4 times CM Punk lost when it mattered the most

CM Punk is a rare breed. Punk has adapted and excelled as a rebellious character in the PG Era, markedly similar to Stone Cold Steve Austin at the height of the Attitude Era.

The Voice of the Voiceless is not afraid to speak up, and this anti-hero character has made him one of the most beloved figures in pro wrestling.

However, despite a long career, Punk has, thus far, not achieved the success Austin did in his prime. The primary reason has been his inability to win the most important, career-altering bouts.

Let's look at four times CM Punk lost when it mattered the most.

Disclaimer: This list is far from exhaustive and solely represents the author's views alone.

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#4. CM Punk lost to Triple H at Night of Champions 2011

The Straight Edge Superstar reached the height of his popularity in the summer of 2011, widely regarded as "The Summer of Punk."

CM Punk unleashed an iconic tirade on The McMahon Family that generated immense buzz in the entertainment industry. Soon after, news broke out that Punk's contract was nearing expiry and his final match with the company was a WWE Title bout against John Cena at Money in The Bank.

In a surprising yet memorable twist, The Voice of The Voiceless defeated Cena in his hometown and walked out with the WWE Title in front of Vince McMahon. He would later return and battle The Champ at SummerSlam 2011 to determine the Undisputed Champ, which he won.

However, his momentum quickly started to dwindle once Triple H entered the mix. HHH nearly killed all of the hype surrounding Punk's rise to the top when he defeated the rebellious superstar at Night of Champions in September.

The wrestling community unanimously claim that it was Punk's match to win. The loss halted his momentum at the wrong time, but luckily much damage was not done as The Second City Saint soon regained the WWE Championship.

Before he patched things up with Hunter, Punk boldly blamed HHH for killing "The Summer of Punk." If the former WWE Champion had won that bout, his stock would have undeniably sky-rocketed.

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#3. The Best in The World lost the 2014 Men's Royal Rumble match

CM Punk infamously walked out on the night after Royal Rumble 2014 upset with his position in WWE. The two sides' relationship deteriorated over the years, but they eventually mended fences and The Straight Edge Superstar returned at Survivor Series last year.

Assuming Punk was booked to win the 2014 Men's Royal Rumble, he could have gone on to headline WrestleMania and become WWE World Heavyweight Champion. The initial plan was for The Best in The World to have the magical 'Mania moment that Daniel Bryan had at WrestleMania 30.

However, a frustrated Punk walked out on the company and Bryan pulled off the "Miracle on Bourbon Street." If he had won the Rumble instead of Batista, he may have accomplished his lifelong goal of main eventing The Show of Shows.

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#2. CM Punk lost to The Rock at Elimination Chamber 2013

CM Punk had a generational run with the WWE Championship as he held it for more than 400 days. This should have been his ticket to stardom, but The Second City Saint got lost in the drama surrounding the John Cena-Rock saga.

Rocky returned to dethrone Punk at Royal Rumble 2013. The same night, Cena won the Rumble to book a date with his arch-nemesis at WrestleMania 29.

The Best in The World was due a rematch for the WWE Championship at Elimination Chamber. If he had won that bout, he could have interjected himself into the main event of WrestleMania 29. The company also had the opportunity to change Rock vs. Cena into a Triple Threat involving Punk too.

However, back-to-back losses to The Great One shunned Punk from the main event of The Show of Shows. Fortunately, The Voice of The Voiceless had a high-profile showdown with The Undertaker at the event.

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#1. The returning CM Punk lost the 2024 Men's Royal Rumble

Ten years after his notorious departure from WWE, The Prodigal Son returned to re-write his story and fulfill his lifelong story. The stage was set and the motive was clear: CM Punk was back to make money and close out WrestleMania.

Unfortunately, Punk met an equally, if not more, determined Cody Rhodes, who threw him over the top rope to win the 2024 Men's Royal Rumble. This was The Straight Edge Superstar's prime opportunity to grab the brass ring and finally main event WrestleMania.

The time was right, the story was there, and the crowd was firmly behind The Cult of Personality. However, WWE thought otherwise. Sadly, CM Punk suffered an injury in the same bout that removed all hopes of him competing at The Grandest Stage of Them All.