The Funniest Lawsuit In The Universe

The Funniest Lawsuit In The Universe

Unraveling the $380M feud between Maddox and Dick Masterson

Image for postAsterios as The Enigma, Madcucks donning a stack of paper crowns, and Dick Masterson in his mansplainer outfit (drawing by KenDollInHide)

Sometimes a lawsuit comes along that makes Costanza v. Seinfeld look like it stood on solid ground ? a legal action so ridiculous as to defy all belief. Let me tell you about the lolsuit (full docket at, a little gem I stumbled upon in the wild as a fan of many of the defendants involved.

The lolsuit is a hilarious, absurd, and thoroughly entertaining $380M action filed by internet satirist Maddox (of The Alphabet of Manliness and The Best Page in The Universe) and his girlfriend against Maddox?s former business partner and fellow satirist Dick Masterson, many of his friends and comedy partners, and the companies that employ or fund them.

Out of respect of their privacy, whenever applicable, all persons involved are referred to by their online handles rather than their real names.

A Quick Background

Maddox is one of the fathers of internet satire. Adopting the persona of a manly and narcissistic pirate, he starts The Best Page In The Universe in 1996, where he rants about the minutia of pop culture while satirizing feminism and championing manliness. His internet popularity grows quickly and his first book, The Alphabet Of Manliness, becomes a New York Times Bestseller.

Dick Masterson is a satirist with an over-the-top chauvinistic persona who rose to fame through the website Men Are Better Than Women, the eponymous book, and a five-day stint on Dr. Phil in which he appeared in character donning aviators, a shaved head and 70s porn stache.

In May 2014, Dick and Maddox start co-hosting a weekly comedy podcast, The Biggest Problem In The Universe. It?s the Seinfeld of podcasts, replete with funny rants, absurdist arguments and first-rate comedy bits.

A clip from The Biggest Problem In The Universe, Episode 69

The great chemistry between the co-hosts starts waning after Dick sleeps with an ex-girlfriend of Maddox?s (of three years prior, and despite Maddox being already involved with a live-in girlfriend).

Unfortunately, this point in time also marks the start of Maddox?s estrangement from his own fans ? and, some would say, reality itself. Maddox?s topics on the comedy show increasingly become more political, taking a hard left, and he becomes more and more incensed by comments from listeners who rebut his points or criticize him in any way. In a dubious move, Maddox ? who, as a satirist, built his reputation on being an attentive observant of pop culture ? manages to publish a video in which he completely misunderstands the meaning of the internet insult ?cuck? and staunchly proclaims that ?There?s nothing inherently wrong with being a cuckold!,? which sparks an endless barrage of mockery from his own fans.

Maddox ends the podcast a few months later, and both co-hosts start their own shows. The reason for the split is unknown to the audience, but Dick seems to suggest it was amicable, while Maddox does not publicly mention the matter at all. Dick starts taking lighthearted jabs at Maddox for, among other things, taking the RSS feed of the old show and redirecting it to his own.

But Maddox still doesn?t seem to have forgiven his friend?s escapade with his ex-girlfriend. About four months into the new shows, Maddox focus-tests and then releases a ?hit job? YouTube video based on comically poor evidence and out-of-context audio cut from the old show in which he accuses Dick of lying (launching the #DickLies hashtag), embezzling funds from the old podcast, being a ?rape apologist,? and maintaining a ?rape list? through his show. Although the accusations are easily disproved, because of Maddox?s clout, Dick loses several contacts and business opportunities in the comedy scene.

After responding to the accusations point by point, Dick starts taking more jabs at Maddox. Madcucks, a Maddox parody, becomes a frequent guest on Dick?s show (the ?cuck? reference coming from Maddox?s earlier video).

Image for postMaddox (left, public domain image) and Madcucks (right, YouTube screenshot)

In January 2017, Maddox files a trademark for the name of the old show, listing himself as the sole owner. Dick successfully opposes the trademark and the registration is refused in April 2018.

Metal Jess, Maddox?s live-in girlfriend, publishes a private message from Asterios Kokkinos, an outspokenly liberal comedian and recurring guest on The Biggest Problem, in which Asterios is consoling her for the stress and humiliation Maddox has supposedly incurred through Dick?s jokes and the Madcucks parody. The apparent reason for Metal Jess publishing the private message is to accuse Asterios ? a long-time friend of both Dick and Maddox ? of trying to play both sides in the Dick/Maddox rivalry.

