LOS ANGELES – Norm Zada and Perfect 10 finally got in over their heads. A district court judge has ordered all assets belonging to Perfect 10 be liquidated to satisfy a $5.6 million judgement levied against the company after it filed one too many frivolous copyright-infringement lawsuits.

The lawsuit that broke the camel’s back dates to 2011, when Perfect 10 accused Usenet newsgroups access provider Giganews of direct and contributory infringement by allowing users to upload images owned by Perfect 10 and neglecting to remove the images when notified. In 2015, a judge sided with Giganews and ordered Perfect 10 to pay Giganews’s more than $5 million in attorney fees and costs. Perfect 10 appealed the decision in 2016, challenging the central issue of “safe harbor” as defined in the Digital Millennium Copyright Act. In February 2017, the court found all of Perfect 10’s arguments in the case lacked merit and upheld the previous judgement.

Perfect 10, ostensibly a men’s magazine and website, rightly could be called the first copyright troll. Since at least 2002, Zada has pursued a string of lawsuits — numbering 20-30 at last count — alleging unlawful use of the publication’s images. In fact, since he shuttered the magazine in 2007 claiming copyright infringement made continued publication unprofitable, filing copyright suits has been Zada’s primary business (though the website Perfect10.com still exists).

Zada’s targets usually were big companies with deep pockets. In addition to Giganews, Perfect 10 sued Google, Amazon, VISA, Tumblr, Microsoft, CCBill, LeaseWeb, iBill, Internet Key, RapidShare, DepositFiles, Yandex, French hosting company OVH and Megaupload. Though a few of the defendants settled to dispense with the nuisance (notably Megaupload), Perfect 10 lost most of the cases — most notoriously, the suit against Google.

Along the way, though, the lawsuits generated some good legal precedent for concepts like intermediary liability and helped to clarify what the DMCA means by “safe harbor.” The Google case, for example, which hung on Google’s caching of images to display in search results, established the notion of transformative protection under copyright law.

The end of the story is sad, in a way. A former professor, professional poker player and hedge-fund manager, Zada earned a PhD in computer science and worked for IBM before founding Perfect 10 in 1997. His initial goal was to publish “a classier Playboy” featuring only all-natural women.