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Thucydides said:Indeed, although my campaign was more of a "how not to" exercise. The advantage for non establishment politicians today is there is a far greater access to non traditional channels for getting the word out than back in 06, although that cuts both ways; the "elites" can pay to have their messages pushed to the top of Google and probably manipulate other social media channels as well. Of course the person who defends everything defends nothing, so diverting dollars from traditional campaigning may be a good thing.
Hatchetman
I would also suggest that your friend researches and does the numbers. Although the political class is loath to talk about numbers, and will go to dizzying lengths to change the subject (or if pressed compare apples to building material), this is an effective tactic. Both Mayor DeCicco and then challenger Joe Fontana started their campaigns with an emphasis on Toronto garbage being trucked down the 401 as their key campaign issues, by doggedly sticking to the numbers both of them eventually changed their tunes as the campaign progressed, and discussions about finances and taxes were high on the list towards the end (although not as much as I would like, and certainly not enough to sway the election, otherwise I wouldn't be writing to you on Army.ca now! ). You might not see any real effect in the campaign world (the Media faithfully stuck to the "narrative" in London, and I think they might actually have been puzzeled and even a bit annoyed that the "narrative" was changing from underneath them).
And of course cultivating legacy media is a good thing in Toronto, where there is a large media market and it is harder to get shut out. He might be able to get a reporter, talk show radio host or (low probability/high payoff) TV personality interested in following his campaign. I managed to get two talk show hosts to give me more than cursory coverage because I could supply a good sound bite and sounded halfway intelligent on their call in shows, skill sets your friend should start working on now. Practicing for ambush questions is also a skillset to be developed. While I doubt your friend or most people in his circle have the issues Rob Ford has, a detailed life review by your friend and his inner circle of advisors is probably desirable. You know the press and opposition are going to do this, be prepared. I suspect that now even relatively trivial events (parking ticket, controversial letter to editor, indescreet social media faux pas) could be vacuumed up and held as ammunition to make things difficult, and set your friend back on his heels (especially if he is gaining any traction).
Other lessons learned is to boil your campaign down to an "elevator pitch" (i.e. can you explain your campaign in the time it takes an elevator to go up or down a floor). Sadly for people like myself who like discourse, most people don't and are unwilling or unable to sit down for a big, detailed pitch of how he is going to change Toronto.
Trust me we have been discussing alot of this for over a year (quick sound bites, hard details, responding to loaded questions etc) now (almost 2 really) It started off more as a joke between our circle of friends, but has gotten more serious, and I have on numerous occasions (especially when he and others pointed out Ford's earlier and seemingly minor now, trangressions) pointed out his own past, and done the hypotheticals... 48th Regulator is on my Facebook (probably doesn't realize though), he can see some of the battles we refer to as "Thunderdome". But I will still pass on your advice , thanks.