Hunter
Hearst Helmsley's history in pro-wrestling starts much like his bodyguard,
Chyna's. They both attended 'Killer' Kowalski's wrestling school in Boston.
Kowalski saw Helmsley's talent and so set him up in the IWF, and indie
wrestling federation that worked closely with Kowalski's school, much like
WCW and the Power Plant today. His first wrestling name was Terra Ryzing.
He went on to become the IWF Champion some months later.
Terra Ryzing joined the WCW for a short period of time, where he won his first match against the Road Dog, Jesse James (then known as Brian Armstrong). He won a few more matches, only to lose a TV title match to Larry Zbysko in 1994. Ryzing disappeared and Helmsley reappeared in the WCW as Jean-Paul Levesque (Helmsley's real name), a French-Canadian aristocrat with a gimmick much like Lord Steven Regal's.
Levesque was short lived as he moved to the WWF in 1995
and became Triple H, with much the same gimmick he had before the move.
It was here in the WWF that Helmsley met the likes of Shawn Michaels, Scott
Hall, Kevin Nash and Sean Waltman, all 5 of which would form the 'Kliq',
the largest group of real-life friends in wrestling today.
A couple of years later, after a somewhat successful feud
with Duke 'The Dumpster' Droese, a 98-second loss to the Ultimate Warrior,
and another feud with Marvelous Marc Mero (over Sable), Helmsley was slated
to wrestle Razor Ramon (Scott Hall) one night at the Madison Square Gardens,
while Shawn Michaels was supposed to face Diesel (Kevin Nash). These long
time friends wrestled, and Hunter and Shawn won, but afterwards (as it
was to be Hall and Nash's last matches in the WWF), they all hugged in
farewell. This was 
a
direct violation of the rule of keeping the inner workings of wrestling
a secret. Vince MacMahon was enraged, and Helmsley became the fall-guy,
because Shawn was the champ.
After his feud with Marc Mero and short stint with Mr.
Perfect Curt Hennig as his manager, Helmsley showed a certain amount of
interest in Marlena, Goldust's valet. The two finally faced off at the
Royal Rumble 1997, where Helmsley won with the help of his 'butler', Curtis
Hughes. Hughes had some health problems and was forced to leave the WWF.
Helmsley was left alone once more, but this time, aid came to him in the
form of Chyna, who manhandled Marlena and helped Hunter in his feud with
Goldust. With the help of Chyna, HHH went on to become the King of the
Ring in 1997.
Soon after, Shawn Michaels, Helmsley and Chyna went on
to form Degeneration X, a new group who were touted to break every rule
of the WWF. Degeneration X has become one of the most exciting stables
in the WWF today. With the addition of Sean 'X-Pac' Waltman and Jesse James
and Billy Gunn, the New Age Outlaws, DX gets larger all the time.