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==Legal troubles==
{{OR|date=September 2008}}
In 2003, Max posted on his website an account of his relationship with Katy Johnson, a former [[Miss Vermont]].<ref>[http://www.annoy.com/features/doc.html?DocumentID=100495 "Someone Talked"] Annoy.com account of Johnson's lawsuit vs. Max</ref> The story detailed Max's summer relationship with Ms. Johnson, and Johnson filed a lawsuit against Max claiming, among other things, an invasion of her privacy.<ref name="NYT">[http://select.nytimes.com/gst/abstract.html?res=F20E17FC39540C718CDDAF0894DB404482 New York Times - ''Internet Battle Raises Questions About Privacy and the First Amendment'']</ref> In response to the lawsuit, a Florida state court judge, Diana Lewis, ordered Max to remove the story from his website.<ref>[http://www.tuckermax.com/archives/images/Temporary%20Injunction.PDF TuckerMax.com: Temporary Injunction]</ref> Max and his attorneys removed the case to federal court arguing that the lawsuit implicated Max's First Amendment rights.<ref>[http://www.tuckermax.com/archives/images/TM%20Motion%20to%20Dissolve.pdf TuckerMax.com: Motion to Dissolve Injunction]</ref>. Max then asked the court to dissolve the injunction, arguing that the order was an improper prior restraint on Max's right to free speech. <ref>[http://www.tuckermax.com/archives/images/TM%20Motion%20to%20Dissolve.pdf TuckerMax.com: Motion to Dissolve Injunction]</ref> Max also asked the court to dismiss the claims asserted by Johnson.<ref>[http://www.tuckermax.com/archives/images/Tucker%20Max%20Motion%20to%20Dismiss1.pdf TuckerMax.com: Motion to Dismiss]</ref> The ACLU later filed a brief supporting Max's position that the injunction violated Max's First Amendment rights.<ref>[http://www.tuckermax.com/archives/images/ACLU%20Amicus.pdf TuckerMax.com: ACLU Amicus Brief]</ref> Johnson ultimately dismissed her lawsuit.<ref>[http://www.tuckermax.com/archives/images/dismissalnotice.pdf TuckerMax.com: Johnson's Notice of Voluntary Dismissal]</ref> The story was then re-posted on Max's website and was renamed "The (Almost Banned) Miss Vermont Story."<ref>http://www.tuckermax.com/archives/entries/date/the_almost_banned_miss_vermont_story.phtml#705 TuckerMax.com: The (almost banned) Miss Vermont Story</ref>
 
He was also sued by Anthony DiMeo III under the [[Violence Against Women Act]] in 2006 due to allegedly harassing posts on Max's internet [[messageboard]].<ref>{{cite web