Enraged by what happened, and as a way of response, Asterios cuts ties with Maddox. In 24 hours, he puts together Cuckmas Carols: Bald Headed Lies, a comedy album poking fun at Maddox, with such classic hits as Little Cuckold Boy and Twelve Days of Cuckmas. The album is an overnight success and becomes a Billboard-charted album (#11 in all of Denmark on iTunes).

A mysterious woman calls the school where ?80s Girl? ? the Helen of Troy who was a former girlfriend of Maddox, slept with Dick, and is now Dick?s girlfriend ? works as a teacher. The caller levies some baseless accusations, stating among other things that ?she shouldn’t be around children.? The woman is persuaded to leave her name and phone number with the school: as it turns out, the mysterious caller is Metal Jess herself. Shortly after, 80s Girl is granted a restraining order protecting her from Maddox?s live-in girlfriend.

All of this drama culminates in November 2017, when Maddox and Metal Jess decide to file a surprise 380 million dollar lawsuit against Dick, Asterios, Madcucks, (the platform all three use to raise funds for their content), a customer service representative at Patreon (sued as an individual rather than in his capacity as an employee), Weber Shandwick (Asterios?s employer) and its lead counsel (also sued in his individual capacity), a company co-owned by Dick, and the other co-owners of that same company.

The Lolsuit

The original complaint is a ? shall we say one of a kind?53-page document alleging a dog?s breakfast of causes of action against the many defendants. Multiple lawyers have gone through the documents and pointed out its many weaknesses, inconsistencies, hilarities, and self-incriminating statements (see YouTuber Law for short-form videos, Nick Rekieta for a line-by-line analysis).

The document is so poorly drafted ? with criminal overuse of apostrophes, horrible punctuation, stretched-out Twitter screenshots as inline exhibits, an either willfully obtuse or embarrassingly poor reading of the law, conclusory statements with no supporting evidence, Metal Jess inexplicably being initially listed anonymously as ?Jane Doe,? and little jabs such as ?How is that for irony?? and ??or so Plaintiff had thought? ? that nearly everyone in the Dick Show community initially assumes Maddox has drafted the document himself and had a lawyer sign it and submit it to the courts on his behalf.

Image for postFrom page 23 of the lolsuit

Not that the complaint was submitted to the right courts, either. Despite most defendants being California residents (including Dick and Maddox, who live just a few miles apart), the suit is filed in New York, a venue appropriate only for, at best, two of the many defendants ? Asterios and his employer. The main two reasons for Maddox to sue in New York may be on one hand the targeting of Asterios, since (as we?ll see later on) Maddox is clearly trying to get him fired from his regular job; and, on the other hand, the plaintiffs are trying to avoid California?s anti-SLAPP laws that would make it easy for the defendants to countersue and recover attorney?s fees.

There?s no better way to expose the hilarity of a frivolous $380M complaint than to go through the causes of action and the reliefs requested one by one. However, because there are 16 causes of action, some will be grouped together and their damages added up for the sake of brevity.

Asterios, Madcucks, Dick, his company and its co-owners are being sued for:

Invasion of privacy

Despite its name, invasion of privacy has little to do with privacy and instead deals with the unlawful use of a person?s likeness for purposes of advertising.

This doesn?t stop Maddox and Jess from suing Asterios under this claim for mentioning Maddox in the Cuckmas Carols album and allegedly revealing Metal Jess?s phone number (the number was 867?5309, a pop reference).

Image for postThe phone number given out by Santa Cuck (Source)

Dick is being sued under this claim for featuring a drawn caricature of Maddox as the devil for one of his shows (which took place outside New York), and for merely commenting on a picture of Metal Jess on Twitter.

Dick and Asterios together are also alleged to have created the Madcucks parody ? more on that later ? and for targeting Facebook advertisements to Maddox?s fans (which is perfectly legal).

Madcucks is sued for allegedly profiting from his parody of Maddox (which is nonsensical, since parody is a highly protected form of free speech).

Finally, Dick?s company and its co-owners are said to have stored defamatory information on their servers (no proof of this whatsoever is provided).

Relief requested: 20 million dollars; an (unconstitutional) injunction not to use Maddox or Mental Jess?s names or likenesses on any platform, in anycapacity, in perpetuity (from here on, ?the injunction?); taking any ?offensive content? offline; and the sequestration of the servers of Dick?s company.

