#2 Winning the World Heavyweight Championship at Extreme Rules 2009
After losing the WWE Championship to Edge due to interference from his brother Matt Hardy at Royal Rumble 2009, The Charismatic Enigma went on a collision course with Matt, having a series of matches against his elder sibling.
After getting the better of Matt in an "I Quit Match", the Charismatic Enigma turned his attention to the World Heavyweight Champion and his arch nemesis at that time, Edge.
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After a screwy finish at Judgement Day, Edge and Hardy faced off against each other in a Ladder Match for the World Heavyweight Championship at Extreme Rules 2009. This match was filled with an array of high spot including a Twist of Fate from atop a ladder by Hardy on Edge.
The finish of the match saw Hardy trap Edge's body in the Ladder by pulling him down as he climbed up to grab the World Heavyweight Championship and become the World Champion for the very first time.
However, this victory was short-lived, as CM Punk would cash in his Money in the Bank contract on Hardy minutes later to walk out as the World Heavyweight Champion, thus starting a feud between himself and Hardy over the world title.
Hardy won back the world title from Punk at Night of Champions before dropping it back to the Straight Edge Superstar at SummerSlam before leaving the company. The sight of seeing Hardy holding the World Title while Edge is trapped in a Ladder is a visual the WWE Universe will never forget.