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Election 2015 Thu Jan 08 2015

Willie Wilson's Game Plan

And then there were five: Rahm Emanuel, Bob Fioretti, Jesus "Chuy" Garcia, William "Dock" Walls, and Willie Wilson. Those are the candidates who will be on the ballot for mayor in February.

Emanuel, Fioretti, Garcia, and Walls have all been around politics, some in loftier positions, some for longer than others. Wilson, though, has no political experience. He is a 66-year-old South Side businessman.

He also just given his campaign $1,000,000 -- with more likely on the way.

A month ago, nobody was talking about Willie Wilson. Today, he is being seen as the man who could blow the whole election up.

As a reminder, municipal elections in Chicago require outright majority winners. If in the mayoral race, or in an aldermanic race, no candidate receives an outright majority of the vote on February 24, the two candidates with the highest vote totals in that race will advance to a runoff election on April 7.

Crazy things can happen in runoffs. In February 2011, 38th Ward Alderman John Rice got 48.1 percent of the vote with six candidates on the ballot. Nick Sposato finished a distant second with 24.0 percent but still qualified for the runoff. Five weeks later, Sposato pulled a huge upset, winning the runoff with 56.1 percent of the vote. Rice's 6,756 votes in February fell to 4,423 votes in the runoff.

If the winner can be denied an outright majority, then finishing second can be like making the playoffs in the NFL as a Wild Card team. Three of the last 10 Super Bowl winners didn't win their own division. Runoffs, like playoffs, can be wild and unpredictable. Incumbents want to avoid them at all costs, and for challengers, finishing second might be just as good as finishing first.

Imagine a result like this:

Rahm Emanuel 47.0 percent
Bob Fioretti 17.0 percent
Jesus "Chuy" Garcia 17.0 percent
Willie Wilson 17.0 percent
William "Dock" Walls 2.0 percent

The numbers above aren't meant to be predictions, but rather a guide to how a candidate might finish second with less than 20 percent of the vote. (There is an assumption being made that Walls, who received less than 1 percent in 2011, and who is not well-funded, will not do much better in 2015.)

It may well have been the case that even without Wilson considered, Emanuel would have slipped under 50 percent. In recent weeks, though, the funding gap between Emanuel and others has become a dominant theme of the race, making it seem increasingly likely that a runoff might be averted.

Wilson's calculus at this stage is clearly that of focusing on black wards and media buys. In both respects, he's actually directly targeting Emanuel's strengths. In 2011, Emanuel performed strongly in black wards -- thanks largely to his association with Barack Obama. Wilson is banking on cutting into that support, and in doing so, those votes will come from Emanuel, not from Garcia or Fioretti. If Wilson does try to match Emanuel in TV spend, there too he'll be reaching people the other challengers will struggle to reach. Votes he picks up from a strong TV presence are also much likelier to otherwise vote for Emanuel.

Look at the actual results from 2011:

Rahm Emanuel 55.3 percent
Gery Chico 23.9 percent
Miguel del Valle 9.3 percent
Carol Moseley Braun 9.0 percent
Patricia Van Pelt Watkins 1.6 percent
William "Dock" Walls 0.9 percent

Emanuel is more disliked now than he was then. Garcia and Fioretti should, combined, be more formidable than the Chico and del Valle combination. Braun and Watkins got their votes primarily in black wards. Wilson's money probably only needs to carry him as far as Braun got in 2011 to cement a runoff. But Wilson is looking well beyond that.

I have previously suggested that Garcia and Fioretti, at some point, have to transition away from thinking in terms of forcing a runoff, and toward thinking in terms of how to finish second. Wilson is now a factor in that consideration. Can Wilson approach 20 percent in this race? Can $3,000,000 buy enough ads to force the matter?

And what if, as commentator Russ Stewart claims, Wilson doesn't spend $3,000,000 -- instead, he spends $60,000,000?

The speculation is wild at this point, because in Wilson, we are considering a candidate who not only has no political experience, but as of the time of this writing, has no particular platform, and doesn't even have a website for his campaign. Wilson might be little more than the next Scott Lee Cohen, spending millions of his own money with little to show for it.

Dig deeper, though, and Cohen may actually be an ideal contrast. Cohen, who ran a particularly bizarre independent campaign for governor in 2010, finished with under 4 percent of the vote. But Cohen had baggage -- rare baggage. His platform consisted primarily of shouting the word "Jobs!" across the state. But before the dirty laundry was exposed, he essentially bought his way into winning the Democratic primary for Lieutenant Governor with 26.0 percent of the vote.