Image for postThe Most Unconstitutional Injunction in the Universe (page 32 of the lolsuit)


Defamation in the legal sense deals with statements of fact that are knowingly false and uttered with the intent to damage another. Opinions don?t apply, and defamation toward public figures (which Maddox makes himself out to be by saying he?s a NYT bestselling author) is harder to prove.

Maddox tries to get around the high threshold for public figures by claiming per se defamation ? alleging that Dick & co. uttered statements that were so vicious that damages should be presumed and don?t need to be proven.

So, what did the defendants say that was so abhorrent? They made fun of Maddox and Metal Jess, called Maddox a cuck (even though, you?ll remember, Maddox said there was nothing inherently wrong with that), made ?rape and death threats? (the proof for this consists of screenshotted comments from fans, not any of the defendants, that are themselves not threats and not actionable), and encouraging fans to ?stalk and harass the plaintiffs? (no proof of this whatsoever is provided).

Relief requested: 20 million dollars; another 20 million in exemplary and punitive damages; a complete retraction of any disparaging comment; and a?comprehensive, public apology toward Plaintiffs? (even though it would beunconstitutional for a court to compel speech in this way).

Image for postThe author of ?The Alphabet of Manliness? requesting $40M in damages and a public apology for getting called a ?cuck? on the internet (page 34 of the lolsuit)

Misappropriation, unfair and deceptive trade practices, and unfaircompetition

The facts alleged here are similar to those in the invasion of privacy claim, including actions such as including a Maddox caricature in a ticket for Dick?s show and targeted advertisement. Hilariously, the complaint also alleges that fans of Maddox are likely to mistake Madcucks for the real Maddox. Finally, Dick & co. are accused of ?directing targeted harassment? toward the sponsors of Maddox?s new podcast (and once again, no proof is provided ? only screenshots of fans lamenting some questionable language by someone on Maddox?s podcast network).

Relief requested: 20 million dollars; the injunction; placement of all of the servers and equipment from Dick?s company under protective order.

Intentional infliction of emotional distress

This claim is usually quite difficult to prove ? and much more so if, as is the case here, there is no proof whatsoever (not even a psychologist?s bill) of the monetary damages that the two plaintiffs incurred from being made fun of on the internet as they tried to get the defendants fired or defunded.

Relief requested: 20 million dollars, plus another 20 in punitive damages.

Tortious interference with a contract and business relationship

Maddox and Jess allege again, on no proof, that the defendants procured a breach of contract with Maddox?s sponsors; that they harmed the sales of his latest failed book; and that they ?interfered? with Maddox?s fans.

Relief requested: $2M in damages and $10M in punitive damages.


Here the plaintiffs accuse the defendants of ?stealing? Maddox?s ?property? including a list of fans, sponsors, and phone numbers, and of ?transferring? that property to thousands of Dick?s fans (again, the closest thing to a proof listed in the complaint is the 867?5309 joke).

Relief requested: 20 million dollars, plus another 20 in punitive damages.

Deceptive acts, misleading business practices, false advertising

For unknown reasons, Maddox (a California resident) claims he should be protected under the ?consumer protection act? of New York ? perhaps as a consumer of Dick?s podcast, although the reasoning is far from clear ? against the ?harassment campaigns? from the defendants.

Relief requested: 20 million dollars, the injunction, and the sequestration of the servers and equipment of Dick?s company.

Now we come to the claims against Asterios?s employer Weber Shandwick (?WS?) and their lead counsel.

Negligent hiring, retention, supervision, infliction of emotional distress, and general negligence

The lolsuit alleges that ?an individual named ?Heather?? (who we will later find out is actually Maddox himself) emailed high-level female executives at WS, sending the first email in the chain only one day after the Cuckmas Carols album is published on iTunes.

Image for postThe author of ?The Alphabet of Manliness? posing as a female journalist/activist and e-mailing female executives at WS and AT&T to try and get Asterios fired (excerpts; read the full email chain here)

In the emails, Maddox pretends to be a female journalist named ?Heather S.? working for Cond Nast (which he misspells), the parent company for Vogue, Vanity Fair, GQ, and other popular publications.

