The problem with using Gawker is an example of the free press being silenced by thin-skinned rich people is that Gawker literally did this to themselves.
Even if you hate sites like Kotaku, Gawker had legit journalists working for them. But they were all undermined by the hubris of the executive brass at the company. They got told to take down the video, and Gawker told the judges to fuck off because "freedom of press & Hogan is racist" or whatever. Them being linked as a Trumpian attack on free press doesn't really work, since Gawker has never done any of the work that CNN, NYT, WSJ, MSNBC or WP has done. Gawker had numerous specialty journalist sites under its belt, but ran them like tabloids.
That said, there is a precedent being set here. Trump and his ilk are gonna take advantage of the public's sudden aversion to the press. But I think we should be less focused on the "who", and more on the "why". Why is the free press being attacked like this, what's the public benefit from it, and why does the public seem to support it?
I can at least get a handle on that last question. It's not that people suddenly hate the news, or believe that journalists are out to get them; it's more that people hate bad news on things they like, or bad news on things they don't understand. In a new world driven by social media echo chambers, right or wrong, people want their own biases confirmed... regardless if said biases are defended by reality or not. And since most of the press doesn't confirm their bullshit worldviews, they are seen as the enemy. Add Trump, a candidate that tapped into the resentment White Americans feel towards the media, intellectuals, social issues, women, & people of color, and you have a perfect storm. So, it doesn't really surprise me that the media is being attacked left and right, with Trump even implying violence being taken against news organizations he doesn't like.
But Gawker shouldn't be in the position of the victim here, when many other news organizations are way more deserving of that kind of defense.