With Election Day rapidly approaching, we’re publishing a Reader’s Guide on each of the four major candidates to review just about everything you need to know before stepping into the polling booth.

Let’s get started with Republican City Councilman Carl DeMaio.

A Video Introduction

View more videos at: http://nbcsandiego.com.

The Pitch to Voters

DeMaio’s fought pensions, tax increases and unions, and fought for outsourcing for a decade. You know where he stands and he won’t compromise on his core principles.

Three Big Issues

More than any other candidate, DeMaio not only makes clear what issues he cares about, but also what he’d do to address them. His three issues, which he’s fond of repeating on the campaign trail, are pensions, potholes and prosperity.

• Pensions.

DeMaio was the driving force behind Proposition B, the pension initiative also on the June ballot, which will give most new city workers 401(k)s instead of guaranteed pensions and attempt to freeze current employees’ pensionable pay for five years. He’s by far the most knowledgeable on the issue.

DeMaio also wants to eliminate completely the Deferred Retirement Option Plan, which allows employees to retire but keep working and bank their pension payments.

• Potholes.

The councilman again distinguishes himself by having the most comprehensive plan to address the city’s decaying street system. Unlike the rest of the candidates, he’s identified a way to pay for road repairs by sequestering future tax revenues. He recently unveiled a proposed November ballot measure that would enact his plan and pivot his general election campaign from pensions to potholes.

• Prosperity.

DeMaio’s economic development plan relies on slashing government fees and regulations and making it easier for the city to outsource its work. He’s specific in what he wants to cut from solar permitting fees to some parking regulations.

The bottom line is, that of the four major candidates, DeMaio gives you the strongest indication of what he’d actually do while he’s in office. The question, then, is if that’s the direction you want for City Hall.

His Background

DeMaio’s background is filled with intrigue.

He made the millions that have fueled his San Diego political career in Washington D.C. running conferences and training on a federal law he helped make relevant. In Washington, he followed the same playbook for success as he has in San Diego: He appeared out of nowhere, seized an issue headed for prominence, worked relentlessly and took credit even when it wasn’t quite due. We described his shifting roles this way in a story about how he made his money:

It’s never been clear, either in Washington or San Diego, if DeMaio is working on behalf of himself or the ideas he’s promoting. He has crossed the boundaries between partisan and nonpartisan, business and politics, and innovator and imitator so often that it’s difficult to understand what’s motivating him on any issue.

In the campaign’s past few months, DeMaio has started to talk publicly about the challenges he faced growing up. That’s a marked change from before. We summarized his history in a piece about his difficult childhood and personal blind spot:

Talking about his background makes him uncomfortable. The facts of DeMaio’s life, though, are both tragic and fascinating. He was essentially orphaned as a teenager. He’s a drown-government-in-the-bathtub Republican leading a push against the party’s more moderate side. He’s in a committed relationship with the publisher of a prominent gay newspaper.

Where DeMaio’s Weak

No local politician inspires more emotion than DeMaio. This cuts both ways. He has rock-ribbed supporters, but also makes lasting enemies.

By themselves, DeMaio’s views make him the most hardline of any major candidate and might have been enough to attract the kind of Anybody-But-DeMaio campaign that the city’s labor unions have financed. After all, he’s said he wants to make San Diego, “The Wisconsin of the West,” a state at the forefront of the ideological battle between conservatives and liberals over the role of public sector unions.

But it’s more than his ideas. His confrontational style, propensity to overreach and an unwillingness to admit when he’s wrong has made it difficult to understand how he’d work with the City Council and various interest groups to implement the massive changes he wants.

Biggest Hit

DeMaio is the best in San Diego at controlling the daily and long-term political narrative. He’s been able to make the June campaign about pension reform, the issue where he’s shown the most leadership and forcefulness. On a regular basis, DeMaio makes you believe that City Hall is broken and he’s the one with the most ideas to fix it. DeMaio has led the primary polls since the race’s first day.

Biggest Flop

It’s clear that DeMaio believes Assemblyman Nathan Fletcher is his largest threat. So he’s tried to attack him. But on two occasions, DeMaio’s failed. More than anything else during the campaign, these failures revealed the chinks in DeMaio’s armor.

DeMaio used the campaign’s first live, televised debate as a platform to ask Fletcher if he was under an ethics investigation, a classic “gotcha” move. But it backfired when it was revealed that the Ethics Commission dismissed a DeMaio-supported complaint against Fletcher a day earlier without an investigation.

DeMaio also tried to tie Fletcher to past leaders who were key figures in the city’s pension woes. He made a show of asking Fletcher to return a donation from former City Manager Jack McGrory, who engineered the first pension underfunding in the mid-1990s. Fletcher and McGrory responded by revealing that DeMaio had solicited McGrory for a donation through email. In a buck-doesn’t-stop-here moment, DeMaio blamed an intern for the mix-up.

Top Endorsements and a Snapshot of DeMaio’s Views

DeMaio’s key supporters: The Republican Party of San Diego County, U-T San Diego, former Mayor Roger Hedgecock, Howard Jarvis Taxpayers Association.

You can quickly understand DeMaio’s positions on major city issues compared to his opponents through our mayoral scorecard.

How He Wins

It’s hard to find anyone at this point who believes that DeMaio won’t be one of the top two finishers in the primary and move on to November’s general election. His supporters are too solid, his campaign infrastructure is too strong and his political narrative is too entrenched for him to fail.

DeMaio’s problem, then, is November where his more radical stances will see a less friendly electorate. DeMaio’s identified his biggest November problem as Fletcher. If DeMaio’s efforts help keep the assemblyman out of the runoff then DeMaio will have won twice on primary day.

Liam Dillon is a news reporter for Voice of San Diego. He covers San Diego City Hall, the 2012 mayor’s race and big building projects. What should he write about next?

Please contact him directly at liam.dillon@voiceofsandiego.org or 619.550.5663.

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Liam Dillon

Liam Dillon was formerly a senior reporter and assistant editor for Voice of San Diego. He led VOSD’s investigations and wrote about how regular people...

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