If there's one thing we know about Vince McMahon, it's that he demands loyalty from his wrestlers.
Pro wrestlers might have a short career in the grand scheme of things, meaning the very best usually stick around in WWE.
If you show the boss loyalty, he'll show it back to you.
Just look at his relationship with The Undertaker.
Those two would go to war for each other. In fact, we can almost picture them in the trenches together, fighting side by side.
But 'Taker isn't the only wrestler who could be considered loyal to WWE and there are plenty of other long-serving performers in the company.
Let's take a look at the 10 stars who have been on McMahon's roster for the longest.
10. Natalya | 13 years
Natalya is the second longest-serving female star currently under contract in WWE.
As the daughter of Jim Neidhart, wrestling runs in the family and for that reason, it's hardly a surprise she's been with WWE for so long.
9. Kofi Kingston | 14 years
Kingston signed a developmental contract with WWE in September 2006 at the age of just 24 - and he hasn't looked back since.
Beloved by fans as a member of the popular New Day tag team, he even had a famous run with the WWE Championship in 2019. With that win, he became a grand slam champion.
8. R-Truth | 16 years (two runs)
One of WWE's most loved stars, R-Truth isn't exactly a main-event player, but he's comedy gold every time he's on screen.
The current 24/7 Champion has had two runs with the company, the first coming between 1998 and 2002 as K-Kwik before returning in 2008 with a new ring name.
In total, R-Truth's two WWE runs combine for 16 years.
7. The Miz | 16 years
The most 'must-see' superstar in WWE is also one of the longest-serving. The Miz debuted in 2004 as part of the Tough Enough competition show.
Despite losing his match, he was offered a developmental contract and hasn't looked back since.
Miz is a former WWE Champion, who has also won the Intercontinental Championship eight times, the US Championship twice and he's also an eight-time tag-team champion.
6. Dolph Ziggler | 16 years
After signing his WWE contract in 2004, Ziggler debuted as a member of The Spirit Squad. That gimmick soon ran its course and 'Nicky' as he was known back then, returned to developmental.
Less than 12 months later he made his comeback on RAW as Dolph Ziggler and a star was born.
He's had multiple runs with the World Heavyweight Championship, US title, Intercontinental Championship and tag team belts, becoming one of the few Triple Crown Champions in WWE.
5. Randy Orton | 19 years
It's hard to believe he's been hearing voices inside his head for almost two decades now. Randy Orton was always destined to be a top star in this business though.
From 'Legend Killer' to 'The Viper', he's dominated for 19 years and almost everybody on the roster has felt the three most dangerous letters in WWE... RKO.
4. John Cena | 20 years
Cena might not be a staple of WWE anymore, but he's still signed on to a part-time deal, so technically... 'his time is still now'?
On a serious note, he's achieved so much in WWE and will always be renowned as one of McMahon's most loyal wrestlers.
He used to wear 'Hustle, Loyalty, Respect' gear as well to really hammer home that point. Don't bet against him beating Ric Flair's world championship record one day to reward that loyalty.
3. Big Show | 21 years
The World's Largest Athlete is also WWE's second longest-serving performer, having signed his first deal way back in 1999.
Since then, he's reached the top of the mountain and worked as an established main event star for many years.
Big Show's time in the ring looks all but done, but he's still under contract with the company and has recently appeared at WrestleMania, Clash of Champions and on Monday Night RAW.
2. Triple H | 25 years
Triple H is the man that many people expect to take over from McMahon when he's gone and to be honest, there's no one better.
'The Game' simply lives and breathes this business and has already shown he can handle the pressure by turning NXT into an incredible product.
Aside from running things behind-the-scenes, We still think he's got a least one more WrestleMania match in him though...
1. The Undertaker | 30 years
No one else was going to top the list. This spot belongs to one man only - The Undertaker.
After a stunning in-ring career that lasted for three decades, The Deadman has confirmed his match against AJ Styles at WrestleMania 36 was his last.
But, never say never in WWE. If Vince ever needs him, he'll be back. Especially after signing a new 15-year contract back in May. 'One more match... one more match!'
So there we have it. 10 of WWE's most loyal superstars. From The Undertaker to Natalya, Vince McMahon has a strong crop of talent that will always have his back.
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