Silicon Valley tycoon Peter Thiel's continued support for Republican presidential candidate Donald Trump has been raising eyebrows since last spring, when he emerged as a designated Trump delegate during the primary campaign.

His most recent expression of support came over the weekend. According to the New York Times, Thiel is planning to make a $1.25 million donation to the Trump campaign. The Times reached out to a Thiel spokesperson and received -- you guessed it -- no comment.

Most players in California tend to swing Democratic, at least publicly. But Thiel continues to throw support behind the self-described success story who turned a gift from his father into a quarter of what he would have made in a mutual fund. In many ways, libertarianism is at odds with a sustainability agenda. While we believe in the value of business to power change, businesses require a robust regulatory environment in order to incentivize good action. Otherwise there is no business case for sustainability. But we digress ....

This follows the ringing endorsement of Trump's "you're fired" managerial style, which Thiel made in an op-ed that appeared in the Washington Post  on Sept. 6. The timing appeared designed to lay out the case that Trump would be fit to serve as commander in chief of the armed services, in advance of the Commander in Chief Forum televised by NBC on Sept. 8.

Since then, though, there has been radio silence from the Peter Thiel camp.

Last week, New York Magazine reported that it and several other news organizations have reached out to Thiel for some insight into the recent events roiling the Trump campaign. They did not receive a response as of this writing.

Thiel's reticence has not fully protected him from fallout from the Trump campaign. Earlier this year, political observers began to note Trump's proclivity for echoing fascist turns of phrase, an affinity apparently shared by Thiel. (Thiel was reportedly scheduled to speak at a conference affiliated with the white nationalist movement in Europe in September, but later reports indicated he withdrew.)

Another point of intersection with the Trump campaign is a nascent movement to repeal the 19th Amendment, in consideration of a gender gap that would provide Trump with a path to victory if women did not have the right to vote.

Here's what Thiel had to say about the 19th Amendment in a 2009 essay published in the Libertarian journal Cato Unbound:

"... Since 1920, the vast increase in welfare beneficiaries and the extension of the franchise to women — two constituencies that are notoriously tough for libertarians — have rendered the notion of 'capitalist democracy' into an oxymoron."

The editors at Cato received so much blowback that they provided Thiel with an opportunity to expand upon these thoughts in a brief follow-up published that same year. Here's the money quote:

"It would be absurd to suggest that women’s votes will be taken away or that this would solve the political problems that vex us. While I don’t think any class of people should be disenfranchised, I have little hope that voting will make things better."

That's hardly a reassuring take on democratic governance.

Thiel penned those words almost seven years ago. However, if he still doesn't think voting serves any practical purpose, now might be a good time to explain what other solution he has in mind.

That's an important question for a high-level Trump supporter, considering that the Trump campaign has also encouraged supporters to resort to violence because voting doesn't "make things better" if the entire election system is "rigged."

But like the saying goes, money talks. And it appears Thiel is still firmly in the Trump camp.

Paving the way for another Gawker lawsuit

Earlier this year, Thiel was revealed to have secretly funded the Hulk Hogan "sex tapes" lawsuit, which bankrupted the online news organization Gawker Media. Such an attack against a media organization that reported unfavorably on Thiel in the past is big concern for us at TriplePundit, since it amounts to a private assault on the First Amendment.  Now it seems Gawker is fighting back. In court papers filed last week, Gawker alleges that Thiel continued to interfere with its business even after it declared bankruptcy.

Peter Thiel justified his backing of the Hogan lawsuit by framing himself as a champion of the right to privacy against "media bullies." Now he faces the prospect of having to testify, in public, about the real motives that prompted him to target Gawker for extinction.

According to a report in Forbes magazine last week, the new filing is designed to gather enough evidence for Gawker to file suit against Thiel on charges that he purposefully sought to harm the company.

The legal basis behind the filing is something called Rule 2004: a bankruptcy proceeding that, in this case, would enable Gawker to examine the relationship between Thiel and several unsecured creditors, with the aim of determining whether or not they may cast their votes in bad faith.

The filing explains:

"As this Court is aware, one of the grounds for vote designation is a creditor acting with a motive to 'put the debtor out of business ... , destroy the debtor out of pure malice, or ... obtain benefits available under a private agreement with a third party which depends on the debtor’s failure to reorganize.'”

These unsecured creditors would include Hogan and at least two other persons with lawsuits against Gawker. According to the filing, Gawker has evidence to suggest these persons also received financial support from Thiel:

"If true, this indicates that three of the unsecured creditors are acting at the behest of Mr. Thiel. But Mr. Thiel is an individual who is not a creditor and who reports say is driven to a greater or lesser degree by a desire for revenge and the aim of putting the Debtors [Gawker] out of business."

Evidence suggests Peter Thiel steers activity

You can read the full 39-page Gawker filing on Document Cloud (posted by Forbes reporter Matt Drange). For those of you on the go, the filing lays out several specific instances in which Thiel apparently sought to undercut Gawker's efforts to settle its affairs after declaring bankruptcy.

Gawker alleges that after it declared bankruptcy, the activities of Thiel and his legal team were "arguably timed to affect the sales proceeds that [Gawker] could obtain in the auction."

One example is the cease-and-desist letter Gawker received from Thiel attorney Charles Harder last spring, "just days" after the media organization filed for bankruptcy. The letter demanded withdrawal of a story about Donald Trump's $60,000 hair treatment.

"At the least, these reports suggest that Mr. Thiel, who has no claim against the Debtors and is not otherwise a creditor, may be (directly or indirectly) controlling key aspects of these chapter 11 cases or otherwise be playing a large role in the economics of these cases."

Another example occurred in August, the day before the Gawker bankruptcy auction was scheduled, when an op-ed appeared in the New York Times under the Peter Thiel byline titled, "The Online Privacy Debate Won’t End With Gawker."

In the op-ed, Thiel attempted to link his funding of the Hogan lawsuit to the proposed Intimate Privacy Protection Act, an effort that was promptly slapped down by the bill's main sponsor.

The bankruptcy auction went forward and was a success after all, though -- as the Gawker filing alleges -- Thiel's legal team sent four cease-and-desist letters to the eventual buyer, Univision.

Gawker further alleges that the harassment of Univision continued into September.

All in all, Gawker concludes that these efforts, "while ultimately unsuccessful in foiling the sale to Univision, appear to have been aimed at undermining it."

Less privacy for Peter Thiel

The activity described by Gawker may seem like clear evidence of interference to a lay person, though according to a legal expert cited by Forbes, it's not likely that a bankruptcy judge would approve Gawker's request for testimony and documents. At the very least, a hearing would take place before there is a ruling on the motion.

In the meantime, the Gawker lawsuit is just one area in which Peter Thiel has opened himself up for scrutiny.

Image credit: Stephen Brashear (http://www.stephenbrashear.com) via flickr.com, creative commons license.