She’s black. She’s a woman. She’s a lesbian. She has a wife and family. She has the conservative butch natural cut sported by Aunties of a certain age since at least ’72. “But, what does it all mean?” both the media and the people ask. Now that the haze of this historic election win that saw two Black women running neck and neck for the first time as the leads in a mayor’s race of the third largest city in America, the question is left hanging in the air, its residue wet, clear, but still staining as narrow eyes are cast suspiciously at this new thing that was never thought to be a political possibility before has become exactly a new reality for a city whose public image hasn’t known a clean day since the era of Al Capone and whose people could barely be bothered to get out and vote beyond a mere 33 to 35% for said political miracle.

Chicago has always been a place of the complicated, enigmatic, surprising, and contrasting. There’s a reason that Chicago is the city that defeated King and sent him packing back to the South, where he inexplicably had more luck with civil rights, after he left a thin bullet-pointed plan that the city leaders thereafter used for dart board practice. There’s a reason that Chicago is also the place shaped and molded a Hawaiian-born lad and made him into someone recognizably black to black people and “post-race” to whites enough to make him the first black POTUS. There’s a reason that a city first settled and founded by a black man, Jean Baptiste Point du Sable, is also the place to found among the most deplorably racist housing tactics in America (e.g., redlining, blockbusting, sky high carceral public housing, etc.) and the most corrupt and racist police force to rival L.A.’s Ramparts in modern history. There’s a reason why the first Black lesbian mayor in Lori Lightfoot may also be the most conservative and pro-police, pro-corporate, pro-state Democratic choice the city could have made in choosing who leads her.

But, what does it mean? It doesn’t mean what it meant when Jane Byrne was elected the first woman mayor of Chicago exactly 40 years before Lightfoot. Byrne is the first mayor I remember, I was four-years-old when she was elected in 1979 and was entering third grade when she was unseated in ’83. As a child, her name seemed to be everywhere, on placards in parks, on festivals and street banners, all over in ways that suggested she was “doing things” in my child’s mind’s eye. I’d later learn she wasn’t a very good mayor in her legislative effectiveness, though she was among the first to give high profile leadership positions to blacks, passed the city’s first handgun restrictions, and was the first mayor in Chicago’s history to acknowledge the gay community without derision and moral platitudes. She, in keeping with the political era shenanigans of my upbringing, most famously stayed in the Cabrini-Green housing project for three weeks with her husband to shine a light on the crime and need there. Ultimately, the stunt and subsequent purging of 800 Cabrini-Green tenants didn’t win her the kind of fans she’d hoped for come election time, as Byrne lost in the primary to Washington.

Speaking of what it doesn’t mean. The election of Lightfoot certainly doesn’t mean the second coming of Harold Washington, the first black mayor of Chicago. Washington was the first black man to lead Chicago since the 1780s, roughly 200 years before. He unseated Jane Byrne in 1983 in the primaries and beat Republican Bernie Epton in what was the highest voter turnout in modern Chicago history, one that hasn’t been seen since, 82.07%. Washington handily won re-election in 1987 where he again beat Byrne in the primary and Republican Alderman Edward Vrdolyak in the general. Washington wouldn’t get to live to see even a year of his second term, dying in his office just months after his second election win. Despite having his policy and appointment hands repeatedly tied by the infamous Vrdolyak 29 in the City Council in what would later mirror the larger scale battles between Obama and the Republican Congress during his frustrated runs, Washington was expected to actually see through his many progressive policy promises in his second term. Of course, this is when he unexpectedly died of a reported heart attack. Accordingly, Harold Washington achieved sainthood in Chicago, following what many in the black community will go to their deathbeds calling an assassination. I certainly will.

