When I was first in the vicinity of Martin O’Malley, right after he was first elected mayor of Baltimore (in 1999), the prevailing question wasn’t if but when he’d run for president. In the New Democrat circles I ran in back then, he was a pretty hot property, interested in policy innovations on a wide range of issues that transcended his current position on the political career ladder. Even then, there was a sort of ambivalent feeling about him: he had a bit of the Bobby Kennedy aura about him–a prized quality for Democrats regardless of their ideological tendencies–but there were also questions about his depth and vision. And then there was the personal image: the wonky Irish rocker whom a lot of women found very attractive (I don’t get the sense this last credential has survived the intervening decade-and-a-half, though I could be wrong).

So now after two ostensibly successful terms as mayor and then as Governor, the appointed time for the O’Malley presidential run has arrived, and you get the sense his timing is just completely off. His earlier time served in Hillary Clinton’s orbit makes him an unlikely and very long-shot challenger to her nomination. His sudden emergence as a would-be “true progressive” champion is singularly undermined by the prior presence in the presidential field of Bernie Sanders, who has a few decades on O’Malley in rousing crowds with attacks on Wall Street and centrist “sell-outs.” And he’s definitely been wrong-footed by recent events in Baltimore, where fairly or unfairly the suspicion has been sowed that his supposedly wonky policing strategies fed a old-school habit of harassing young black men for who they were, and created a poisonous atmosphere that is now boiling over in violence and mistrust of government. It doesn’t help O’Malley that his chief accuser on this front is television writer and producer David Simon, whose depiction of Baltimore in the HBO series The Wire probably represents 99% of what political and journalistic elites in the rest of the country know about that city.

Add in the disillusionment with O’Malley among Democrats in his home state after his tax policies helped sink his designated successor in 2014, Anthony Brown, and you have a guy who at the age of 52 should probably think about deferring his presidential ambitions until 2020 or 2024. For all I know, of course, this campaign is mostly strategic, aimed at positioning O’Malley to become HRC’s running-mate or a lively prospect for the future. But right now he’s in a position where if he doesn’t get some attention by going after both Sanders and Clinton, his candidacy could sink like a stone.

At FiveThirtyEight Harry Enten put up a rather deadly post about O’Malley over the weekend that suggested the lack of support for his candidacy in Maryland made him a really unusual presidential aspirant compared to, well, just about everybody else past or present. He’ll have a brief window of interest in his candidacy before it closes for the cycle (barring some calamity hitting Clinton). If he can reverse all the indicators pointing downward in that time, then the promise a lot of people saw in him back in the day can yet be redeemed.

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Ed Kilgore is a political columnist for New York and managing editor at the Democratic Strategist website. He was a contributing writer at the Washington Monthly from January 2012 until November 2015, and was the principal contributor to the Political Animal blog.