesnake, or vice versa, as has happened several times throughout their storied relationship thus far.
11. The Big Show Can Hug All The McMahons At Once
A growing trend you’ll see in this list is that the people who become friends with the McMahon family are generally pretty huge stars, but more important than that, they tend to stick around in WWE for a long, long time. The Big Show certainly qualifies under both of those prerequisites, as he’s been kicking around the company’s main event scene since 1999, and thanks to his size and natural athleticism, could maintain that position for a few years to come still.
The Big Show seems friendly with all the members of the McMahon family, but like many WWE superstars have gone on to claim, he sees Vince McMahon as somewhat of a father figure role. While Big Show spoke with Steve Austin on his podcast in early 2016, the two discussed how important it was to build a relationship with the boss, as Show plainly admitted his long tenure in the company was a result of always trying to make McMahon happy. McMahon, in turn, did well by Big Show and kept him employed and relevant through several decades, despite fans occasionally perhaps wishing that Vince might give the giant some time away from the screen. In the same interview, Show said big opportunities don’t come twice, but his career proved they could—as long as you make the right connections.
10. Triple H Would Hang Out With Vince Regardless Of Who His Wife Was
We figured there was no point including Triple H and Stephanie McMahon on this list, since even the most casual fan of WWE has to know the two are happily married as they sit on their thrones high atop WWE. What fans might not realize, and some traditionalists may even be surprised by, is the fact Triple H is also extremely close friends with Vince McMahon himself, and the two spent a great deal of time together whether Stephanie is hanging around them as well or not. Perhaps it shouldn’t be too surprising since the two are both extremely buff even as Vince reaches old age and Triple H is slowing down in the ring, and the two apparently spend long hours at the gym together bonding as father and son-in-law.
Especially on the Internet, Triple H tends to receive a great deal of criticism for marrying the boss, with people claiming he wouldn’t have achieved any of the success he eventually did were it not for his wife backing him up. The way we see it, even had Shane McMahon been an only child, Hunter would have found some way to endear himself to his boss and work his way into an executive office through hell or high water regardless.
9. Bob Holly Was Given An Extravagant Gift By Vince And Never Forgot It
We mentioned up top that not every wrestler on this list was going to be extremely successful, but we forgive you if it looked like that was just a bluff at first. Proving our point, here is Hardcore Bob Sparky Plug Holly, a wrestler who only barely ever made it above the midcard for short stretches at a time, which generally had fans confused at what the hell he was doing in such important matches. Holly is a former multi-time WWE Hardcore Champion and World Tag Team Champion with a variety of partners, but his only efforts at challenging for the WWE World Championship were extremely short and wound up in the favor of the incumbent champions.
Despite the fact Holly was never a huge success in the ring, he and Vince McMahon have held a decades-long mutual respect that has benefitted Holly in some amazing and extravagant ways. Fans and fellow wrestlers mocked Holly for his initial WWE gimmick, that of a dual-sports superstar who spent as much time racing stock cars as he did in the ring, but it paid off in a huge way. McMahon instantly took a liking to Holly and his hobby, and purchased and built him a custom stock car as a result. When WWE decided to end their weird foray into the racing world, McMahon gifted Holly the car to keep for himself. Holly never forgot the incredible act of generosity and remained a loyal employee for years.
8. Shawn Michaels And Vince Just Clicked
We’ve covered it before, but it’s such an easy fact to state, we’ll do it again: anybody who watches a single episode of Monday Night Raw from 1993 to 1997 knows that Vince McMahon is perhaps platonically, but most certainly powerfully, in love with Shawn Michaels. Vince was never as excited as when introducing the most flamboyant and charismatic superstar in WWE history, and their long standing love and respect for one another behind the scenes always played a huge role in creating that excitement. Many fans thought Michaels got better as he aged, at which point his character gradually went from McMahon’s favorite wrestler to one of his enemies, but the friendship only grew stronger as Michaels kicked McMahon’s teeth down his throat.
