Maybe one day, several years from now, Adrian Fenty will look back at this election, chuckle to himself, and print up a T-shirt that says “I spent $5 million on my re-election bid, and all I got was this lousy T-shirt.”

Because when the polls close Sept. 14, barring some unforeseen event that reverses Vincent Gray’s huge lead in opinion polls (including Washington City Paper’s—page 20), Fenty won’t have much else to show for all the money, energy, and time that went into his campaign.

There will soon be great hand-wringing and op/ed-ifiying about what a Fenty loss means in terms of education reform, young black politicians, and the District’s path toward gentrification. But the bottom line is this: Fenty could have—should have—won this one. He just had way too much faith in his own political skills, and ran a lousy race.

For now, Green Team-ers aren’t willing to go on the record with discontent, anger, or finger-pointing over missed opportunities. Expect that to change Sept. 15. But until then, here are some of the obvious ways Fenty went wrong:

Don’t fear the pollster. Fenty doesn’t trust polls. He didn’t use them in 2006, and his campaign spokesman says he hasn’t used them in this race. Instead, Fenty says he prefers to get his sense of the city’s mood directly from its residents. That’s why he says he didn’t know how deep his troubles ran until he started canvassing in earnest this spring—after Gray entered the race.

“That’s when I really started to get the feedback from people, and then, at that point, you learn it, and then you talk about it and tell people what you’re going to do,” Fenty told The Washington Post.

Team Fenty tries to spin this peculiar habit as a “man of the people” shtick that shows the mayor puts doing what’s right over doing what’s popular. But it’s unwise to choose not to glance at warning gauges that could show you heading over a cliff, especially since Fenty had plenty of money to pay for a survey or two.

“That’s like being a fireman and not trusting water,” says Chuck Thies, a political consultant who supports Gray. “You ignore polls at your own peril.”

If Fenty did pay attention to polls, he would have seen plenty of signs of trouble. As early as August 2009, surveys illustrated the paradox that’s been the overarching theme this year: voters are pleased with the city’s progress, but unhappy with their mayor.

When the most recent Post poll came out Aug. 29 showing Gray with a 17-point lead among likely voters, Fenty’s wife, Michelle Cross Fenty, made a rare public appearance to defend her husband’s personality. She said she was “shocked” by the poll, and that it confirmed their worst fears. The real shock? That Fenty wasn’t shocked by a poll until two weeks before the election.

If you’re going to say you’re sorry, say it early, say it often, and say it like you mean it. Things started off great for Fenty. He raised more than $2 million in three months, over half of it in a single seven-figure week in December 2008.

A spiffy video—complete with soundtrack and fancy editing—of one of those events, Fenty’s 38th birthday party at developer Chris Donatelli’s house, sits on YouTube now as an artifact, its cocky self-assurance about the outcome of the race laughable in retrospect.

“I am so excited about the next four years, I’m so excited to keep the type of reforms going that we’ve done in the government and in education, and I’m so excited that we are still on this great path to quickly move us to being the world class city that all of us know that we can be,” Fenty told supporters then.

Hizzoner officially kicked off his campaign in April with a defiant, unapologetic tone that tried to spin his style problems into positives. “We did it because it was the right thing to do,” was Fenty’s mantra, whenever he was challenged on the way he went about things.

What’s now clear is that Fenty’s initial approach didn’t work. Why? He was a) telling people what they already knew—the city is improving, but your mayor is a jerk, and b) underplaying how strongly people felt he was a jerk.

Fenty finally wised up and started trying to apologize to people in August, but the contrition tour has seemed insincere and desperate. Several people inside and outside the campaign think Fenty’s apology tour is too little, too late, and he should have started apologizing before Gray even entered the race—which might have kept him out.

Rely on pros, not your shady buddies who’ve done really well since you’ve come to power. Fenty stormed the castle in 2006 with a band of bright and loyal young Turks who ran an inspired, populist campaign. Former campaign staffers still have stars in their eyes when reminiscing about their remarkable run.

“I really felt like that morning that we could fix everything if we worked hard enough and smart enough,” says former aide William Singer of the morning after Fenty won the primary.

But the 2006 band broke up a long time ago. Still left? John Falcicchio, who has done a fantastic job raising money for Fenty, and Sinclair Skinner, one of Fenty’s best friends—who is under investigation for allegedly ripping off taxpayers with his pal in power.

Skinner’s exact role in the campaign isn’t clear. He’s not listed on financial disclosure forms as a paid consultant, but several sources say he’s played a leading role in directing Fenty’s field operation. Campaign spokesman Sean Madigan says Skinner is a “volunteer.”

Then there’s the guy who’s somehow made himself Fenty’s unofficial spokesman: Ron Moten, an ex-con and co-founder of Peaceoholics, the group that’s received millions in public funds under the Fenty administration with little oversight.

Fenty seems to have ceded the campaign’s efforts to reach out to black voters to Moten, who organized go-go concerts, released pro-Fenty songs and a music video, and published a magazine that attacks Gray and offers 13 reasons why African Americans should support Fenty. At times, Fenty just sits in the background—literally. When Moten called a news conference to accuse Gray of trying to get go-go musician and Fenty supporter Anwan “Big G” Glover yanked from his WKYS-FM radio show, Hizzoner showed up midway through, standing off to the side staring at the back of Moten’s head until reporters asked him to speak.

Madigan says Moten is a volunteer, but the Post has called him a chief strategist. “How do you let that happen?” asked a Gray staffer of Moten’s outsized role in the campaign.

Why Fenty chose to keep political liabilities like Moten and Skinner so close may be a mystery, but it shows the absence of a seasoned pro in his campaign. Hizzoner’s one-time political guru Tom Lindenfeld—who helped elect Anthony Williams, Fenty, and some guy named Barack Obama in 2008—has been virtually invisible.

Madigan tries to spin Fenty’s refusal to hire “a bunch of hired guns” to run his campaign as a virtue. “He feels very invested in his campaign, and it’s a very personal operation for him,” he says.

But when Fenty makes the case for his re-election, he says he’s a good manager specifically because he hires good people (ahem, Michelle Rhee) and lets them do their job. Which is a decent point. If he’d followed the same strategy in his campaign, LL might not be writing pre-election post-mortems.

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