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Former Maryland Gov. Martin O’Malley is expected to announce at the end of this month what most assumed he had been gearing up for: a challenge to former Secretary of State Hillary Clinton for the Democratic nomination for president.

His aides told reporters who had traveled along for a trip through New Hampshire on Thursday that he will likely tell donors and supporters in a conference call that he is “inclined to run,” according to The Washington Post. His announcement will likely come around May 30 in Baltimore, where he served as mayor from 1999-2007.

Presidential speculation has followed O’Malley since 2012, when it wasn’t yet clear if Clinton would seek the nomination. But despite about three years of jostling during his tenure as Maryland governor, he’ll start well behind Clinton in the race and without much name recognition.

Some of his most fervent "support" to date has come from the reliably conservative Drudge Report, whose founder, Matt Drudge, is obviously pining for a liberal challenger to Clinton as well. Upon the news on Thursday O’Malley was getting ready to announce, The Drudge Report plastered a photo of O’Malley, shirtless and in running gear, on its banner.

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He also might start behind an unexpected competitor for attention, as well — Sen. Bernie Sanders, an independent from Vermont who announced late last month that he’d seek the Democratic nomination for president. The challenge for O’Malley, political strategists and political science professors said, is to paint himself as an electable Bernie Sanders — and a more progressive Hillary Clinton.

“He has absolutely nothing to lose and everything to gain by running,” said Stella Rouse, the assistant director of the Center for American Politics and Citizenship at the University of Maryland, in an email. “He can play the contrarian to Hillary, hopefully gain some publicity and support (especially via the debates if he does well).”

But O’Malley, who always served as the presumed progressive alternative to Clinton, might need to do some work to just attain that status again. It’s been Sanders who has gained real momentum in polls since his announcement.

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Sanders jumped from 6 percent of the Democratic primary vote in April to 13 percent in May, according to surveys from Public Policy Polling. He’s also seen similar spikes in support in key states like New Hampshire, where a poll found that at least one-third of the Democratic electorate was cramming for a more progressive nominee — be it Sanders or Sen. Elizabeth Warren (D-Massachusetts). In that same poll, from the University of New Hampshire, O’Malley was still stuck at the bottom with 2 percent.

Geoffrey Skelley, the associate editor of the University of Virginia Center for Politics’ Crystal Ball, placed O’Malley behind Sanders in terms of viability in the center's newsletter on Thursday.

“Along with his policy views, Sanders’ personal characteristics may also make him a potent ‘protest’ option for liberals in the Democratic primary,” Skelley wrote. “He is assertive and knows precisely what he believes in — and is unabashed in expressing himself.”

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Rouse added: “He will have a tougher time carving out a spot to the left of Hillary Clinton now that Bernie Sanders is in the race.”

Skelley described O’Malley as someone who “fits the profile of a more serious challenger to Clinton (or did at some point).”

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The unrest in Baltimore, where protests sprang up amid the death of a 25-year-old black man in police custody, hasn’t helped. Some of the tactics O’Malley instituted as Baltimore’s mayor were criticized, and he found a mixed reception after he came back to the city from an overseas trip. The unrest rekindled a longstanding feud between O’Malley and David Simon, author and creator of The Wire. (Tommy Carcetti, the politically expeditious Baltimore mayor and Maryland governor in the show, is loosely based on O’Malley, Simon has said.)

“O’Malley has a very steep hill to climb. First, he left the Maryland governorship, pretty much with his tail between his legs. His approval numbers were underwater at 41 percent,” Rouse said. “Second, the recent Baltimore riots did not help O’Malley. While he thought he could garner some positive publicity by ‘returning home,’ his policies of tough policing when he was Mayor of Baltimore came under scrutiny.”

O’Malley has, however, become much more willing to challenge Clinton more directly recently. He has come out against a trade deal that most liberal Democrats oppose, as well as drawn a contrast and implied that she has hedged on her support for the deal in light of political expediency. Clinton helped craft the early stages of the deal as secretary of state, but has said more recently that she needs to see the final parameters before announcing her position.

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Many progressives think he simply needs to get out his message to a wider audience. On the stump, he often talks about his progressive record as governor. He did the tax hikes on the wealthy. He did the minimum-wage hike. The death penalty is gone in Maryland. Gay couples can marry. Undocumented immigrants can qualify for in-state tuition. Health-care reform in Maryland has real legs and is in the midst of a revolution.

But does that message have a place anymore?

Said Rouse: “I think his message will easily get drowned out and he will have a tough time getting that message out there and gaining any campaign traction.”

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Brett LoGiurato is the senior national political correspondent at Fusion, where he covers all things 2016. He'll give you everything you need to know about politics, with a healthy side of puns.