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It’s often said that loyalty goes a long way in life, and this is especially true in WWE. Vince McMahon, for all his negative personality quirks, is a man that appreciated loyalty above all else and awards those that stay with him.
Loyalty is paramount to WWE, which is why many employees that work for him for lengthy periods get ‘rewarded’ with certain perks and gifts. For wrestlers, such loyalty usually comes in the form of a world title run or some other major perk in their contracts or payments.
For non-wrestling employees, loyalty usually turns into some kind of special recognition backstage, as well as a promise of ‘being taken care of’ especially after said person retires. Both Vince McMahon and his father have been known to ‘take care’ of certain employees after they retired or left, as a sort of special thanks for so many years of sacrifice.
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This level of respect usually extends to those employees that have worked for WWE for the longest periods, and the ten people mentioned here have all worked for WWE longer than anyone else.
10: Big Show
Paul ‘Big Show’ Wight was, until February 2018, one of WWE’s longest-tenured wrestlers, having signed with the company all the way back in early 1999. At the time, he signed a massive 10-year contract, and was catapulted to the main-event of the company shortly after said contract was signed.
In the almost two decades that followed, Big Show has done almost everything imaginable in WWE. He has worked lower-card comedy matches and main-events. He has been a singles champion and a reliable tag team for many a smaller wrestler. He has been both an unstoppable evil giant and also a champion for good. He was even been made to cry on TV at one point, though that might not necessarily be one of his career high points.
Given all of his accolades in WWE, one cannot deny that loyalty and commitment to your employer can yield many positive outcomes for your career.
9: Mark Henry
Mark Henry, also known as the ‘World’s Strongest Man’ is also one of WWE’s longest-tenured employees. After winning numerous strongman and powerlifting accolades throughout the 1990s, Henry joined WWE in 1996, and has been with the company ever since.
He signed multiple lengthy contracts throughout his tenure, and has been a regular fixture on WWE programming ever since. Henry spent more or less twenty years on WWE programming, engaging in feuds all over the card. In some years, he was a top threat for world titles and a true danger to the entire roster, while in other years he was a comedy wrestler with sometimes less-than-desirable character quirks.
However, his loyalty to WWE led to many important moments for him, including a run as World Heavyweight Champion back in 2011. Even after some people tried to break him (especially through some of his early gimmicks, which were meant to embarrass him), Henry stayed loyal to WWE, which is admirable if anything.
8: Michael Cole
Michael Cole is arguably the longest-tenured commentator in WWE history, having been an on-screen commentator for almost twenty years. He first started working for WWE in about 1997, but didn’t become a regular commentator until about 1999, as he replaced Jim Ross quite a bit during that period because J.R. was suffering from Bell’s palsy complications at the time.
As a commentator, Cole has been the subject of much criticism. Unlike Jim Ross, who would often show considerable enthusiasm in his commentary and sell the emotions he was feeling as a ringside commentator, Cole’s commentary has often felt too ‘sterile’ and professional, and thus lacking in the emotional emphasis of his predecessor.
This has worsened to an extent in recent years, as poor Cole has found himself in a position where he has to regurgitate what’s fed to him by Vince McMahon and company, even if Cole himself disapproves of it.
Yet given that fact, one should commend Cole for showing such immense patience and maintaining a sense of professionalism, especially since he might have to deal with actual shouting in his head-set on a weekly basis.
7: Kane
Glenn ‘Kane’ Jacobs is the perfect definition of loyalty and devotion in WWE. He has been employed with the company since 1995 and has stayed with the company ever since. Although he does have his own side business and is engaging in political endeavors outside of the wrestling business, Kane still seems to come and go as he pleases in Vince’s company.
This is because Kane is arguably the most loyal and cooperative people to ever set in foot in WWE. He has long towed the company line in all of his storylines, and has done whatever the creative forces have asked of him, without question. Even in WWE, wrestlers are known to argue creative decisions or use their own political clout to change decisions if they can.
But not Kane; he has done whatever was asked of him, no matter what the consequences – positive or negative – might be. So while many external observers have long lambasted Kane and criticized his various rivalries and creative segments, the man himself has gone with whatever was given to him.
Given that loyalty, it wouldn’t be surprising if WWE had a wall showing various ‘Employee of the month’ awards, with the majority of those awards having Kane’s (masked) face on them.
6: Triple H
Triple H’s name has become synonymous with WWE over the past number of years. He has been one of the most influential forces in WWE history, playing a critical role in many key moments. He was a member of the Kliq and was the one that came up with the idea of the Montreal Screwjob.
