I am less impressed by the cover letter's creativity than by its honesty. This guy writes like we're sitting together over coffee, or better yet, beer. He's either completely sincere or totally full of shit. After 5 minutes in person, it's probably easy to tell which.
If you click the last of the weird (and, imo, quite visually displeasing) yellow tab thingies, close to the scribbled-over piece of text, it says "You didn't think we'd give away our teammate's contact info so easily! [...]".
I interpreted this to mean that the guy who wrote the letter got hired by the ones who received it.
I'm the hacker in question and its the former ad I replied to. And yes, I'm quite gainfully and meaningfully employed with the Tribune. And no, I'm not full of shit (at least I wasn't on that occasion.) Glad folks are enjoying/inspired by it.
When I hear "creative cover letter" I think of something more than three to four paragraphs that cover an applicant's background, interests, and goals. It's an excellent cover letter, sure, but I fail to see much creativity with the form or structure. There's "only" the creativity that underlies all concise, punchy, effective writing.
Glad to hear this had a happy ending. Respect.