Following Punk leaving WWE in 2014, he made an appearance on then close friend Colt Cabana’s Art of Wrestling podcast in a “tell all” interview.

During which Punk made numerous claims about WWE’s negative and unsafe working environment, issues with wanting sponsors on his gear and being told no - only for Brock to return and be allowed sponsors, verbally attacking Ryback for being an unsafe worker, attacking Triple H for politicking and manipulating backstage, and eventually making a string of damning comments surrounding WWE doctor, Dr Amann and the company missing the fact Punk had a staph infection and giving him “ZPacks” to help as well as a number of other injuries he shouldn’t have worked through. This last point, was what began the legal troubles for them both.

The WWE and Dr Amann opened a Defamation lawsuit against them both. Punk and Colt would eventually win but it came at a tremendous financial cost, and this ultimately led to the breakup of their friendship.

After the podcast aired, the WWE and Dr Amann sent Colt a “demand letter”, demanding the podcasts be taken down or face legal action. Colt tabled the idea to take them down, Punk refused.

Punk said his lawyers would "handle it" in reference to the letter. Colt did nothing.

Colt was sent another letter and Punk told Colt in a text message that “I’ll make sure you’re 100% covered” for the legal fees if WWE sued, and that Colt could use Punks lawyers during the suit.

Colt left the podcast up, and the WWE and Dr Amann filed their lawsuit.

Punk and Colt signed an agreement with Punks lawyers, an agreement importantly stating Punk would be billed. In Colts eyes, this meant only Punk would pay.

When costs began to mount up, in April 2016, Punk sent Colt the following email,

"To date I have spent $513,736 dollars on this Amann lawsuit. My outstanding current bill is at least 300k. Half of all this is yours. Divide the $513,736 by 2 and that is what you owe me and what I expect you to pay me. Starting now I will no longer be paying your bills. You are on your own. Whatever my bill is currently, will be cut in half, and half will be yours. If you choose to make this ugly, that's fine too. I hope you won't, but I gave up on you doing what is right a long time ago."

Colt began looking for a new firm to represent him. Shortly later, Punk’s lawyers sent Colt the following,

“Despite your unwillingness to contribute to your legal fees, I am still prepared to represent you, and Phil is prepared to have me represent you and cover your legal fees going forward, as long as there is no conflict between you and Phil that prevents me from fairly and ethically representing you. “

Hoping there would be no conflict, Colt stayed with the firm.

Then, in March 2017, the firm, according to Colt, dropped him without explanation. Colt believed this was Punks wishes.

Punk's lawyers only stated it was due to "ethical reasons".

It’s believed, that this was caused due to Colt visiting friends at a WWE show, and Punk and team feeling this was a clear conflict of interest. Colt, reportedly refuted this and claimed he only met friends outside of the show for food, and did not attend the event.

Regardless of the reason, Colt sought new counsel with a new firm and his bills began mounting up, reaching around $200,000. Colt demanded Punk pay, in Colts eyes as per their original agreement.

Colt explained his position to his new lawyers, who in turn demands payment from Punk. Punk refused to pay Colts bills, again in Colts eyes, reneging the agreement.

Colt sued Punk for what he felt Punk had verbally, and via text, agreed upon.

Punk countersued for breach of contract, for money he felt Colt was due to pay.

In some reports, punitive damages were sought of up to $1m.

It’s reported that in total $1.2m was spent by Punk in the suit defending against WWE.

Colt's initial suit focused on text messages where Punk allegedly agreed to pay. The court ruled against him, with the court agreeing with Punk and his team that at no point did Colt provide any proof of a contract that Punk agreed to pay Colt's fees. Cabana “has failed to allege that Brooks provided an offer that was definite and certain enough to support an enforceable contract". In short, nothing Colt had shown was enough proof in the State of Illinois to show that anything Punk had done was done with deliberate intent to defraud him, or any messages between the two were a "contract" that could be enforceable by law. The case was dismissed without prejudice, meaning it afforded Colt a chance to file again with the argument reframed or with additional information brought to light.