?Heather? says ?she? is writing a story about online harassment, and then proceeds with a shameless hit job on Asterios. ?She? quotes satirical statements from Dick?s website, taken out of context, to try and make it look like Dick advocates for rape. Then, ?she? proceeds to state that Asterios is associated with Dick, is ?taking part in an online harassment and bullying campaign,? and ?uses alt-right phraseology like ?cuck.?? ?She? asks whether WS will hold Asterios ?accountable? (incidentally, any Asterios fan is sure to know he is outspokenly liberal and the furthest thing from ?alt-right?).

The lead attorney for Weber Shandwick answers, asking ?Heather? to identify ?herself? before they speak on the record. ?Heather? makes up hilarious excuses (?I?m on an assignment in London?) and ? perhaps learning from the restraining order ? provides no other personal information, while still attempting to get a list of the companies Asterios has worked with in the past.

Image for postThe author of ?The Alphabet of Manliness? posing as a female activist and requesting a list of companies Asterios has worked with so they can ?hold him accountable? (excerpt; read the full email chain here)

Now, Maddox is suing WS and the lead attorney for not firing Asterios and not protecting Maddox from further harassment (even though WS had no such duty to him and had no clue how Maddox is even involved, since the emails didn?t mention him at all). It?s also alleged ? you guessed it, without a shred of proof ? that Asterios recorded the Cuckmas Carols album using Weber Shandwick?s equipment and technology.

Relief requested: 80 million dollars in damages.

Finally, we come to and their customer service representative.

Negligent failure to warn, fraud, promissory estoppel

At this point, readers shouldn?t be surprised that Maddox also repeatedly e-mailed, the platform that Dick uses to fund his podcast, to try and get his account suspended (all while complaining in the suit that he was the victim of a harassment campaign that took away his sponsors).

Maddox and Metal Jess are suing Patreon because ? and I won?t pretend to follow the ?logic? here ? Patreon failed to warn them of the ?threats? they had received from Dick and his followers on Patreon (no proof), even though Maddox was the one who informed Patreon in the first place.

Image for postMaddox sues Patreon for failing to warn him of what he warned them about (pp 47?48 of the lolsuit)

For good measure, Maddox and Jess are also suing for fraud because the customer service representative who answered Maddox?s complaints ?made multiple material misrepresentations or omissions? to Maddox (even though it appears he simply told him he?d forward the communications to a dedicated ?trust and safety? team within Patreon).

Last but not least, Patreon is being sued for promissory estoppel ? an extremely hard claim to prove that involves breaking a promise that the damaged party relied upon to their detriment ? because the customer service representative allegedly ?promised to do something? but evidently did not because Patreon never banned Dick from their platform.

Relief requested: 20 million in damages.

Deceptive trade practices

The entire claims section is just three paragraphs that simply mention unspecified deceptive ?representations, or practices? likely to mislead consumers acting reasonably, as well as participating in a ?deceptive scheme? against Maddox, namely to pocket the usual 5 percent fee from the money pledged to Dick Masterson through Patreon.

Relief requested: 20 million in damages, 20 million in punitive damages, a court injunction for Patreon to take down Dick?s, Asterios?s, and Madcucks?saccounts and disgorge all of Patreon?s profits incurred from those accounts.

The Aftermath

The reaction from Dick and his fanbase is equal parts bemused and outraged.Episode 77 of The Dick Show, the first after Dick was served, is well worth listening to. The fan community starts creating an avalanche of hilarious songs and comedy bits around the lolsuit.

All defendants (minus Madcucks, who was never properly served) hire lawyers and submit their motions to dismiss the lolsuit. As Maddox?s side responds, it becomes increasingly clear that Maddox did not write the original complaint himself (as everybody was assuming) and that, somehow, an actual licensed attorney wrote that absolute gem of a complaint.

Thus begins the legend of Kevin Landau, referred to in the Dick Show community as a dogbite lawyer (because his profile lists ?animal and dog bites? as part of his practice). His document submissions, with their perusal of apostrophes and questionable legal theories, become a great source of hilarity for the entire Dick show community.

The first filing by Landau after the original complaint is a proposed default judgment against Asterios. The document claims that the time for Asterios to respond to the lawsuit has expired, and that he should therefore be found guilty, pay $20 million to the plaintiffs, and never be allowed to mention Maddox?s or Jess?s names ever again. There?s just one small hiccup: Landau filed this document a full month before Asterios?s answer was actually due.

