Nick Denton has lost another round to Hulk Hogan.

The Gawker Media founder sought bankruptcy court protection Monday in New York, after a Florida judge refused to halt enforcement of a $140 million damages award in pro wrestler Hogan’s invasion-of-privacy lawsuit.

Gawker itself filed for bankruptcy June 10, a move that temporarily put the brakes on Hogan’s efforts to collect on the verdict he won after the online media company posted excerpts of a sex-tape featuring him. Denton was also a defendant in the suit and liable for the damages award.

Denton filed an emergency motion seeking to stay enforcement of the verdict against him pending appeal, but the judge in the Florida case on July 29 refused. Denton has said that allowing Hogan to collect the crippling verdict while the case is on appeal is a threat to the freedom of the press.

The Chapter 11 petition filed Monday in Manhattan federal court listed assets of $10 million to $50 million and liabilities of more than $100 million, including Hogan’s claim and other pending lawsuits.

Thiel Victory

Denton’s bankruptcy filing may be seen as a victory for Peter Thiel, the PayPal co-founder who bankrolled Hogan’s lawsuit.

According to Gawker, Thiel has had it in for the company since 2007, when it outed him as gay. Thiel, who sits on the board of Facebook Inc., has since publicly acknowledged that he’s gay and called Gawker’s now-defunct blog Valleywag the “Silicon Valley equivalent of al-Qaeda.”

In a May New York Times interview, Thiel described his backing of Hogan and other litigants as a philanthropic way to help those who can’t afford to defend themselves against press attacks and intrusions.

Thiel didn’t immediately respond to an e-mail requesting comment on Denton’s filing.