“Do I look like that?” Nick Denton demands with a grin, when asked if he’s losing sleep over Hulk Hogan’s $100 million sex video lawsuit.

The founder of Gawker Media—who, by his own estimate, has been spending “hundreds of thousands of dollars a month” on lawyers in the run-up to a July 6 jury trial in a Florida state circuit court—does look like he hasn’t bothered to shave for the past few days as he sits in a windowless conference room at his company’s headquarters in Manhattan’s Nolita neighborhood.

“This,” the 48-year-old Denton retorts, “is as close to shaved as I ever am.”

Regardless of the outcome of the scheduled 10-day trial in St. Petersburg—best known as a retirement community in Florida’s southern Pinellas County where Denton’s sardonic flagship blog has few loyal readers—the British-born, Oxford-educated Web entrepreneur is about to experience the closest shave of his life.

Worst case scenario: Hogan, a 61-year-old actor, product-endorser, musician, and former reality show and World Wrestling Federation star—whose given name is Terry Gene Bollea, a favorite son of Tampa, across the bay from St. Petersburg—prevails with a jury of his peers.

Denton’s privately-owned company, which has grown to 300 employees in five countries since its modest launch in 2004 and boasts more than 100 million unique visitors to its eight separate blogs and an estimated $7 million in profits on $45 million in revenue, could go belly-up.

Even if the jury gives Hogan a fraction of his claim, and even if Gawker ultimately wins on appeal, Florida law would require Denton to post the full amount of the award pending the final disposition.

Denton—who owns, through various family trusts, 68 percent of Gawker Media, a private company said to be worth around $200 million—understandably doesn’t want to even think about that. “Let’s get through the trial before we start game-playing the bond,” he says.

“There’s a one in ten chance of disaster,” he says, giving odds on his corporate demise. “The way I look at it, it’s a five in ten chance that we come through this stronger, and four in ten it’s a wash. Only one in ten bad.”

Denton is an old hand at being sued; Gawker regularly receives demand letters from the attorneys of aggrieved celebrities, and occasionally the company has settled cases with substantial payments—the cost of doing business as a “bold and brave” news outlet, as Denton likes to describe Gawker.

And if now he’s confronting an existential threat, one would hardly know it from his demeanor of jaunty sangfroid during an aggressive campaign of pre-trial persuasion in the court of public opinion.

Indeed, for an article in Sunday’s New York Times—one of several, including this one, in which Denton has argued his case in advance of Florida Circuit Court Judge Pamela Campbell, a Jeb Bush appointee, gaveling the trial to order—he was relaxed enough to smoke a joint in front of a reporter.

In the state of Florida, where Denton hopes to convince a jury of his seriousness as a journalist and the rightness of his cause, possession of more than 20 grams of marijuana—that is, less than an ounce—is a third-degree felony.

(Irony of ironies, considering that Denton sees one of Gawker’s core missions as exposing the private foibles of public figures, he was under the impression that the Times was too polite to note his fondness for weed. “He can’t use that,” Denton is quoted in the article, advising an amused colleague not to worry. “You can’t use that—I mean, realistically, in The New York Times.”)

Denton—who has lived in New York for two decades and says he hopes to become a U.S. citizen now that he is married to an American, actor Derrence Washington—delivers a rousing tribute to the First Amendment and the jury system.

“The Constitution of this country is clear,” he says, “and the people of this country hold up the Constitution in their hands like a sign of their patriotism. And people have a remarkable amount of common sense. Putting aside any First Amendment arguments, the common-sense arguments are pretty clear. ‘Dude, you’re a celebrity. That’s comes with a price. And part of that price is you’ve got to be discreet. Generally it’s good to be discreet if you’re fucking around, but especially if you’re a celebrity.”

Citing public comments, many of them graphic, that Hogan has made about his sex life during media appearances, Denton continues: “If you can’t even remember if you slept with Heather Clem [Hogan’s video sex partner] or not because there were so many brunettes that year, in the Internet Age you might once in a while have something come out if you’re going to be that indiscriminate in the pursuit of your celebrity perks."

The Hulk is seeking damages for loss of privacy, emotional stress and deprivation of his right to publicity, among other torts, over Gawker’s Oct. 4, 2012 publication of a 101-second highlight reel of the 30-minute video (made five years earlier without his knowledge or consent, and leaked to Gawker by an unidentified source) showing him naked, aroused and having sex with Heather Cole Clem, at the time the wife of his purported best friend, a Sirius Radio shock jock whose legal name is Bubba the Love Sponge Clem.

The lawsuit has been making its costly way through the judicial system for the past 2½ years, bouncing from federal court to state trial court to state appellate court and back again as each side’s high-priced teams of attorneys file motions, gather affidavits and depose witnesses.

Hogan initially sued Bubba, but dropped him from the complaint after the latter gave him the copyright for the video and apologized for his betrayal.

Bubba’s ex-wife Heather Cole—who, as conversation heard on the video indicates, had sex with The Hulk with her then-husband’s encouragement—remains a defendant along with Gawker, Denton, and A.J. Daulerio, the blog’s then-editor in chief who posted the video (which has since been taken down under court order) and his accompanying commentary.

