#1. Triple H - been with WWE for 25 years
Triple H is one of the most powerful men in wrestling at present and has proved his worth as one of the best minds in the business during his time as "The godfather of NXT."
That being said, Triple H joined WWE as an active talent back in 1995 after a brief stint in WCW. At the time, Triple H was known as Hunter Hearst Helmsley and would later find success as a member of D-Generation X.
After DX went their separate ways, The Game stepped into a feud with The McMahon Family, which is when he began a relationship with Mr. McMahon's daughter Stephanie, both on and off-screen.
The couple officially married in 2003 and have since welcomed three daughters. Triple H has continued to work as an active talent for WWE over the past two decades and is now a 14-time World Champion.
Despite moving into a backstage role and picking up the responsibility of NXT, Triple H still continues to wrestle sporadic matches for WWE when needed with his last match coming back at Super ShowDown in 2019 where he lost to Randy Orton.
Triple H is yet to retire from WWE and celebrated his 25th anniversary in WWE back in April.