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When trying to understand what happened in this mayoral race, remember that Carl DeMaio really wanted to run against Bob Filner.

DeMaio and the Republican Party set out in March — well before the June primary election — to frame the race as a contest between DeMaio, the taxpayer representative, versus “the choice of government employee labor unions Rep. Bob Filner.”

They did this even though there were two prominent Republicans still in the race.

DeMaio’s team admitted that facing Filner in the general election was much more attractive than facing Assemblyman Nathan Fletcher. So they blitzed Fletcher with a ruthless and effective string of attacks.

Fletcher’s momentum plateaued and he failed to advance out of the primary. Filner survived in second place.

Voters have now elected Filner mayor.

Working to ensure a showdown with Filner was only one of the ways DeMaio tried to win. He made so many big moves that now prove that no move was big enough to lift him to a win.

He had made the meteoric rise in San Diego politics based on the promise that San Diego could become what columnist Chris Reed called the “Ground Zero for government experimentation — of a sort that many will call radical but that libertarians will call long-overdue.”

DeMaio’s antipathy toward organized labor was so strong, it created a backlash. And Tuesday, that opposition joined forces with a wave of more liberal voters that sunk him.

We knew who DeMaio was in 2008. He was the same, if not more brash in 2010. That person, it appears, could not have been elected mayor in 2012. No matter what he did.

I’m not saying people should have known that. I certainly didn’t know that.

The fact is that 2010 DeMaio could not have hoped for more things to go his way as he marched toward his goal of becoming mayor. He helped crush a sales tax hike championed by the mayor. He managed to raise more than $1 million to pass a pension reform initiative that garnered national attention. He positioned himself as the Republican standard-bearer and the party reciprocated with an early endorsement.

Then he got what he wanted when he pushed Fletcher out of the race.

At the same time, Filner did everything possible to hurt his own chances. The congressman gave his allies heartburn and made far more enemies than he needed to. Debate after debate, he seemed to get worse and worse.

DeMaio surged. A SurveyUSA/KGTV poll kept showing a simple trend: A once solid Filner lead was eroding.

While Filner alienated potential friends, DeMaio recruited former nemeses, and his coalition expanded with Democrats. He began to almost disavow his party, calling the words “Democrat” and “Republican” hurtful labels.

DeMaio knew he’d face a much more liberal electorate in November. So he stepped onto uncomfortable ground. He refused to say he supported Mitt Romney for president. He wouldn’t even come out against Proposition Z, a large tax increase that would have been a no-brainer to the DeMaio of only a few months ago.

It seemed to work, and Filner’s unforced errors intensified.

But that’s where it ended. DeMaio couldn’t get anything more. All that was left he could have hoped for was to neutralize, somehow, the movement labor unions had put together to take him down.

It didn’t happen.

And that’s what kept Filner on top. It wasn’t Filner’s performance, it was the people he empowered that got the job done. The ads his team and supporters within labor put together were superior to DeMaio’s. They were concise and effective and they had only one goal: to define DeMaio as a tea party Republican.

Labor union leaders had been working on the plan for years. From the moment it became obvious that DeMaio would run for mayor, they worked to define him, to dog him and to demonize his brand of innovative but divisive conservatism.

He relished the attention in front of a more conservative primary electorate, but underestimated its power in the general election.

Ultimately the same thing that gave DeMaio the prominence to run for mayor was what crippled him: his ability to define the city as us, taxpayers, versus them, the “government unions.”

His leadership in conservative circles inspired a legion of young idealists wooed by the promise of what the free market can achieve for local government. Even when he diluted his philosophy to fit the old San Diego establishment and its goals, they fought for him.

They didn’t know how to appeal to liberals, though.

If Republicans knew their candidate would need to distance himself so far from their brand, they’d never have chosen DeMaio.

DeMaio had been working his whole life on making a case for the Republican Party. It was simple: Government could potentially get a lot more done if it a) accepted that it could not do some public service as efficiently as private businesses and b) it compensated its employees based on results, not seniority and not with across-the-board benefits.

He learned a lot in these last few months and said something interesting after the election.

“The reform agenda must evolve. We must move beyond balance sheets and finances and we must look at every service of our city government and we must commit to making City Hall work for every single neighborhood,” he said.

This was always a problem for DeMaio. For many years, it was just balance sheets and finances. He knew why, because that is what ultimately matters for any organization’s ability to deliver on its mission.

The balance sheet message resonated with suburban conservative voters. But when it came time to make the case to others, the movement against him was too strong. He got better at selling this new compassionate libertarianism.

But they weren’t buying fast enough.

I’m Scott Lewis, the CEO of Voice of San Diego. Please contact me if you’d like at scott.lewis@voiceofsandiego.org or 619.325.0527 and follow me on Twitter (it’s a blast!):

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Disclosure: Voice of San Diego members and supporters may be mentioned or have a stake in the stories we cover. For a complete list of our contributors, click here.

Scott Lewis

Scott Lewis oversees Voice of San Diego’s operations, website and daily functions as Editor in Chief. He also writes about local politics, where he frequently...

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