One spot featured Quinn at a Ford plant talking about “the very best way to help people”—a job. Another spot had Quinn direct-to-camera saying, “You know me. I’ve been a fighter all my life. I fought the big utilities and saved consumers billions.” Yet another focused on veterans and education. This was the contrast we sought: “You know me,” versus, “Who is this guy?”

Bill Brady was defined, by his campaign, as a two-dimensional candidate—a relatively unknown, flat figure. They allowed us to fill in the third dimension: emotional depth.  With Quinn, we sought to appeal to the heads and hearts of voters to establish a stronger connection. It worked.

When asked by his hometown newspaper why he lost, Brady answered, “Evidently, we didn’t earn enough trust yet.” That was the focus of our paid advertising. 

It’s All About the Timing

To win an “impossible” campaign, timing is everything and given where Quinn stood in the polls over the summer, we knew we needed to design momentum into our campaign strategy on multiple levels. Peaking too soon would be fatal. Campaigns that depend solely on a sudden surge of emotional momentum, too early and without strongly anchoring their lines, risk being blown off the mountain by the first strong gust of negative that comes their way. Emotional surges are central to every upset—but the timing must be perfect and it needs to happen as late as possible.

With that in mind, the first thing we did was to hold off spending money as much as possible throughout the summer in order to maximize our impact on TV in the last eight weeks. Insiders and pundits had already written off the campaign as a sure loser, but we had a rule, and we stuck to it: If Brady went up on Chicago TV in a serious way we would match him, otherwise we would hold our money until voters really started paying attention.

Like the classic fable of “The Tortoise and the Hare,” Brady and his advisers thought they had it won. Brady didn’t go up with a serious ad buy in the Chicago media market and we held fast. The strategy paid off big by allowing us to put more money on the airwaves when it mattered most—the final eight weeks of the race.

When it came to the spots we did put on the air, we took a measured approach, carefully crafting the rollout of each TV ad. We did not lead our media campaign with our strongest negative against Brady—the fact that our millionaire opponent didn’t have to pay any federal income taxes for two straight years. Nor did we combine all of our most potent attacks into a single ad, as is typical.  

Instead, we wanted to build momentum against our opponent brick by brick, issue by issue. We knew that if we first set up Brady as the Porsche-driving millionaire who wanted to lower the minimum wage, it would make our spot on Brady not paying any federal income taxes for two straight years even more powerful. After we ran the spot on Brady’s taxes, we continued to hammer home the point with voters by beginning subsequent spots with, “Remember politician Bill Brady? The millionaire who somehow didn’t pay any federal income taxes? Now we find out…”

Each spot ended with a question: “Who is this guy?” The goal was to have voters asking themselves that question. When we presented new facts on Brady, they would stick because it would be fitting a certain pattern of behavior. “Who is this guy?” implicitly says:  “Who would do something like that? I don’t know this guy. He’s a stranger to me, and now I’m finding out things that he’s keeping from me?”

Finally, we knew from our research we could only raise Quinn’s favorable ratings a finite amount given the beating he weathered in his primary fight. If we raised his favorable ratings too early with positive media, we’d be stuck, but if we waited until the last 15 days it would allow us real movement against Brady. The goal was to make sure Brady was at the same level as Quinn with unfavorable ratings and then with a last minute injection of positive media, we would play our trump card—highlighting Quinn’s character and values and shoot above Brady for real momentum on Election Day.

The strategy paid off and that’s exactly what happened.