He played a major role in D-Generation X and feuded extensively with the Attitude Era’s top stars. Finally, he married Stephanie McMahon and became a critical member of WWE’s decision-making process, while also running the NXT brand as his own creation. Triple H has been employed by WWE for around 23 years, and has become one of its most critical individuals, especially in terms of creating the stars of tomorrow.
Given his passion for the wrestling industry and his blood ties to the McMahon family, it isn’t likely that his involvement and employment with WWE are going to diminish in any way in the foreseeable future.
5: The Undertaker
In terms of wrestling talent, no wrestler in WWE can match The Undertaker in terms of tenure, loyalty and respect. He has been employed with WWE since late 1990, and has remained loyal to Vince McMahon ever since.
Even when prospects looked to be at their gloomiest, ‘Taker never made the jump to other promotions or betrayed Vince in any way. This exemplary demonstration of loyalty has made him into a bona fide legend in the company, and acts as a standard for others in the company.
In fact, when Undertaker was taken to a hospital after his match with Brock Lesnar at WrestleMania XXX, Vince McMahon went with him, leaving the WrestleMania control room for the first time in his life.
Only his most loyal employee would command such respect from his boss, and that’s exactly what the Undertaker does: he is universally respected for his loyalty and his willingness to sacrifice himself for the good of WWE.
4: Mike Chioda
Mike Chioda is WWE’s longest-tenured referee, having made his first appearance for the company in 1989 and became a regular referee for the company around 1992. Given his long tenure with the company, Chioda has earned the privilege of officiating many important matches in WWE history.
These include: ‘Stone Cold’ Steve Austin vs. Shawn Michaels at WrestleMania XIV, the Big Show-Brock Lesnar ring-breaking superplex match, the main event of WrestleMania 23 between John Cena and Shawn Michaels, John Cena vs. The Rock at WrestleMania XXVII, Roman Reigns vs. Brock Lesnar at WrestleMania 31, and Roman Reigns vs. Seth Rollins at Money in the Bank 2016 (and also Dean Ambrose’s subsequent cash-in).
Simply put, this man has been involved in many historical moments in WWE history, and that’s thanks to both his skill as a referee and for his loyalty to the company.
3: Kevin Dunn
There is very little known about Kevin Dunn; in fact, if you were to visit WWE’s ‘Corporate’ page, his description and title are there, but no photo is available. He has also rarely been mentioned on-screen by anyone in WWE, except on a few rare occasions, and even those were ‘blink-and-you’ll-miss-it’ moments.
What little info there is on this man tends to come from secondhand sources, and unfortunately, most of the opinions on this match tend to be negative. According to the most reputable sources, his father worked for Vince McMahon Sr., and he once saved some crucial WWWF tapes from a burning truck. To thank him, Kevin was given a job in WWE for life, and has been employed with WWE since 1984.
His main function has been that of Executive Vice President of Television Production, meaning that aside from Vince McMahon, he’d the head honcho for production of televised events.
However, much of the criticism towards him tends to be centered on the notion that he dislikes everything related to wrestling itself, and prefers things that are more geared towards ‘entertainment’ and ‘reality TV’.
In other words, if you’re one of those people that bemoans WWE’s production of such things as Diva Searches, Tough Enough, and terrible TV-soap-opera-style stories, you can thank this man, as those things are the kinds of ideas he tends to emphasize.
2: Patt Patterson
Patt Patterson has long been considered Vince McMahon’s ‘ right-hand man’ in terms of ensuring that WWE’s machine run like clockwork, while also playing an integral role in WWE’s first major expansion into the international market.
He has filled many roles over the years in WWE, including that of a backstage agent, a road agent, a creative figure, and as an on-screen character as well. Patterson was the first WWF/E Intercontinental Champion and was also the creative genius behind the Royal Rumble.
Patterson started working for WWE in the late 1970s, and worked with the company fulltime until about 2004 (save for a short period in 1992, during which he left WWE after sexual harassment allegations).
Because of his numerous accolades and how much he has influenced WWE in general over the years, he is one of the few people in WWE worthy of being considered company ‘royalty’.
1: Howard Finkel
Howard Finkel has been employed in the company now known as WWE longer than any other employee. He first started working for Vince McMahon Sr. in 1975 and for WWE in 1977. He has been with the company ever since, working primarily as an announcer for many of WWE’s different wrestling programs.
Finkel has a unique announcing style whereby he’d always but extra emphasis on the word ‘new’ when announcing a title change. This, in turn, made audiences react even louder whenever such decisions happened, making Finkel a great announcer in WWE.
Finkel hasn’t appeared that much in recent years, being more of a part-timer that does special announcements on important showed. However, given that he’s still employed by WWE, it’s clear that he’s one of many people that Vince Sr. asked his son to take care of after he passed ownership of his company onto his son.
