Credit Christopher Connelly/WYPR

Martin O’Malley is expected to launch his campaign for president on Federal Hill tomorrow morning. The former Maryland Governor and Baltimore Mayor has been positioning himself over the as a progressive David to challenge the Goliath that is a Hillary Clinton campaign. It’s a record some progressives in the state dispute.

Back in the early 1980s, Doug Wilson gave Martin O’Malley his first job in politics, working on Gary Hart’s campaign for president. The young Colorado senator was rising in the polls – he would later flame out in scandal. But on the verge of the primaries, Hart’s campaign was nearly out of money. Wilson says O’Malley was undeterred as he worked the field in Iowa, guitar in hand.

“Martin would busk in restaurants in order to get contributions so basically he and others could eat and work another day,” Wilson said. “But he’s also somebody who, while he was busking, was gathering names and information for the Iowa Caucuses.”

Wilson is now advising O’Malley on foreign policy matters. He says he’s been impressed over the years as he watched O’Malley build his political career with compassion and dedication to public service.

“I think he’s someone who believes in the good in people. But in addition to being idealistic, he’s pragmatic,” Wilson said. “He’s someone who’s always had a goal in mind and wanted to move forward and achieve it.”

O’Malley’s been working to frame himself to the left of Hillary Clinton as a progressive populist and as a tech-savvy fresh face. He takes selfies, everywhere. He also touts the progressive milestones he says Maryland achieved on his watch in a series of bite-sized videos on YouTube

“Equal pay for equal work. Marriage equality. The DREAM Act. Drivers licenses for new Americans,” O’Malley says in one 20-second video. “It’s all about fuller participation in the social, in the economic, and in the political life of our country.”

Washington College political scientist Melissa Deckman says carving out space on the left is a smart move because the Democratic party is having something of a progressive moment, and O’Malley can try to capture that enthusiasm. But she says O’Malley is not exactly a dyed in the wool progressive.

“There’s never been a sense that O’Malley’s been a leader out front on these issues. But rather that he’s sort of come in from behind,” when it is politically convenient, Deckman said. “I think there’s a sense on the left that he’s not as liberal as they would like, even though on paper his record is pretty progressive.”

Deckman does point out that O’Malley  did lead on some issues, like the death penalty repeal, and he kept funding for public education high throughout the Recession when other states were cutting. He did throw his weight behind a range of progressive issues that he hadn’t initially supported, which is notable in a state that is deep blue but not always progressive.

But Deckman said O’Malley has always seemed most excited about using data to make government better, and he’ll have to tie that to the progressive message he’s developing.

“I think he’s been much more about reforming government and government reform,” Deckman said. “That’s not the most sexy thing to campaign on; it doesn’t necessarily engender passionate feelings in the way that Elizabeth Waren does now or that Obama did in 2008.”

Baltimore Del. Jill Carter, a longtime O’Malley critic, says O’Malley’s record is missing key issues that are important to African Americans. The state continued to underfund historically black colleges on his watch, she says. And she points out that Baltimore was sued by the ACLU and the NAACP for O’Malley’s policing policies. “Those are not progressive things especially for African Americans,” she said.

O’Malley’s role in implementing zero tolerance policing when he was mayor, and the role those policies played in creating simmering resentment that boiled over into protests and later a riot after the death of Freddie Gray has become a widely debated issue.

O’Malley has argued that he never encouraged aggressive policing, and called for firing bad cops, but Matthew Crenson, a retired political science professor at Johns Hopkins University, says, “The recent riot in Baltimore may have done him serious injury.”

Crenson says O’Malley could find a way to use Baltimore’s recent problems to highlight the fact that he did run both a city and a state pretty successfully – something Clinton can’t lay claim to.

But O’Malley faces formidable challenges in a primary where Hillary Clinton dominates organizationally and in terms of fundraising. If O’Malley can hope to win next year, he’ll have to hope that Clinton will stumble.

“He’s waiting for something awful to happen,” Crenson said. “He’s already put together his campaign organization, established national visibility and he’ll be ready to run.”

And if that happens, Crenson says he could be perfectly positioned to take over her donors and expand his operation.

Correction: This radio and original web story misstated Gary Hart's position. He was a senator from Colorado, not the governor. We regret the error.

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