As much as I'd like to see Dale beat Ford in court, it's actually a lose/lose.
What could be better for Ford at this point than being sued by a Toronto Star reporter? I hate to say it but that's the reality we're in. Yeah, a court would probably have police officers sitting there saying there were no pictures on the cell phone etc. but that won't be for months and months, assuming they don't settle. In the meantime, Ford gets to campaign with actual proof of how the media is out to get him. A reporter suing a politician is dicey enough but everything else about this plays into Ford's grand mythos of persecution, no matter how crazy that might sound.
The best part of the Conrad Black interview is where she asks him, since he's been sued for libel, if it isn't important for the interviewer to be responsible to for someone saying something libelous to them and he just goes silent for nearly 10 seconds trying to find the right way to squirm out of it. Fine, I'll grant him he's not a "real journalist" but that isn't a free pass to just ask him anything and let any response sail by uncontested because it's "his opinion."
I'm not a huge fan of Black but he's no idiot. He knows better than that. What if (to invoke Godwin's Law!) Ford said, "You know, I think Adolf Hitler had some really good ideas." ? Black would just go on to the next questions because that's Ford's opinion and it's not his job to debate him?