Answer, write a blog about Gawker – do it well, show that you can write and it will end up on their radar.
Which after all is a repeat of Gawkers’ method itself: Write a gossip column where the initial subjects are other gossip columnists, hacks and flacks, then it will get noticed by the people who promote stuff. Down right PReditorial!
Flattery will get you everywhere.
Chris Mohney did just that, with arguably the longest ever resume:
Gawkerist: Nick Denton Finally Pays Us to Stop Blogging