I'm not sure if it would be an ideal fit, considering the image and branding Okayplayer has manicured over the years.
In the same breath maybe the pigeonholing as a result of strong branding could be even more of a reason to at least entertain the idea of working with the Diplomats.
Secondly, like it or not there seems to be a crossed market here. People who have opinions on so called "True School" music are for some strange reason a fan or closet fan of the diplomats. Myself included.
Now if the main strategic vision of Okayplayer.com is to break artist of all types and break the notion of Okayplayer.com being a "Roots Site" or "Backpacker Site" then adding the Dips or experimenting with them can be the example you need to prove to others the legitimacy of your website as a promotional tool.
At the end of the day I could see it being a win win situation, where fans of both sides eventually become introduced to music they otherwise wouldn't.
If this is a joke, I would actually consider thinking about it for real.
Purple Haze THIS (Fill In Month)!! Or so I've been told for the past 1 year and a half.