CM Punk became the first (and to date, only) superstar to win two Money in the Bank ladder matches in 2009, when he defeated seven other men at WrestleMania XXV to claim the briefcase for the World Heavyweight Championship. Two months later, World Heavyweight Champ Edge was defending his title against daredevil Jeff Hardy at Extreme Rules in a ladder match that harkened back to their tag team title TLC matches. Hardy emerged victorious, only for Punks music to hit. Two Go to Sleeps later and Punk had captured his first WHC. That cash-in served a huge purpose in the career of Punk, turning him heel for the first time in his WWE career. It also pitted him against Hardy, which allowed Punks Straight Edge Superstar persona to emerge as he battled a wrestler with a checkered past. Punks ensuing feud with Hardy elevated Punk and set the stage for the Straight Edge Society. Months after that group disbanded, he took over the New Nexus, which ended when he dropped a pipebomb.
Scott is a former journalist and longtime wrestling fan who was smart enough to abandon WCW during the Monday Night Wars the same time as the Radicalz. He fondly remembers watching WrestleMania III, IV, V and VI and Saturday Night's Main Event, came back to wrestling during the Attitude Era, and has been a consumer of sports entertainment since then. He's written for WhatCulture for more than a decade, establishing the Ups and Downs articles for WWE Raw and WWE PPVs/PLEs and composing pieces on a variety of topics.