HBK was infamously one of the key members in a group called The Kliq, and though he shared Vince’s ear with Scott Hall and Kevin Nash, the fact Michaels was the one who stuck around when the others bolted for WCW is what made him Vince’s closest friend of the bunch as time went on. Obviously, there’s an incredible deal of mutual respect in this friendship, but especially to any fan who watched the behind the scenes video of Vince giving HBK his Hall of Fame ring in 2010 probably noticed it looked a whole lot like Vince was giving Shawn a wedding ring, and the hug they shared afterwards was long enough to make them life partners. Platonically speaking, of course.
7. The Fabulous Moolah Was Like Everyone’s Grandmother
The Fabulous Moolah has quietly become one of the most controversial names in wrestling history over the past few years as details about her training camps become more and more public, and women’s wrestling is finally free of the stranglehold she held over it for so many decades the concept nearly died in America forever. Moolah’s tamest critics call her untalented and egomaniacal, while the harsher and harder to prove stories cast her as a pimp if not an outright human trafficker. While the harsh accusations may even have some basis in reality, chances are most fans will never hear about those stories, as what we do know is the entire McMahon family loved The Fabulous Moolah like a grandmother.
Moolah left WWE in the late 80s when her in-ring talents were all but gone, but she returned in the late 90s to appear in vignettes with Stephanie McMahon in preparation of her first planned wedding with Test. Moolah was presented in grandmotherly fashion, and by all accounts, this is exactly how the McMahon’s actually treated and revered Moolah. Vince was old enough he may have treated her more like a mother, but the fact remains she was the older and gentler female presence in their lives for decades, and thus Moolah was given a great deal of reverence in return.
6. Bob Backlund Had Few Friends Outside Of Vince, Sr.
Mr. Bob Backlund has millions of fans around the world, and these days, it seems his particular brand of madness is finally getting the respect it deserves within WWE. However, for an extremely long time, Backlund felt jilted by Vince McMahon, Jr. and WWE in general for the way they treated him in the immediate wake of his first WWE World Heavyweight Championship reign. Backlund admitted this wasn’t terribly surprising to him, however, in that he made few relationships within the wrestling world during his first run outside of one extremely important connection that would dictate the rest of his career: Vince McMahon, Sr.
Though Vince, Sr. was slowing down his career and starting to hand the reigns over to his son by the end of Backlund’s time on top, it was he who decided Backlund would be a champion in the first place, and likewise Senior was the one who demanded it last so long. While critics complained Backlund was bland and uninteresting as a long serving top draw, Vince, Sr. never backed down with his favorite wrestler and good friend, and kept pushing Bob as he always promised he would. Backlund was shunted down the card immediately after Vince, Jr. took over the company, and the former champion would ultimately leave WWE for over a decade after his one ally passed away.
5. Lord Alfred Hayes Had Vince’s Letter Of Recommendation
Bob Backlund seemed to draw the short straw when Vince, Jr. took over the company from his father, as while Backlund got turfed from the spotlight almost instantly, most of Vince, Sr.’s other close friends and allies were promised cushy jobs for the rest of their lives. Chief amongst these friends and allies was Lord Alfred Hayes, best known to WWE fans as the co-host of Tuesday Night Titans and a longtime announcer for the company’s house shows and minor events. Lord Alfred was also a wrestler for several decades before joining WWE, and transitioned into a vile and hated manager for a brief period in the 80’s, but once he entered McMahon Land, he became a smiling and classy presence who the McMahons hoped would always stick around.
Unfortunately, not all friendships last forever, as McMahon and Hayes had a falling out when Vince tried to cut Alfred’s pay in 1995. Alfred retired from wrestling and left the company, never to return to the sport in any way. Vince himself was reportedly very distraught over the news, despite Alfred surpassing senior citizenship age requirements at the time. Although he was of little use in the ring or even on camera at that point, McMahon obviously realized he slighted his friend and regretted it, but at that point it was too late to fix the relationship.
