Many heads have been scratched since last month's Republican National Convention, when something strange happened. During the climactic final night of the event, Silicon Valley tycoon and Facebook board member Peter Thiel appeared, seemingly out of nowhere, to out himself as a leading supporter of Republican presidential nominee Donald Trump.
In the few short weeks since, the head-scratching grew quite a bit harder. Why has Thiel, practically alone within the rarefied class of high-tech billionaire sophisticates who claim citizenship in the U.S., continued to support a presidential candidate who appeals directly to the emerging "alt-right" white nationalist electorate?
The media, Peter Thiel and Donald Trump
Only Peter Thiel can answer that question. In the meantime, though, Thiel's role as the not-so-secret-anymore funder behind the notorious Hulk Hogan "sex tapes" lawsuit that bankrupted Gawker Media provides one key point of commonality between himself and Trump: both men are self assigned policers of "media bullies."
In Thiel's case, that has taken the form of destroying a media organization that criticized his business practices. Though he attributes the Gawker lawsuit to personal privacy issues, Gawker Media's previously defunct Valleywag branch was a persistent, if tiny, critic and lampooner of Thiel, and Gawker itself drew repeated attention to the massive failure of Thiel's hedge fund, Clarium.
On his part, Trump has loudly and frequently complained that he is the victim of negative press, and he has become notorious for booting reporters out of his campaign events.
Rather than destroying existing media platforms, though, it seems that Trump has formulated a plan to establish one of his own.
Political observers are beginning to gather evidence that Trump is planning to create a media organization that will outflank anything currently existing on the right wing.
That theory has gathered steam in recent days, following the recruitment of Steve Bannon (of Breitbart News) and Roger Ailes (of Fox News) to the Trump campaign.
Charles Harder and the media
That brings us to another important point of commonality between Thiel and Trump: the attorney Charles Harder. If the name doesn't ring a bell, join the club. Harder worked in relative obscurity until this past May, when he edged into the media spotlight as the lawyer who received a reported $10 million stake from Thiel for his services in the Gawker lawsuit.
In June, Harder popped up again as the legal force behind Trump's "Hairgate" letter to Gawker. The letter demanded an apology for an elaborate investigation of Trump's notoriously unique approach to hair styling.
Now it appears that Trump -- and by extension, Thiel -- have upped the ante considerably.
As reported by Politico, earlier this week Harder sent a notice on behalf of Trump's wife Melania, threatening to sue the Daily Mail of the U.K. for publishing a somewhat salacious piece about her past career.
According to Politico, Harder also threatened action against Inquisitr and BipartisanReport, both of which have already apologized for re-publishing the Daily Mail report. Later this week, Fortune Magazine added two another media organizations, The Week and Liberal America, to the Melania Trump lawsuit list.
Be careful what you wish for, part deux
Ironically, the lawsuit threat may come right back to bite Donald Trump -- and by extension, Thiel.
Liberal America is a niche organization that no-one seems to have heard of until it appeared on the lawsuit list. Now that it got a mention in Fortune, it is probably experiencing an uptick in traffic.
Liberal America is among the organizations that published an apology for repeating the Melania Trump story, but it did so "under duress." If you're curious about exactly what that means, the Liberal America apology appears under the somewhat unapologetic heading, "Trump Lawyers Said Melania Didn’t F**k For Money, Forced Us To Apologize, So Here It Is."
In case anyone missed the Daily Mail piece about Melania Trump, the apology provided Liberal America an opportunity to repeat, point by point, all of the allegations that appeared in that publication.
As for Peter Thiel, the Harder letter provided both Fortune and Politico with an opportunity to rehash the Gawker case for anyone who missed that.
Thiel has already been roundly criticized for his role in the Gawker case, particularly so because of his status as a Facebook board member. Politico is a niche organization that appeals mainly to political junkies, but Fortune is a mainstream business publication and a legacy from the heyday of printed media.
Fortune seems to have taken special care to rehash the Gawker case in gory detail, winding up by noting what may be the ultimate irony:
After the judgment was handed down, Gawker filed for bankruptcy protection, and last week its assets were sold to Univision for $135 million.
That's right, Thiel won the battle but now Univision has picked up the Gawker mantle. Though the company reportedly will not continue Gawker as a standalone site, industry observers attribute Univision's acquisition of the rest of Gawker Media's sites to a push for grabbing, and holding, new and younger audiences across a range of topics including the tech website Gizmodo.
That demographic is not particularly attracted to Trump's white nationalist messaging, and as a Spanish-language media powerhouse, neither is Univision.
It's also worth noting that Univision is co-owned by Haim Saban, who is a chief financial backer of Hillary Clinton's bid for the presidency.
Trump, Thiel, Clinton and the alt-right bombshell
The media angle has revealed some interesting points of intersection between Thiel and Trump during the course of the campaign...and there is so much more.
Earlier this week, the Clinton campaign announced that her upcoming speech in Nevada on Thursday will directly address the "disturbing connection" between Donald Trump and white nationalism.
That announcement gave the Washington Post, for one, a golden opportunity to comb over the origins of the extremist alt-right movement:
The alt-right began with a speech the conservative writer Paul Gottfried gave in 2008, after the Republican Party's electoral wipeout. Gottfried called for an "alternative right" that could defeat "the neoconservative-controlled conservative establishment." That idea was soon adopted by the “identitarian” nationalist Richard Spencer, who founded an Alternative Right website, but it was also claimed by supporters of Ron Paul and conservatives who opposed multiculturalism.
If you are a regular reader of Triple Pundit, Ron Paul and Peter Gottfried will ring a bell or two.
Peter Thiel was the chief financial backer of Ron Paul's failed presidential bid in 2012.
Thiel also happens to a scheduled speaker at the upcoming Property and Freedom Society conference in Turkey next month, an organization that featured none other than Paul Gottfried at its inaugural meeting.
It looks like Thiel better be prepared to duck on Thursday, or he might get hit by whatever bombs Clinton is preparing to lob at Trump.
Stay tuned.
Photo (cropped and altered): via Sportsfile Web Summit on flickr.com, creative commons license.
Tina writes frequently for TriplePundit and other websites, with a focus on military, government and corporate sustainability, clean tech research and emerging energy technologies. She is a former Deputy Director of Public Affairs of the New York City Department of Environmental Protection, and author of books and articles on recycling and other conservation themes.