“In another campaign year,” The New York Times’ Maggie Haberman wrote on the day he announced his campaign, “Martin O’Malley’s résumé and good looks might be irresistible to Democratic primary voters. He is a former big-city mayor whose story of renewal in Baltimore seemed well tailored to an increasingly urban and minority party. He is a former two-term governor of Maryland—and the lead singer and guitarist in a rock ’n’ roll band. But Mr. O’Malley is running in an election cycle in which Democratic elected officials and donors have overwhelmingly focused attention on Hillary Rodham Clinton. And he already faces competition from Senator Bernie Sanders of Vermont for the support of liberals who dislike Mrs. Clinton or merely want to see her pushed further to the left.”

2020, of course, will be another campaign year. And as implausible as an O’Malley presidency looks today, the lesson of President Donald Trump is that nearly anything can happen in politics, under the right circumstances. The Democratic landscape right now suggests there will be no presumptive frontrunner in four years. A second run by O’Malley would test whether his poor showing in 2016 was due to terrible timing or weak appeal (or both). Assuming Trump’s right-wing reign of ignorance and incompetence continues, voters may be ready for another smart, liberal technocrat—a leader the Washington Monthly in 2013 called “arguably the best manager working in government.” Or maybe it’s a more familiar story: an ambitious politician with plenty to recommend him who nevertheless can’t break through on the national level.

Bill Clinton once thought O’Malley might “go all the way.” He wrote as much in 2002, the same year that Esquire called O’Malley “America’s best young mayor.” Ahead of—and even during—the 2016 campaign, progressive writers made this case for him, too. After the third primary debate, Rebecca Leber wrote in the New Republic, “O’Malley didn’t look presidential. Yet there’s good reason to take him seriously, despite his awkward night.” She noted that he was often “the first candidate to stake out detailed, even wonky, progressive positions”—on climate change, immigration reform, and healthcare—that were later adopted by Clinton and Sanders. At Vox, Matt Yglesias gushed over O’Malley’s gubernatorial record and even argued he “seems the most solid, reflecting a more consistently liberal record than Clinton’s but not veering so far left that he’s spent the bulk of his career denying that he’s a Democrat, like Sanders”:

Alas, such praise does not a candidacy make. And O’Malley’s turned out to be better in theory than in practice. He never found his footing in the (admittedly few, poorly scheduled) Democratic debates, and, like many an underdog, tried too hard to exploit trivial wedge issues with Clinton and Sanders. “May I offer a different generation’s perspective on this?” O’Malley, who is 54, once asked during a debate, drawing boos from the audience.

Tad Devine, Sanders’s senior campaign strategist, said he thinks O’Malley could fare better in 2020. “I think Governor O’Malley is a very serious, formidable candidate,” he told me. “There wasn’t a lot of room in 2016. There was going to be one candidate who was a challenger [to Clinton]. 2020 is a different kind of ball game.” Devine praised O’Malley’s ability to deliver a message, saying, “I don’t discount him in terms of raw political ability.” But Devine added that a candidate needs to fit the times, and O’Malley has to hope his executive experience and governmental know-how is in greater demand in 2020. Part of what hurt O’Malley and Clinton in 2016 was their polish—in an anti-establishment year, they looked and sounded like the establishment.