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Although Helmsley was highly promoted in the first few months after his debut, his career stalled during 1996, starting off with a feud with Duke "The Dumpster" Droese following a loss during the Free for All at 1996 Royal Rumble.

When he attempted to perform the Pedigree, Garner mistook the maneuver for a double underhook suplex and tried to jump up with the move, causing him to land squarely on top of his head and suffer neck damage.

During this time, he adopted an entrance gimmick of asking the crowd "Are you ready? ", followed by a parody of rival promotion WCW's ring announcer Michael Buffer's famous catch-phrase, "Let's get ready to rumble", substituting the word "rumble" with the DX slogan, "suck it".

Also during this time, Triple H began a feud with the leader of the Nation of Domination and rising WWF villain, The Rock.

In July 1992, he defeated Mad Dog Richard to win the IWF Heavyweight Championship.