Ha, a game of it! Why not?

The posts would have to be of substance, no points if someone just rambles on about nothing (or their day) for pages. Not that it needs to make logical sense, just be substantial. They would have to be grammatically correct and have proper spelling (to the extent you'd expect from an Advanced roleplayer), but it wouldn't need to be formal writing. 

How it might work: 
Jorick either writes a post or pulls up one of his own, and PMs it to you. You would read the post and create a prompt based on the post, then release it to the contestants at a predetermined time. 

Contestants then have a certain amount of time following that (say 12 hours) to write based on the prompt. Submissions would be PMed to you by the deadline, and then all submissions would be posted along with the winner. 

The goal is to have a blind test of long-windedness. It's not fair if folks see Jorick's post, they could easily out-wind him if his length is known.