Money in the Bank and World Heavyweight Champion (2008–2009)

CM Punk in April 2008 with his first of two Money in the Bank briefcases.
At WrestleMania XXIV, Punk won the Money in the Bank ladder match, after defeating Chris Jericho, Montel Vontavious Porter, Shelton Benjamin, John Morrison, Mr. Kennedy and Carlito.[75]
On the June 23, 2008 Raw, CM Punk was drafted to the Raw brand during the 2008 WWE Draft.[76] His first night on Raw came the following week, and he made an immediate impact. After Batista beat down World Heavyweight Champion Edge and left him lying in the ring, Punk and referee Mike Chioda ran to the ring with Punk carrying his Money in the Bank contract. Moments later, as Edge was struggling to get up, Punk hit him with the Go to Sleep and pinned him to win the World Heavyweight Championship (and later, the Slammy Award for the "Oh my God" Moment of the Year.[77]). Later that night, Punk made his first defense of the title against JBL, who had challenged him shortly after his win.[78] Punk continued to hold and defend the title until Unforgiven on September 7, 2008. Before the Championship Scramble match, Punk was attacked by an early version of The Legacy (Randy Orton, Cody Rhodes and Ted DiBiase with Manu). Orton finished the assault by punting Punk in the head.[79] Punk could not participate in the match due to the attack and so forfeited the title. He was replaced by Chris Jericho, who won the match and the title.[80] He received a rematch eight days later on the September 15 Raw, where he failed to regain the title in a steel cage match against Jericho.[81]
CM Punk as World Heavyweight Champion during his first reign at SummerSlam.
On the October 27, 2008 Raw, Punk and Kofi Kingston defeated Cody Rhodes and Ted DiBiase to win the World Tag Team Championship.[82] The duo were members of Team Batista at Survivor Series, where their team lost to Team Orton.[83] Punk then entered in a number one contender Intercontinental Championship Tournament. He defeated Snitsky and John Morrison in the first two rounds.[84] Punk and Kingston lost the World Tag Team Championship to John Morrison and The Miz at a live event on December 13, 2008.[85] The next day Punk defeated Rey Mysterio at Armageddon to win the tournament.[84] On the January 5 Raw, Punk received his title match against William Regal, which ended in a disqualification, when Regal grabbed the referee's jersey.[86] Due to this, Stephanie McMahon awarded Punk a rematch the following week, but this time it was himself that was disqualified.[87] McMahon awarded him another rematch, this time a No Disqualification match on January 19 Raw, Punk won the match and the title.[88] With this win, he became the nineteenth Triple Crown Champion. Also, the victory made him the man to accomplish the Triple Crown in the fastest amount of time, shattering Kevin Nash's old record.[89] Punk lost the title on the March 9 Raw to John "Bradshaw" Layfield.[90] At WrestleMania XXV, Punk won the Money in the Bank ladder match and became the first person to win the match twice.[91]
On April 13, 2009 during the 2009 WWE Draft, Punk was drafted from Raw to SmackDown.[92] In the period after the draft, Punk feuded with Umaga over Umaga's repeated surprise attacks while Punk was attempting to cash in his Money in the Bank Contract. This ultimately resulted in a Samoan strap match at Extreme Rules, which was won by Punk.[93]
At the end of the pay-per-view, Punk cashed in his Money in the Bank contract to defeat Jeff Hardy for the World Heavyweight Championship.[94] Punk retained his title in a Triple Threat match against both Edge and Hardy eight days later on the June 15 Raw.[95] At The Bash in Sacramento, California, Punk lost to Hardy by disqualification after kicking the referee after being afflicted with a storyline eye injury, claiming he could not see the referee, but because titles do not change hands on a disqualification, Punk retained the championship. Hardy called Punk into question about his eye injury, believing he had been feigning it, leading Punk to turn heel, claiming to be the moral superior of those who support Hardy due to his drug-free lifestyle.[96] At Night of Champions, Punk lost the championship to Hardy.[97] Their feud continued through SummerSlam, where Punk regained the title in a Tables, Ladders, and Chairs match; afterward, Punk was attacked by The Undertaker.[98] On the August 28 Friday Night SmackDown, Punk concluded his program with Hardy and achieved his booked goal of excising him from WWE, defeating Hardy in a steel cage match wherein the loser agreed to leave the company.[99] This earned Punk a second Slammy that December, for 2009's "Shocker of the Year".[100]
At Breaking Point Punk defeated The Undertaker in a submission match to retain the World Heavyweight Championship. Undertaker originally won the match with his Hell's Gate submission hold. SmackDown general manager Theodore Long restarted the match after stating that the ban that former general manager Vickie Guerrero had placed on the move was still in effect. Punk won the match with his Anaconda Vise when referee Scott Armstrong called for the bell despite Undertaker never submitting (reminiscent to the Montreal Screwjob, which took place in the same venue in 1997).[101] The feud between the two continued and at the Hell in a Cell PPV, Punk lost the World Heavyweight Championship to The Undertaker in a Hell in a Cell match.[102] He lost two subsequent rematches against The Undertaker on Smackdown and in a Fatal Four Way match at Bragging Rights also involving Batista and Rey Mysterio.[103][104]