One man with a front row seat for Cohen's seemingly inexplicable primary victory was Rickey Hendon. Hendon, then a West Side state senator, finished third in that primary. He is now Wilson's political director. Hendon was the strategist behind kicking several other black candidates off the mayoral ballot -- he is not exactly shy about it -- and even if you abhor the tactics, the strategy makes sense.

Hendon's plan here is not difficult to understand. He is not just thinking in terms of Wilson tipping the election in favor of a runoff. He sees the numbers above and says, Wilson can finish second. And then he sees an example like the aldermanic election Sposato won in 2011 and says, if we can just get Wilson into the runoff, he might just win the whole damn thing. After all, why would people who voted for Fioretti or Garcia feel very inclined to line up and vote for Emanuel in the runoff?

At this point, the reality is that nobody really knows how to quantify Wilson. He might crash and burn before the end of January. He also might roll out brilliant television ads and truly become the talk of the town. He has no discernible platform, which would seem to be a pretty significant problem; but maybe that gives him space to conform his positions in the late throes of the campaign. And if in another month polls show him with a decent shot at finishing second and forcing a runoff in the process, who is to say he will not spend another million, or another 59 million, to try and secure that spot?

As far-fetched as this conjecture would have seemed a few weeks ago, at this point, it all has to at least be considered. For all of their merits as candidates, neither Fioretti nor Garcia have been able to capture lightning in a bottle. The media's relative willingness to cover Wilson in the last couple of weeks may indicate pessimism about any other candidate breaking out, or a lingering belief that the only way Emanuel could be challenged if someone had a couple of million dollars to spend.

There is one other possibility as well. If internal polling has convinced Emanuel's camp that the likelihood of a runoff was high anyway, the decision might have been made that it would be better to face the inexperienced Wilson in the runoff. Emanuel's camp filed an objection against Wilson's petitions and tried to get him thrown off the ballot, but before the process concluded, they withdrew the objection. Usually objections like this are seen through one way or another, if for no other reason than to make it harder for a campaign to organize, since resources would still be going into petition defense. Did Emanuel's team have a strategic change of heart? Or had Wilson and Hendon been successful in attacking Emanuel for trying to kick a black opponent off the ballot?

The question of whether it's right or wrong for a candidate like Wilson to emerge and conceptually be able to spend his way into winning an election is a vital one. If ever a major election were a textbook example of why we need public financing, this is it. It doesn't seem to matter too much how disgusted some people will be at the prospect of the election being bought, though. Just remember who our incoming governor is.

However it all plays out, Wilson is now at the table, and a likely factor down the stretch. For as much hand-wringing as there has been over who could challenge Emanuel, the idea that a key player will be a total dark horse candidate who, seven weeks out from the election, doesn't even have a campaign website, is nothing short of mind-boggling.

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William Walls / January 10, 2015 8:54 AM

This article is flawed by mindless conjecture. The 2011 Mayoral Race was just a formality after President Barack Obama endorsed Rahm Emanuel. The candidates in that race were all household names. Most people do not know CHUY Fioretti or Willie Wilson. WBEZ and other news sources acknowledge Walls is the best known Mayoral challenger. William Dock Walls received nearly 10 percent of the vote in the 2007 Mayoral race. The only reason Rahm Emanuel withdrew his objection to Willie Wilson's petitions is because Rahm's internal polls showed that in a four way race, between Rahm, Fioretti, Garcia and Walls, Walls would win outright. Blacks are 47 percent of the voting population. Walls is more popular throughout the Black community than the others. It is shortsighted to presume the Black community will not support the most qualified candidate, who just happens to be Black.

rickey hendon / January 10, 2015 9:09 AM

The Mayor filed 2 Objections to Willie Wilson. The 1st was tossed out on the 1st day because I found a major flaw. We had 14,000 verified by the Board of Elections with 10,000 more to look at when they withdrew from the last objection. We only needed 12,500

Andrew Huff / January 12, 2015 12:01 PM

For the record, Wilson now has a website:

Chris in Chicago / January 21, 2015 1:39 PM

How can we take Wilson seriously when he basically submitted a Trib questionnaire that made him seem uninformed and his campaign seem like it's not professional? And the proposals he has seem outlandish and silly, but yet we have to consider him as a real candidate that has a chance of winning. Wilson is playing the Braun role, which means he takes up political space to assist in re-electing Emanuel. If he gets into a run-off, Emanuel gets re-elected. If he doesn't go high in the election results, he deprives the two real contenders of African American votes.

Preston / January 24, 2015 10:49 PM

And since we know what a FDB MRE is, we have to assume he and Wilson have got a deal cookin.

Chris in Chicago / February 6, 2015 7:09 PM

This seems like the perfect time for Wilson to alienate White ethnic voters to assist Rahm Emanuel.

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