Lightfoot may also not be the first Black queer elected mayor of Chicago. Four years after his death, rumors of Washington’s bisexuality were circulating in the Chicago black gay community I’d come “out” into in 1991, despite a wife Washington divorced in 1950 while very young and a longtime domestic partner of 20 years, Mary Ella Smith, when he died. Gay elders at the time claimed to have seen or known of him at bars and among the men their circles, though why someone like Washington would take such a public risk during his very long political life in rough and tumble Chicago politics made their claims dubious to my then young ears. These speculations were further fueled when student artist David Nelson used rumors of what Washington may have been wearing under his suit on the day he died by depicting Chicago’s first black mayor in women’s lingerie in an exhibition at the School of the Art Institute in Chicago, one selected by school leaders in advertisements of the exhibit. This prompted outrage by storming black aldermen who threatened to remove the portrait by hand, if necessary, claiming it was an effort to tarnish the reputation of a great black man and leader. The police would remove it, but not before the damage had already been done. To me the crime was less the depiction, upon review of its muddied mess, and more that it wasn’t very good art. In any case, more than any discussion of Washington’s far more concerning tax problems or blocked legislative agenda, in all the years that followed, Washington’s possible sexuality became the second most debated aspect of his life following the assumption that he’d been killed before he could substantially provide any enduring aide or relief for Chicago blacks.

Which leads us now to Lightfoot, who represents a time in which one can be out and proud, be a black woman elected with natural hair, and be publicly partnered to the same sex. But, if the last 28 years since the 1991 confirmation of Supreme Court Justice Clarence Thomas and the smattering of elected black Republican officials in the ensuing years has taught us anything, it’s that identity representation, while important to fuel aspirations of what’s possible, only goes so far. Or, as the elders used to say, all my skin folk ain’t my kinfolk.

As has been exhaustively reported, Lightfoot served as a federal prosecutor with at least one judicial reprimand and an investigation that cleared her of abusing her power as a prosecutor. As the lead of both the Police Board and Police Accountability Task Force, activists have argued there were more cases where Lightfoot defended the police or rendered unconscionably light sentences in the face of overwhelming evidence of police misconduct and brutality. Despite some high profile headscratcher cases where Lightfoot sided with the police, including in support of the murderer of Rekia Boyd, an analysis by the Chicago Tribune of trend data doesn’t bear activist accusations against Lightfoot out, with a 35% increase in officers being brought before Lightfoot’s panel being fired from duty (75% from just under 40%). However, being endorsed by most of the corporatists and status quo interests of the city suggests certain white washing alliances to black voters, so much so that the Chicago Defender, one of America’s oldest black newspapers, and the Chicago Teacher’s Union, another black Chicago powerbase, endorsed her opponent. It also doesn’t help that, during her tenure at the white-shoe law firm of Mayer Brown, Lightfoot argued the Republican side challenging Congressional redistricting against a map that would give Latinos greater representation. Indeed, throughout her career, Lightfoot seemed able to do what the status quo demanded of her with only episodic exceptions. This is what prompted the grassroots #StopLightfoot campaign against her, along with such policy responses that are anti-rent control and would expand police presence in black neighborhoods and turn the 38 closed public schools into police training facilities. Progressive Black and brown queer activists on the ground drove home the #StopLightfoot campaign while the white-identified Human Rights Campaign and several gay establishment power PACs backed Lightfoot as well. Again, Lightfoot represents my city’s ongoing study in complication and contrast.

In her first days of her administration, Lightfoot has done little to resolve the question of what does it mean to have her serve as so many “firsts?” At least not for this hometown boy. One of Lightfoot’s first public statements after her election win, of all the things worthy of her time and attention, was to describe how Chicago planned to “hold accountable” black gay actor-singer Jussie Smollett in what the Chicago police have long argued was an elaborate hoax, only to reverse herself weeks later saying the case “doesn’t rank as a matter of any importance to me.” Oy… To her credit, Lightfoot has since brought in 400 Chicago leaders of diverse backgrounds from various sectors to serve on 10 transition team committees and invited Chicagoans to share their opinions through an online form on ideas to improve the city. Unlike Washington’s embattled tenure, Lightfoot actually has a majority of largely newly elected progressive aldermen in the City Council to see through whatever progressive reform agenda for the city she puts forth. Now, what Lightfoot does with that majority power over the next four years will answer all questions once and for all. Until then, black celebrations of this historic win feel…premature, at best. At least for this hometown boy.

Cover Photo Scott Olson/Getty Images