Would Hunter Have Gotten Hired Today With That Letter?

Last week we published a letter a pre-famous Hunter S Thompson sent to the Vancouver Sun looking for work.

Thompson never worked for the Sun in his lifetime, so perhaps the cover letter didn’t work…on the other hand, the editor to whom Thomson had addressed his missive lasted less than a year in his position until he apparently offended everyone else he worked with and was demoted. So maybe there were more forces in play than it seems.

But would the letter work today? We polled a number of career and recruiting experts, including Ask A Manager‘s Alison Green, Ask the Headhunter‘s Nick Corcodilos, and Laurie Ruettimann of Punk Rock HR and now New Media Services. Here’s what they said… after the jump.

I think most employers are looking for someone who can make a point without alienating their audience. It’s not that they don’t respect directness, but in this context, when you’re approaching someone cold, it comes across as rudeness for its own sake. I think that trumps other qualities he brings to the table.

As an employer, how can you not think he would not be a huge pain in the ass?

I think there’s this attitude people have, that talent is everything and if you’re really talented you can be a prima donna, a jerk and it doesn’t matter. I think good employers have other things that they need to care about too, like whether you’re destroying their ability to retain other good people.

I would love to know what it was like to manage his work. I imagine he would work well in a situation where he didn’t need much management.


There’s a lot of integrity in saying he will only work with people he’s gonna get along with. I don’t think there are a lot of people who are willing to draw a line in the sand and say, “Screw off, I’ll find someone else. I think he was an unusual guy to begin wit,h and this was an unusual approach.

If i recieved a letter like that, given who I am, I would definitely call him for an interview. I would say, “Hey, cut the BS, what do you really like?” And then you have to figure out, does what he’s interested in doing fit with my operation? What he’s saying in that letter is, “I’m a pain in the ass to have working for you but I do a great job.” So the question is, if you do that good of a job, can I tolerate you? I would want to see some examples of his work. I would probably throw him an assignment and say, “Here’s a tough one, I’ll pay you for it unless it sucks.” If his production is really good, I might say, “OK, I have to have a beer with him and see, how bad can it be?”

Ruettimann (via e-mail):
In general, shock and awe doesn’t work. Recruiters are generally offended by the naivete of modern-day job seekers in this awful economy. And let’s face it—if you’re really as awesome as you say you are, you’re not sending a cover letter. You are using your network and walking into a hiring manager’s office without ever sending a resume.

So HST’s letter probably wouldn’t work for 99% of people out there. I like the principle of it, though.

And Joe Grimm posted his own take on Poynter.org:
Thompson also made it clear he might be what we call high-maintenance. This catch-all term covers everything from people who smash coffee cups against the wall, to despondent reporters who get writer’s block, to those who just peel the skin off everyone around them….

Would that letter have encouraged me to call Thompson and see what he had, or to set him aside for someone less challenging and less talented? I don’t know for sure, but I hope I would have been intrigued enough to take the next step. And that is the main purpose of submitting a cover letter — to get the editor to call you in for an interview.

Interviews have been condensed for clarity.