By Jeff John Roberts
August 4, 2015

It’s been a hell of a month for Heather Dietrick, even by the standards of the mud-slinging, gossip-soaked world of Gawker Media. I caught up with Dietrick, who is the company’s general counsel and president, in early July shortly before a slated $100-million trial over a Hulk Hogan sex tape, and then again after Gawker nearly imploded following an ill-advised story it published about a man seeking to hire a male escort.

Take a minute to watch the short video above, which shows Dietrick narrating the Hogan saga so far. It reveals her as someone who is smart, confident, and imposing—and suggests she doesn’t think for a second that, despite her relative youth, she might be in over her head.

“It’s a story I hold my head high in fighting. We told a real story that cleared a lot up about what was out there. Hogan himself was out there talking in color detail about his sex life again and again and his interaction with women in the bedroom again and again,” said Dietrick, explaining why Gawker published a grainy excerpt of a tape showing the wrestler having sex with the then-wife of his friend.

Her point is that celebrities wield a lot of power in society, and many use the media to puff up their fame, but only on their terms. Dietrick believes it’s the job of outlets like Gawker to tell celebrity stories the way journalists want to recount them, and the way the public wants to hear them.

But why, in the Hogan case, did this extend to publishing his sex video? Why must Gawker’s view of free speech extend to showing people with their clothes off?

Dietrick’s answer is that the video serves to prove Gawker’s source material. Without it, Hogan could have continued to refute the tape’s very existence. Indeed, that’s what occurred when Gawker, in another of its major exposés, revealed that the former mayor of Toronto liked to smoke crack; the mayor denied the charge, and threatened to sue Gawker until the police confirmed existence of the tape.

These sort of episodes often involve Gawker going out on a legal limb all alone since most newspapers—which won so many free speech fights in the 20th century—can no longer pay for litigation, and other digital media outlets have yet to take up that torch.

For Dietrick, who always aspired to be a First Amendment lawyer, the Hogan fight is also a career-making case, since losing the wrestler’s $100 million privacy claim could mean Gawker will fold. But for now, things are looking up since the recent leaks of Hogan’s racist rants appear to validate the publication’s position that publishing its tape excerpt was newsworthy. (The trial has been moved back to March).

Despite the halo from its free-speech crusades, however, Gawker must also wear the stigma of its moral mistakes—including the decision to ruin the life of a married Conde Nast executive by publishing his attempts to buy a male escort. Gawker was pilloried for the story not only because the executive was not a public figure, but because it became complicit in the escort’s attempt to blackmail him (the escort had warned the executive he would go to the media unless he tapped his politically-connected brother, and Gawker helped the blackmailing escort—whose identity it concealed—make good on that threat).

“I was extremely uncomfortable with the post as an editorial post,” Dietrick told me last week. “I believe it’s a newsworthy story that’s legally defensible, though we didn’t do the story in a way we want to do going forward.”

She added that she and many others regretted that the story was published, but that she disagreed with owner Nick Denton’s decision to take it down, and would have elected instead to add text to the top of it in order to explain the mistake in judgment.

The decision to take down the post triggered a meltdown among the editorial staff, and led a gaggle of writers and editors to leave. But Dietrick, who like many others at Gawker owns shares in the company, says the organization is now “back to calmer waters and business as usual.”

Gawker’s future is now up in the air as it strains to reinvent itself amidst a rapidly changing and consolidating media field. But, for now, Dietrick is likely to stay busy helping Gawker navigate legal fights that other publications can’t or won’t take up.

An earlier version of this story incorrectly said the Hogan trial had been moved to September; it will take place in March.

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