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12:15 a.m., Nov. 23: Mayor-for-Life Marion Barry’s heart, which survived segregation, federal prosecutors, and spending every second beating along with one of the most notorious partyhounds of the 1980s, gives out.

1:46 a.m.: Barry is pronounced dead at United Medical Center.

5:15 a.m.: With Barry gone barely five hours, a Ward 8 striver texts LL about his plan to seize his D.C. Council seat.

If it was some other incumbent on the slab and the mayor-for-life had been a little more tech-savvy, it could have been Barry behind that text. The icon’s death at 78 years old has left his city sifting through contradictions, as if just thinking about him enough after the fact could reveal whoever he really was. But one thing about Barry won’t need explaining: He was always looking for his next opportunity.

He was a man who loved the city’s disadvantaged, and one who presided over a descent into murder and drugs in the poorest wards. He outmaneuvered his opponents in all but one race, only to commit idiotic unforced errors in office. He was the most lovable figure in District politics (a petition to rename H Street and Benning Road NE after him has more than 500 signatures as LL writes this barely 12 hours after Barry’s passing), despite also being one of its all-time dirtballs. He was an inspiring person to encounter, whose record in office was often anything but.

Most of that Barry pondering will focus on his first three terms as mayor, plus the miracle of his re-election (if not his ensuing administration) despite the crack cocaine conviction. There’s the great stuff about Barry: the summer jobs program, the still in-progress attempt to unshackle the District from white overlords imposed from out-of-town. And there’s the terrible: Barry’s willingness to shrug it off or snort it up as his pals pillaged the District’s treasury.

But for true connoisseurs of Barryismo, LL suggests checking out some less glamorous years: 2005 to 2014, Barry’s final stretch on the Council. Away from the national attention, the Virgin Islands junkets, and the women, Barry could dedicate himself to his dearest cause of all: Marion Barry.

Leaving office in 1999 after flirting unsuccessfully with a fifth mayoral bid, Barry faced a challenge few iconic big-city mayors have known: accepting a demotion for a chance at staying in the public eye. New York’s Ed Koch retired to a life of semi-professional movie reviewing, while Rudy Giuliani tried to be president before settling for being a neocon gadfly and public safety troll. Richard J. Daley never had a chance to find out what life after the tsardom of Chicago would be like, opting to keel over instead.

But the District’s colonial status meant that Barry could never take the next step for a politician of his popularity and run for governor or senator, an injustice that delighted the many congressional foes he managed to outlast. Instead, after a stint at a bank, he returned to the position that brought him a final mayoral term: the Ward 8 Council seat.

It’s hard to be wowed by what he managed to accomplish as a legislator. Barry became one of the Council’s most reliable voices for the poor, both in impoverished Ward 8 and elsewhere, without passing many actual laws to help them. His final years were marked by a persistent refusal to abide by the time limits on Council speeches—sometimes to speak on his constituents’ behalf, but mostly for his own self-aggrandizement.

His most memorable appearances while on the Council produced more pathos than results. In 2010, there’s Barry begging old pal Vince Gray, then the Council chairman, not to censure him for his role in an elaborate earmark-funneling scheme. In 2013, it was longtime Barry fixer Anita Bonds, now a councilmember herself, who voted to censure her old patron for taking illicit cash gifts. Each of these lapses hurt Barry’s constituents, too, costing him control over a Council committee (and the ability to steer city dollars their way that comes along with it).

High off his latest win in 2012, Barry promised to clean up his ward’s Asian-American-owned “dirty shops.” Attempting to flail his way to an apology, Barry gaffed again by bringing up “Polacks” as an example of another discriminated minority.

Despite all that—and the tax woes, and the unpaid parking tickets—Barry remained beloved. And if you didn’t believe him, until this Sunday, you could’ve just asked him. Standing outside a polling place with Muriel Bowser on Election Day, Barry lamented the low level of interest in the race. He did have one candidate in mind who always got people excited, though.

“If I were running, it’d be a different story,” Barry said. “It’d be nothing but excitement in this campaign.”

He was right. Anyone hoping to talk to Barry would have to dodge a constant stream of well-wishers with smartphones; he may go down as the District’s most selfied personality. (Barry’s charisma didn’t always work. In July, a screening of a Barry-produced documentary on his ward had to be postponed for months after lukewarm interest, according to emails obtained by LL through a Freedom of Information Act request.)

Barry’s most extensive legacy work came in the form of Mayor for Life, his book-length attempt to explain himself. In the memoir, Barry and his co-author skate over the more awkward portions of his life: His first wife is introduced and dispensed with in a single sentence. One embarrassing section, on a relationship with a woman to whom he steered earmarks, was prepared in a late draft but deleted from the final copy.

As always, Barry delighted in getting out of a jam. Last month, Barry teased LL that a story about his use of Council staff to work on his memoir didn’t get much attention aside from the Washington Post editorial board. Barry, used to more than two decades of Post attacks, said that didn’t count. For the people who loved him, it didn’t either.

As Barry burnished his mayoral bona fides, though, whatever history he would leave behind as a councilmember became slighter. More than once on the dais, he demonstrated a complete disconnect between what a piece of legislation would do and what he thought it would do. At a dinner promoting his book, Barry fiercely denounced a nonexistent “yogurt tax.” No one there, LL included, pointed out that he had actually been asked about a so-called yoga tax.

Even without his frequent hospital visits, Barry’s health had obviously been declining. When Barry endorsed Gray in the Democratic primary, Gray’s campaign manager warned photographers not to shoot Barry as he limped to the stage. At an October get-out-the-vote rally for Bowser, Barry struggled to leave the platform with the other worthies, leaving him awkwardly stuck in front of the band as they started their set.

Not that the band minded. Even in his dwindling years, Barry was the best frontman the District could ask for. Barry clearly felt the same way, which explains why he inevitably belted out “Call It Stormy Monday” whenever he was within 10 feet of a microphone.

Seeing Barry on the Council, it was easy to feel that he was diminishing his mayoral legacy. Maybe he would’ve been better off staying out of office after leaving the mayoralty in 1999, as many supporters and enemies hoped he would.

But if he could have quit, he wouldn’t have been Marion Barry.

Photo by Darrow Montgomery

Got a tip for LL? Send suggestions to lips@washingtoncitypaper.com. Or call (202) 650-6925.