Hogan’s lead attorney, Los Angeles legal eagle Charles Harder (an alumnus of zealous celebrity-protector Marty Singer’s Lavely & Singer law firm) claims Heather Cole is still in the case simply because Hogan has been unable to reach a settlement agreement with her.

But Gawker Media’s general counsel and president, Heather Dietrick, suspects that the other Heather, a Florida resident, remains a defendant simply to establish jurisdiction in the Florida judicial system, because it’s apt to be a more favorable environment for a home-grown celeb.

Denton sounds a hopeful note. The jury, he says, “is going to have to look at Hulk Hogan and Bubba, and they’re going to have to look at A.J. and me and the other people who represent Gawker. They’re going to decide who is honest, who’s telling the truth, and you don’t need to be a great legal expert to apply that litmus test. You can judge who is more consistent. Who was doing their job, and who wasn’t? Who was sticking to the values they espouse publicly and who wasn’t? Those are the sorts of questions that we welcome.”

In the pre-trial maneuvering, Gawker’s legal team—notably the Tampa-based First Amendment law firm, Thomas & Locicero, and the prominent Washington-based media firm Levine Sullivan—filed a 49-page brief in support of their request for Judge Campbell to summarily dismiss the lawsuit.

Aside from ample references to reports about the sex tape in the seven months leading up to Gawker’s posting (confirming the legitimate newsworthiness of the video, they argue) it was brimming with Hogan’s X-rated comments—on both the Bubba the Love Sponge and the Howard Stern shows, among other venues—concerning his sexual habits, his extramarital affairs, his penis-size, how and where he likes to ejaculate, and even the quality of his on-camera performance with the former Mrs. Clem.

During an Oct. 9, 2012 appearance on the Howard Stern Show, four days after Gawker posted the sex video excerpt, “Hogan explained that the sexual performance depicted on the sex tape,” Gawker’s brief recounts, "was not him at his most impressive: ‘I’m not trying to be a really pompous ass but…the situation I was in, I didn’t want to be overly aggressive’ because he was with his ‘friend’s girl.’”

On the same show, Hogan “repeatedly joked” with Stern about the sex video and his apparently massive member, the brief says. “Maybe instead of dropping the leg on people’s neck, I’ll start dropping something else on them,” Hogan quipped to Stern, according to the brief. Stern replied: “Drop those loads. That’s right.” To which Hogan, amid laughter, added: “Drop the tripod.”

Team Gawker’s argument was that given Hogan’s comfort with and participation in putting the video and intimate details of his sex life into the public domain, he could have no presumption of privacy, let alone sustain damages.

But in May Judge Campbell denied their request for summary judgment, without comment or explanation, and set the trial date.

"Judges, as a rule, don’t discuss pending cases,” a court press officer emailed The Daily Beast, in response to a request to interview Campbell, who in November was re-elected without opposition to another six-year term. "Doing so goes against the ethics of the judicial canon.”

Campbell, who otherwise has avoided the spotlight in a long legal career, was a central figure in one of Florida’s and the nation’s most controversial medical ethics cases, having achieved notoriety as the pro-bono lawyer for the parents of Terry Schiavo, who famously (and unsuccessfully) fought to prevent Schiavo’s husband and legal guardian from removing her feeding tube after a 15-year-long persistent vegetative state.

Meanwhile, attorneys for Hogan and Gawker are filing motions back and forth over what evidence should be admitted or excluded at trial. On Friday Team Hogan filed several briefs arguing that Gawker should be prohibited from introducing the wrestler’s many off-color remarks and other graphic evidence as “irrelevant” and “prejudicial” because they are not narrowly specific to the sex video, the target of Hogan’s lawsuit.

“Let me give you an analogy,” says Hogan attorney Charles Harder, arguing that while Gawker isn’t being sued for describing the sex video, the company went too far in posting it (never mind that Hogan initially sued Gawker for writing about the video as well, and Judge Campbell had granted his request for an injunction to delete Delaurio’s commentary before the state appellate court reversed her ruling and allowed it to remain).

“Erin Andrews, the ESPN reporter, was secretly filmed in her hotel room naked by a Peeping Tom,” Harder continues. "There were thousands of stories written about that, but nobody posted the video of her naked because she has a right to privacy in a private place, and she had a right not to be filmed.

“My client, Terry Bollea, was in a private place and he was secretly filmed. He has a right not to have that video posted, and it doesn’t matter if it was all 30 minutes or one minute and 41 seconds. No one had the right to show him naked.”

Of course, Hogan’s over-the-top, gamey public persona is wildly different from that of Erin Andrews.

When he takes the witness stand, there will be plenty to grill him about, says Gawker general counsel Dietrick. “I would guess his lawyers are advising him that there’s real risk here,” she says. “All this is airing out for everybody to see.”

Engaging in the time-honored technique of setting expectations, Denton, for his part, predicts Hogan will be formidable.

“He’s an extremely charming person who has been used to television, used to interviews, and he’s an American icon. So he goes into this process with a whole bunch of advantages. Unfortunately, his story is confused—and that will be exposed during the course of the trial.”