Senator Jerry Grafstein — known in the media as The Man Who Brought The Rolling Stones to Toronto (quite a feat, considering they’d only been here a couple dozen times before, and, of course, recorded a live album here in 1977, and then used Toronto as their regular rehearsal space for about two decades) — is thinking about grappling David Miller for the mayor’s chair.

“If I can’t find a viable candidate by Sept. 27, I will seriously consider it,” the SARSstock senator said at a Toronto International Film Festival party, as reported in the Toronto Sun on Sept. 12. “My wife, Carole, has been telling me to stop complaining and do something. I think I would win. A lot of people feel this way.”

Well, hello, snowflake. Welcome to hell.

You want to beat Miller? I’ll tell you how to beat Miller: he pulls a knife, you pull a gun. He sends one of yours — oh no, wait, that’s how you beat Al Capone. You want to beat David Miller? You’re on your own.

And I do mean on your own, since virtually every heavy-hitting political operative in the city, including Mel Lastman’s former fundraising guru Ralph Lean, has signed on to Miller’s re-election campaign. Maybe Grafstein (who, showing his unerring political instincts, backed John Nunziata in the 2003 mayoral race) can call on his buddies Warren Kinsella (who backed John Tory) and Dennis Mills (who was busy preparing to have his ass handed to him in the 2004 federal election by Jack Layton) and build on the momentum they have going after their anti-terrorist “We Are Not Afraid” day this past June. Remember that? No? Oh. Maybe Grafstein ain’t the man for the job after all.

But if you are crazy enough to run, Jerry, I do have one piece of advice: whatever you do, don’t kick off your maybe, maybe-not attempt to dethrone David the Goliath by saying something asinine like “I have lived here since 1955 and it’s in the worst shape I have ever seen it. It’s dirty and it’s not safe.” D’oh! You already said that? See, the thing is that by every conceivable standard of measurement, Toronto is safer than it’s been in decades, while litter is down by 40 per cent and Toronto is in the midst of a cultural renaissance (both street level and elite: uTOpia, meet Opera House), to boot. So the doom-and-gloom might be a hard sell.

But whatever the message, it’s going to be a hard slog trying to knock off the mayor anyway. Just ask Jane Pitfield, who’s resorted to begging the media not to discount her chances just yet. According to the Star last week, Pitfield unveiled her pledge to cut the fat at city hall in a press conference, saying, “Don’t prejudge and don’t underestimate me, because the best is yet to come. I have been waiting with relish for these nine months.” Coupled with the National Post clipping hanging in her campaign office window (next to the classy, handwritten “For Rent after November 15” sign) that says she likes herself a hot dog, supporters might be tempted to request that she put down the relish and the rest of the condiments and start running for mayor.

If you were to stake out Pitfield’s office (or live directly across the street, as your correspondent does), you’d have plenty of time to read the two — count ’em! Two! — lukewarm newspaper clippings posted in the window, since the office has never been unlocked or staffed as far as I can tell. Add to this the fact that her second campaign manager has just quit to “concentrate on his business” (replaced by admitted political neophyte Judy Paradi) and you start to wonder whether Pitfield is serious about running a legitimate campaign. Not that a legitimate campaign would put forward panhandling as a serious campaign issue. And not that a legitimate campaign would have spent nine months waiting with relish to get started.

A legitimate campaign would have started in January and relentlessly hammered away throughout the summer. That’s how Miller himself knocked off shoe-in Barbara Hall and establishment man John Tory back in 2003 (no one thought Miller had a chance until he pulled ahead in September).

A legitimate campaign would try to attack Miller from the centre, to appeal to both those who’d never vote for him and those who voted for him last time but are disappointed. A legitimate campaign would — fairly or unfairly — hammer Miller, who promised to clean up city hall, for untendered contracts at the TTC, a lack of progress on the waterfront and his ally Joe Pantalone’s tendency to have members of his family on the city payroll. A serious contender would also deliver something big and positive as the central plank in her campaign, rather than focusing on cutting spending. And a serious contender would not allow the mayor to turn the Conservative government’s recent bolstering of the island airport into a political whipping post — a contender would hold it up as evidence of the mayor’s inability to deliver on the one key issue of his last campaign.

Dennis Mills, whose name keeps getting batted around as a late-entry possibility, isn’t the guy, since he created the nefarious, airport-expanding Toronto Port Authority in the first place. Julian Fantino, who declined to enter the race, wouldn’t have been right, and the dirty war he and Miller would have fought — which Miller would have won — would have made everyone look ugly. Now it looks like Pitfield and Grafstein probably aren’t up to the job, either. It’s a pity. We could use a real race for mayor, if for no other reason than to get the important issues facing the city aired out. There’s still time to register. Any other snowflakes wanna brave the heat?

Originally published in Eye Weekly September 14, 2006.