The sharp-tongued consumer advocate and Harvard Law professor is struggling to connect with working-class swing voters, many of whom seem more comfortable with Brown and his middle-of-the-road, regular-guy persona. Her fierce criticism of Wall Street has sent some Democratic Bay State financial types scurrying into Brown's camp, too.
It's the tale of two Elizabeth Warrens: the conscience of the left for many conventioneers vs. the candidate in real danger of losing the Democrats' best Senate pickup opportunity of the year. A top dog in North Carolina, an underdog in Massachusetts.
Her problems are part Brown and part her own. Warren's portrayal of the freshman senator as a covert ideologue hasn't stuck, thanks to his soft tone on cultural issues like abortion and gay rights, coupled with a well-executed, down-home ad campaign.
And her campaign message isn't resonating with a good number of Democrats. She's losing about a fifth of them to Brown, according to an Aug. 16-19 Public Policy Polling survey that had the senator up by 5 points. And more voters think she's too liberal than believe he's too conservative -- by an 11 percent margin.
"On the Democratic side, we're the victims of our own spin with Scott Brown. In 2009, we said, 'You look, he's going to be a mess, an ideologue, he's going to be stupid.' Well, he hasn't been any of those things," said Boston-based Democratic consultant Scott Ferson. "She should be 10 points up. It's a problem."
Bruce Percelay, a longtime Democratic donor and close friend of Sen. John Kerry, is making a rare trek across party lines to support Brown. Percelay plans to work for Kerry's reelection in 2014 and has given tens of thousands of dollars to Reps. Ed Markey and Mike Capuano as well as the national Democratic Party. But earlier this year Percelay gave $3,250 to Brown.
"Elizabeth Warren is not someone who I can comfortably wrap my arms around," he said. "Not everyone is willing to express it, but [Brown] is the perfect Massachusetts Republican. He's socially moderate and fiscally conservative and not a strong ideologue. People are very comfortable with that."
In an interview, he said he was unsettled by the controversy surrounding Warren's claim to Cherokee heritage and her hot rhetoric on economic disparity.
"While she's very quick to chastise the wealthy, a lot of her fundraising is coming from very wealthy people on the West Coast," he said. "There's a concern about how genuine she is. Conversely, Scott Brown is an extremely genuine person."
Asked to comment on Brown's crossover appeal, Warren spokeswoman Julie Edwards didn't back down from the Brown-as-ideologue critique, touting what she called his "support for right-wing Republicans like Sharron Angle, Christine O'Donnell, Jeff Flake and George Allen."
Still, Percelay's not alone.
Health care operator Ralph de la Torre and investment manager Jonathan Davis are two other deep-pocketed Bay State donors known for opening their wallets for Democrats. De la Torre even hosted a fundraiser for Martha Coakley's failed Senate campaign in 2009 and doled out $30,400 to the DSCC in Oct. 2010.
Both wrote checks to Brown earlier this year, with de la Torre contributing $5,000, the maximum amount allowed.
Even Democratic Boston Mayor Tom Menino, who will address the Democratic convention ahead of Warren on Wednesday night, is keeping his powder dry at this climactic moment for his party's candidate.
"That decision will be made later on," the mayor said when asked whether he'll endorse Warren, according to the Boston Herald. "Right now, it's premature."
Marisa DeFranco, a North Shore immigration lawyer who waged a primary challenge against Warren, said it was a mistake for Democrats to believe they could easily nationalize a race against such a shrewd and well-liked political personality as Brown.
"People meet him and they really like him. But you had [DSCC chairwoman] Patty Murray saying they were just going to fly a superhero in here and win. That's not how it works," said DeFranco. "There's a real disconnect between the national Democrats and people on the ground."
Brown is capitalizing on that breach, making it the defining narrative of his campaign.
He has already run three statewide ads touting endorsements from local Democratic officials. Last month, a Democratic state lawmaker accompanied Brown's wife on a series of campaign stops. Even Democrats in Warren's camp don't hesitate to muse to reporters about how likable Brown is.
Therein lies the best explanation Warren's troops have for how Brown is beating her in a notoriously blue state that Obama is projected to carry by double digits: Brown, they say, has succeeded in making the race about personality instead of substance.
Having all but ceded the fight on that front, Democrats are hoping turnout among the faithful will pull Warren over the finish line.
Warren's campaign has knocked on more than a half-million doors and will accelerate that pace after the convention, according to Philip Johnston, a former two-time state Democratic Party chairman who is hosting a $100,000 event for Warren in Charlotte this week. He said her organizational advantages will begin to bear fruit as the race comes into focus for the masses and the two share a debate stage.
"I understand some people are complaining about the campaign but ... Brown's avoiding any discussion of issues and just wants to focus on him as a human being," said Johnston. "She has a very substantive, aggressive message on economic issues. People start to pay attention after Labor Day. If she's 5 points down two weeks out, I'd start to worry. I don't think that's going to be the case."
Democrats hope to hammer home a more streamlined message coming out of the convention highlighting the implications of a Brown victory on control of the U.S. Senate.
"Just imagine if Republicans win the White House or gain control of the U.S. Senate," blared a recent Warren radio spot attempting to tie Brown to embattled Missouri Senate contender Todd Akin.
But Ferson believes the burden is on Warren to make her case case to the reflexively nonpartisan voters who will decide her fate, which likely means placing herself in some uncomfortable situations.
"In person, she's a rock star. But she's talking to people who already think she's a rock star. She should be in a room with persuadable voters, taking tough questions," he said. "She's got to preach in somebody else's church -- not to the choir in her own."
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