Landau?s brother then sends an email to Jordan Greenberger, Asterios?s lawyer, offering to withdraw that motion ?in the spirit of cooperation? in exchange for $2,545 in ?fees.? Greenberger obviously refuses.

Image for postMaddox?s lawyers offer ? ?in the spirit of cooperation? ? to withdraw their frivolous default judgment motion (filed a month early) for $2,545 (source)

Because of the nature of the claims and the absurd amounts in damages requested by Maddox, the lolsuit is transferred to New York?s Commercial Division, which should speed up the proceedings.

The defendants file motions to dismiss. Many of the lawyers take jabs at Maddox, often referring to ?bald accusations,? tearing the suit apart, and showing various degrees of disdain for Landau. Many of Landau?s arguments are hilarious, including the one below about the harassment endured by Metal Jess (keeping the restraining order in mind):

Image for postThe only reason Metal Jess is being targeted is ?because she is a beautiful African American woman? (page 7 of reply to Dick?s motion to dismiss)

The reply brief from Greenberger, however, outstages everyone by spelling out APOSTROPHE, CUCK, and LOLSUIT with the first letters of each paragraph and by stating that Asterios intends to prove that Maddox is actually a cuckold (claiming truth as an absolute defense to defamation).

Image for postAsterios intends to prove that Maddox is, by his own dictionary definition, ?a cuckold? (page 8 of Greenberger?s reply brief)

In another stroke of genius, Landau grabs an obviously satirical post by Madcucks, cuts out the portions of the post that make it look like satire, and uses it as genuine admission that the Madcucks character was created in secret by Dick and Asterios during an hours-long conference call, using unspecified ?technology? from Dick?s company.

Public documents emerge revealing that Landau has been arrested for DUI and has, installed in his car, a court-mandated ignition interlock device (meaning he has to blow into a breathalizer before he can start his car, and periodically pull over and test his breath again while driving). According to the documents, Landau also failed a rolling test on the first day the device was installed. Landau is now reborn in the Dick Show lore as LanDUI.

The 120 days limit for serving Madcucks with summons passes ? he is cleared and no longer a defendant in the lolsuit.

Landau files yet another brilliant motion for a temporary restraining order to prevent all defendants, as well as all Dick Show fans and the entire world, from making fun of Maddox and Metal Jess. He withdraws it a few days later.

Only after all defendants have exhausted their motions to dismiss and are waiting for judicial intervention, Maddox files a sworn affidavit in which he finally reveals he was indeed ?Heather S? ? the Cond Nast journalist trying to get Asterios fired ? despite previously claiming under oath that he was not. Around this time, Maddox starts hosting a weekly news program on YouTube.

Image for postMaddox, author of ?The Alphabet of Manliness,? admits to impersonating a woman online (page 6 of an affidavit filed on March 8, International Women?s Day)

The lawyers for Asterios and his employer put Landau on notice, stating he must notify the judge that Maddox has committed perjury by filing contradicting affidavits, and has also admitted to criminally impersonating a journalist in an attempt to cause financial damage to Asterios.

Rather than complying, Landau gives the two lawyers ?24-hours to recant this nonsense? and then, less than 24 hours later, files a motion for sanctions against the two lawyers claiming that they threatened criminal prosecution only to gain an advantage in their case. Landau also denies the obvious, stating that Maddox somehow did not perjure himself and is not guilty of criminal impersonation.

Image for postLandau?s biting letter to the attorneys for Asterios and his employer accuses them of having put on ?a pathetic display of lawyering? (source)

The two lawyers have now filed a cross-motion for sanctions to both the plaintiffs and Landau for his frivolous conduct. A hearing is scheduled for mid May? and this is where we are so far in this very ?special? lawsuit!

Closing Notes

Most defendants might get their claims dismissed early because they don?t live in NY, but Asterios Kokkinos does. He was burdened by medical expenses before this, and his legal fees in defending against this ridiculous suit are already close to $25,000. As Popehat?s Ken White has said on this case, these types of lawsuits are cheap to file but ruinously expensive to competently defend. This is doubly the case when a suit is filed in expensive New York.

Part of the legal strategy for Weber Shandwick could be to distance itself from Asterios. To their merit, they have not done so thus far and there is no indication that they intend to or will. However, the possibility remains that Maddox?s smear campaign might damage his future job prospects at the company ? if only because he?ll be known as ?the guy who got sued for hundreds of millions of dollars? to people unfamiliar with the matter.

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