Filing has begun for the 2009 city elections. Several of the odd-numbered wards will surely be engulfed in battles to decide new aldermen and Comptroller Darlene Green will likely face opposition in her re-election bid, but no race in the March primary will draw as much attention as Mayor Francis Slay’s attempt to win a third term.

Already Slay has drawn one Democratic challenger. Quite frankly, for someone practically guaranteed a challenger, this is the one his campaign advisers were perhaps most glad to see file, considering he defeated her by more than 20 percentage points just four years ago. A landslide by any measure.

Which is not to say Irene J. Smith is not a qualified and accomplished candidate. Besides being the former alderman of the 1st Ward, she is also an attorney and former municipal judge. But she does have her negatives too. She has never won a race outside of her 98% black northside ward. She didn’t fare very well with voters outside of north St. Louis in her 2005 race. And then there’s that peeing incident…

In 2001, during a filibuster of Slay’s controversial redistricting of city wards, which broke up the northside’s largest voting ward and critically damaged African-American political power, then-Alderwoman Smith was not allowed to leave the floor to go to the bathroom.

After many hours and continued refusal from then-Aldermanic President Jim Shrewsbury to allow Smith a bathroom break, she squatted over a trash can as supporters held blankets up around her.

Smith has for years maintained that she did not urinate behind those blankets… into a trashcan… on live television… and she successfully fought a misdemeanor public urination charge against her. But the incident was reported all over the world and the video was carried on national news, making the whole event one of the worst in recent St. Louis history, for many reasons.

In a 2002 guest column on TheCommonSpace.org, I wrote:

For me, Alderwoman Irene Smith’s action was a heroic demonstration of self-sacrifice, completely uncommon in this time and place. For me, and for most people I knew — black and white — the redistricting politics of a year ago were no more than an act of passive-aggressive bullying on the part of newly elected Mayor Francis Slay and his Southside political machine. This simple act of bullying would ultimately result in the weakening of black political power and the worsening of already poor race relations in a city known for its poor race relations.

I still believe that. Smith should forever be applauded for her sacrifice. But it should also be well understood how much she did sacrifice that day. Among those things was surely any chance at winning citywide election in the foreseeable future.

Her actions on that day will always be better appreciated among black northside voters than their white southside or central corridor counterparts. And that robs Smith of any chance of winning in the central corridor or having any kind of a respectable showing on the south side — components necessary to an African-American winning citywide election in St. Louis.

North St. Louis alone can’t elect a citywide officer. Using last month’s election results — certainly the highest African-American voter turnout on record — the northside’s 10 wards still just narrowly produced more votes for Democrat Barack Obama (about 100 more votes) than the southside’s 13 white wards, even though the north wards voted more than 98% for Obama (versus the southside’s 72%). The key is the five central wards. Call them “swing wards”.

St. Louis city remains one of the most racial segregated cities in America. The 10 northside wards are 93% black. The 13 southside wards are 80% white (with three over 95%). The city’s only hope of modern civility comes at its core. The five central wards are split roughly 51-43 black to white. And the three central-most southern wards also come close to that 50-50 ratio.

The formula to Francis Slay’s past electoral success has been a simple one: take all of south St. Louis (which has a higher population and therefore more voters), win 50+1 in central, and nevermind the northside. (Some would argue that not only does he campaign that way, but he also governs that way.) Hate it or love it, it wins elections.

The formula for an African-American candidate has been almost the exact inverse — almost: take all of north St. Louis, carry the central wards by a large margin (like 60%), and take a bite out of the southern base — particularly those southside wards with large black populations, like 8, 9 and 20.

This is why Irene Smith can’t win. Nevermind most voters don’t know her and she can’t raise enough money to fund a proper introduction in just 90 days, but the 2001 urination incident sours her chances with central voters.

So if not Irene Smith, than who?

The other most likely challenger is State Senator Maida Coleman. But can she win?

Yes.

Coleman certainly has her detractors, but her negatives are not nearly as high as Slay’s or Smith’s. She has a legislative career marked with accomplishments that can definitely be highlighted, including her time as the top Democrat in the Senate. She has been an outspoken critic against Slay and Governor Matt Blunt’s handling of St. Louis Public Schools. And as a woman, she would stand to become St. Louis’ first woman mayor — that prospect alone can help garner the attention of female voters in central and southern wards.

The challeges for Coleman will be that many people outside of her senate district (which includes almost half of city voters and travels far north and far south) aren’t aware of her. And there is that issue with a past bankruptcy which came out when she was mulling a run for state Treasurer a few years ago, but with the state of the current economy and people suffering throughout our city, Coleman overcoming her past financial troubles may actually endear her to voters.

The other possible challenger remains Slay’s biggest threat — License Collector Mike McMillan, the charismatic former alderman from the centrally located 19th Ward.

Making clear that Slay sees McMillan as his biggest threat, sources say his campaign staff, many of whom are also lobbyists for the city’s largest corporations, spent lots of time over the past couple of months threatening McMillan’s campaign donors, inferring that their business dealings with the city will suffer if they supported McMillan.

The pressure, those sources believe, may have left the pragmatic McMillan carefully examining his chances of winning before determining his entrance into the race. But time is running out. Filing closes on January 2, 2009. Even in a short 90-day campaign like the one Lewis Reed won over Jim Shrewsbury in March 2006, Reed announced his intentions to run on October 19, already allowing more time than a challenger to Francis Slay would have to launch a successful campaign.

In the end, in a city half-jokingly known for its two political parties — black Democrats and white Democrats — the leader of the reigning party continues to enjoy the lack of leadership in the minority party.

At some point, elections become about more than winning, but about leadership. And this city is in desperate need of some right now.