Colt submitted a new suit some ten days later, this time focusing specifically on the fact that Punk told Colt to leave the podcasts up and if anything happened he would cover the costs, also providing the previously mentioned agreement with Punk's firm that explicitly said Punk would be "billed", and relying on the fact that Punk's lawyers emailed him using the phase "Phil is prepared to have me represent you and cover your legal fees going forward".

Punk's countersuit focused on the fact that, whilst the agreement with Punk's lawyers said Punk would be billed. The two parties were "silent with respect to how Brooks and Colton could, would or should allocate the Loeb Firm’s fees and expenses among themselves or whether how and when Colton should reimburse Brooks".

Punk's lawyers also pointed to their original agreement that said, "although we are not aware of any conflict that presently exists between the two of you, the potential for such a conflict exists. If an actual conflict were to arise in the future, we may not be able to represent Scott [Colton] in the Amann Lawsuit"

With regards to Colt being able to afford the suit. Punks lawsuit noted that Colt made more than enough money from the podcast itself through advertisements and sponsors, youtube ad revenue and merch sales from the show. Noting that within five days of the CM Punk episode, that episode was streamed or downloaded 1.5 million times, the largest audience ever for that podcast series. Within a week, that number was up to three million. Punk's defence was that Colt would have made more than enough money from the show itself to offer to pay his fair share.

Punk's lawsuit also alleged that when Colt received the Demand Letter from WWE/Amann, Punk fully believed that Colt "had a commercial and financial incentive to leave episode 226 available for public consumption and not comply with the Demand Letter." - Essentially that not only was Colt leaving it because Punk suggested to, but also because Colt knew he would make a lot of money from the show if he left it online.

The lawsuits between the two were dismissed, coincidentally, one day before Fox signed an agreement with CM Punk to appear on their show WWE Backstage (to be clear, this is not a WWE contract). Meaning no dirty laundry or nasty legal cases would be going on whilst Punk was employed and back in the public eye on a WWE related broadcast.

Colt, to my knowledge, has never publicly commented on the suits, but the above has been covered in various reputable sources including the Chicago Sun-Times and Forbes.

Punk has occasionally publicly commented on this. On Twitter and now more infamously during the media scrum.

Punk has stated he offered to settle, to talk, to mediate and Colt refused.

Likely, Colt believed he was not due to pay anything as, in his mind, Punk originally promised he wouldn’t.

On Punk’s side, the costs spiralled, and he stuck by, what was in his view, was only fair, Colt pay his part of the costs incurred.

With the friendship well and truly done, Punk obviously later joined AEW where Colt was signed. When Colt stopped appearing regularly on tv and reports began circulating that he’d been moved to ROH… the rumours began that Punk was behind this, or at the very least rumours were that Tony moved Colt there to avoid any possible conflict… which Punk vehemently denied during the scrum. For that, and all of Punks other comments you can watch the scrum or read recent posts.

Edit: I’ve not covered the scrum itself or accusations by made by punk in the scrum, this was specially about what got us into the lawsuits and why the fell out.

Edit 2: couple of people have said they’ve seen some inaccuracies but haven’t mentioned what they are. More than happy to update this to make it more accurate if you guys actually say what they are and cite a source 🙂👍🏻

Edit 3: clarified that Punks contract was with Fox not WWE and that it’s widely believed the reason Colt was dropped from the firm was that Colt visited a WWE show, a point which Colt has denied saying he went for dinner with friends after a show.

Edit 4: added a minor summary of AEW rumours around Colt/Punk tv time and ROH.

Edit 5: added sources for the suits between the two and some additional info on the particular cases.

Sources:

https://www.forbes.com/sites/davidbixenspan/2019/09/29/cm-punk--colt-cabana-settle-lawsuits-over-legal-fees-from-wwe-doctor-case/

https://chicago.suntimes.com/news/colt-cabana-cm-punk-contract-legal-fees-lawsuit/

https://www.pwinsider.com/article/127507/cm-punk-files-lawsuit-against-colt-cabana-in-response-to-cabanas-existing-lawsuit.html?p=1

https://www.pwinsider.com/article.php?id=122387&p=1