It has been my thought all along that dealers who made the video would not have gone to media first. I don't believe that would have been the first play. I believe the video was originally made to extort money out of Rob Ford. Dealing with the media brings a lot of risk - first off they would be dealing with some very sharp journalists and there is also the potential that the media would not have the funds to pay for the video (which is exactly what they found out). Whereas, they would know that Rob Ford is sitting on a family inheritance, that he would be horribly compromised by the existence of the video, and that ultimately he is a buffoonish simpleton.
I would be willing to bet just about anything that their first play was to extort Rob Ford for money in exchange for not releasing the video to the media. How that played out is anyone's guess, but we can speculate... could be he met their demands and paid them off, then they double-crossed him and decided to try to get a second payday out of the video. Or, it could be that they dropped the extortion attempt on Ford, and then tried to get money out of Gawker and the Star. What would make them drop an attempt to squeeze some money out of Ford? Well, 2 dudes in photo were shot (one dead)... We already know that Ford has no qualms about sending out his goon squad to try to retrieve the video, as evidenced by Lisi and Price's actions after the Star/Gawker story broke...
One thing that has bugged me since Project Traveler is the fact that the shooter in the Anthony Smith case was rapidly processed with a highly unusual plea down to manslaughter. At first I thought this smacked of cover-up, but what if the deal was given in exchange for the shooter to turn states-witness? To testify on who called in the hit in the first place?