More than a decade ago, Bill Clinton threw his arm around the handsome, brash leader of Baltimore who had just been named by a national magazine as the country's "best young mayor."
"Congratulations to Mayor O'Malley on being the Esquire magazine cover boy," Clinton teased as a dozen cameras captured the moment unfolding at New York University. "I hope it's just the beginning of greater things to come."
Martin O'Malley, the former mayor and two-term governor of Maryland, is set to take a step toward realizing that future on Saturday by announcing a presidential campaign some believe has been in the back of his mind — if not in the works — almost since the encounter with Clinton.
The 52-year-old Homeland resident, whose governorship ended in January, will announce his decision in Federal Hill Park, with the city he once led as his backdrop. Hours later, he will fly out of Maryland for a weekend of events in Iowa and New Hampshire.
O'Malley faces significantly long odds as he takes on former Secretary of State Hillary Clinton for the nomination. He barely registers in polls — President Barack Obama recently joked about O'Malley's lack of name recognition — he has limited support, even in Maryland, and he has faced a number of significant setbacks in recent months.
But O'Malley's supporters insist many of those problems will be mitigated once people take a closer look at the man who ushered in a tech-focused administration at City Hall and achieved a heady list of liberal accomplishments in Annapolis, including the legalization of same-sex marriage and an increase in the state's minimum wage.
Looked at one way, O'Malley has nowhere to go but up.
"He's an underdog," acknowledged Maryland Attorney General Brian E. Frosh, one of only a handful of elected Democrats in Maryland who are supporting the former governor. "But when voters hear what he has to say, I think they'll find him extremely appealing."
Maryland has never produced a president and has rarely even offered serious candidates. Alan Keyes, who lived in Montgomery County, ran for the GOP nomination in 1996, 2000 and 2008. The last Maryland governor to seek the presidency was Albert C. Ritchie, who lost the Democratic nomination to Franklin D. Roosevelt in 1932.
O'Malley, who was first elected to a seat on the Baltimore City Council in 1991, has attempted to position himself to the left of Hillary Clinton on trade, immigration and Wall Street regulations. That space has become increasingly crowded, though, as Clinton herself has tacked to the left and candidate Bernie Sanders, a Vermont senator, has emerged as a voice for progressives.
The former governor can count tougher gun laws, a repeal of the state's death penalty and several policies to help immigrants in the country without legal documentation among his accomplishments. Critics focus instead on higher state taxes and, more recently, a tough-on-crime policing strategy during his tenure at City Hall that some believe harmed relations between the police and the community.
At least one group, citing the death in April of Freddie Gray from an injury sustained while in police custody, is planning to protest O'Malley's announcement on Saturday.
The Republican National Committee sent out a "meet Martin O'Malley" slide show on Friday that described him as "too extreme for his home state," and noted that his lieutenant governor, Anthony G. Brown, was defeated by Republican Larry Hogan in last year's gubernatorial election.
Most of the state's elected leaders — and its congressional delegation, in particular — have endorsed Clinton. Sen. Barbara A. Mikulski, the dean of the delegation and a longtime supporter of Clinton, was among the first to publicly announce her endorsement of the former senator from New York.
Mikulski has also had a strong relationship with O'Malley. He worked on her first Senate campaign in 1986. She has employed his 87-year-old mother in her Capitol Hill office for decades.
"Governor Martin O'Malley should follow his dreams," Mikulski said in a statement. "I look forward to the ideas and energy Governor O'Malley brings to the conversation over the coming year."
Though many state politicians will avoid Federal Hill, some will be there to stand with O'Malley. Prince George's County Executive Rushern L. Baker III recalled O'Malley's early work in attempting to address violent crime and the drug trade in Baltimore. He also noted the relationship he had with O'Malley as governor.
"I came to him on every critical issue facing our county, and when I said, 'I need your help,' he was there to help," Baker said. "I've seen his commitment to making life better for everyone."
Details of the event have slowly leaked from O'Malley's political operation in recent days. The former governor, who has long fronted an Irish rock band called O'Malley's March, will bring in the Baltimore-based Kelly Bell Band to play for supporters. On Friday he posted a video of himself playing the opening notes from the official presidential anthem, "Hail to the Chief."
Aides also announced O'Malley had hired Obama's director of Hispanic media, Gabriela Domenzain, to serve as the campaign's director of public engagement.
Democratic political consultant Steve McMahon prefaced his thoughts on O'Malley by noting that Clinton appears to have the nomination locked up. Asked whether there was any potential path for O'Malley, McMahon pointed to a history of races in which the underdog has been given an opportunity.
"There's generally been a moment during which the presumed prohibitive front-runner looks like they might be in for a race," he said. "Almost invariably the insurgent gets crushed, either quickly or eventually, but that doesn't mean that the moment didn't occur — that it isn't possible."
Baltimore Sun researcher Paul McCardell contributed to this article.
If you go
O'Malley's announcement at 10 a.m. in Federal Hill Park is open to the public. Gates open at 8 a.m., and a shuttle will be available from a parking lot at 1215 E. Fort Ave. Curb lane closures will be in effect from 7 a.m. to 1 p.m. on eastbound portions of Key Highway and Warren Avenue near the park. Parking restrictions will be in place on Covington Street from Key Highway to Grindall Street, according to the city.