4. Arnold Skaaland Was One Of Vince, Sr.’s Closest Allies
Arnold Skaaland probably isn’t a very familiar name with modern day pro wrestling fans, despite the fact he was one of the very first men inducted into the WWE Hall of Fame. Arnold Skaaland actually used to be on television all the time, as he was one of the longest tenured and most noteworthy “WWE officials” who would occasionally rush to ringside to break up a brawl between superstars, or in Skaaland’s case, be present whenever a major contract signing or in-ring presence was required by WWE management. Decades before that, Skaaland was famous as one of wrestling’s greatest managers, as he stood in the corners of both Bruno Sammartino and Bob Backlund during their legendary WWE World Championship reigns.
Skaaland was actually fairly close with both of his clients, but that didn’t compare to how close he was with the rest of the McMahon family. Starting with Vince, Sr., Arnold Skaaland was one of the most important collaborators the family would ever come across, and served as both a longtime employee and early investor in WWE. The Skaaland family’s influence would remain on WWE long after Vince, Sr. gave the company to his son, as Sr. allegedly made Jr. promise no matter what he did with the company, the Skaaland family was always taken care of.
3. R-Truth Makes Vince Laugh
The above photo was taken at the 2011 Tribute to the Troops, and has since become a somewhat legendary Internet meme. Just what could Vince McMahon and R-Truth have been discussing that made them both laugh so hard? Did Truth make the joke, or did Vince? Or was it just one of those moments between friends where it wasn’t even something they said, just something that happened? Regardless of the specifics, it achieved its level of fame primarily due to the shock value of seeing these two people, in particular, together, let alone the fact they were having such a good time.
Truth has never been a huge star in WWE or even treated like one, despite the fact he’s a former NWA World Heavyweight Champion. Truth is mostly relegated to increasingly bizarre but usually funny segments that treat him more like a literally insane joke than a potential champion contender. And nonetheless, there are stories out there claiming he’s one of Vince’s closest buddies. Neither has gone too in depth about their friendship, but Truth has said Vince’s door is pretty much always open to him, and he’s allowed a great deal of creativity over his character and particularly his self-produced entrance music.
2. Raven Was One Of Shane’s Drinking Buddies
While plenty of these stories explained how being a close friend of the boss or his family can help you succeed in WWE or elsewhere in business, there’s always that one exception that proves the rule. In this case, there’s Raven, who claims at one point he was actually Shane McMahon’s best friend. It might go even further than that, because if you listen to Raven’s stories, it seems like Shane flat out idolized him—and this was back when Raven was Johnny Polo, which means his gimmick was being the most annoying person in WWE. That obnoxious attitude is what drew Shane towards him, and in turn what Raven feels made Vince McMahon hate him.
Shane McMahon was in his early 20’s when he started hanging out with Raven, and the two had more than just a shared interest in douchey behavior. Like Raven, Shane was also a big drinker and partier at the time, and the two would travel to bars at all hours of the night, with Raven bringing Shane home to Vince blackout drunk and in terrible conditions. Raven quit WWE in the mid 90s and two gradually grew apart. Shane apparently barely talked to Raven by the time he made his return to WWE years later, and the damage was long since done to his career and standing with Vince for Shane to have fixed things, anyway.
1. Andre The Giant Was Young Stephanie’s Best Friend
Even wrestling fans who were literally born yesterday are only a short time away from learning the legend of Andre the Giant. Andre might be the most recognizable wrestler in history, thanks to his non-wrestling appearances throughout pop culture, not to mention the fact he redefined the term larger than life in a manner that no other entertainer has yet to recapture. However, it still might be a surprise to learn that his biggest fan, and in fact one of his best friends, was a pre-teenaged Stephanie McMahon.
Like many of the huge WWE stars of the 80s, Andre was close with all of the McMahon family, but it was the young Stephanie who always wanted to play and spend time with the Giant. Andre in turn liked spending time with Stephanie, and the two spent many hours together building a friendship Stephanie still fondly remembers to this day. Andre passed away in 1993 when Steph was only 16. One thing this list has proven is that the McMahons remember the past, as long as they were friends with it, so this should be a sign Andre will remain one of the most important legends in wrestling history for a long, long time to come.
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