Ask most anyone in Ward 7 their opinion of Councilmember Vince Gray and they’ll start by describing his titanic stature in D.C. politics, his long list of achievements stretching back decades, and his fine representation of the ward that has persisted despite his advanced age and health challenges. Generally, all that praise is followed by one very large “but.”

Gray is up for reelection in 2024, and pretty much no one is excited to see him run again. The former mayor appears frail and sometimes confused in his increasingly rare public appearances, he can only attend Council meetings virtually (and he’s missed several key votes due to medical appointments), and he isn’t as responsive to his constituents as he once was. Gray turns 81 later this year, and he’d be 86 if he manages to win and finish another term as councilmember. Many Ward 7 politicos would rather see Gray step aside gracefully, and those who spoke with Loose Lips expect he’ll ultimately do so.

There’s no small amount of self-interest behind those prognostications, of course. The ward hasn’t seen an open seat race since the 2007 special election to replace Gray after his ascension to Council chair, and there are plenty of politicians itching to take a crack at the race. LL hears that an open seat race could easily attract a dozen or more candidates of varying levels of skill and experience. Ebbon Allen, a former advisory neighborhood commissioner and teacher, has already filed to run, and others could jump in the race in the coming months. But many are waiting to see what Gray will decide first.

“It feels like the writing’s on the wall,” says Patricia Stamper, a Deanwood activist who ran briefly for the ward’s State Board of Education seat in 2020. “It’s kind of like watching Muhammad Ali in one of his last matches.”

There are still 10 months before the June 2024 primary, but LL hears that plenty of candidates are already testing the waters for potential runs. Ward 7 politicos have frequently mentioned Advisory Neighborhood Commissioner Kelvin Brown and attorney Veda Rasheed as potential candidates after they ran against Gray in 2020, and both tell LL that they’re considering bids this time around too. Whispers abound about two other fresh faces as well: Ward 7 Democrats chair Wendell Felder and current SBOE Rep. Eboni-Rose Thompson.

And then there’s the chatter about the ward’s old guard: former Councilmember Yvette Alexander, whom Gray ousted in 2016, and Villareal “VJ” Johnson, a former ANC commissioner and president of the Hillcrest Community Civic Association. There’s even the chance that Kwame “Fully Loaded” Brown decides to mount the political comeback he’s occasionally hinted at since his 2012 resignation as Council chair, though opinions vary about just how seriously Brown would consider a run.

LL has also heard occasional rumors about ANC Tyrell Holcomb or former at-large candidate Karim Marshall jumping in, too, but most politicos don’t consider them particularly serious contenders. (Marshall has repeatedly sworn to LL that he has no interest in the race, and he’s still dealing with the fallout from his last campaign.)

Some of these contenders could choose to run even if Gray makes a bid for reelection. Others will likely take a pass if he runs again, considering his overwhelming name recognition advantage. (One Ward 7 insider even suggested to LL that Alexander would only consider a run in a special election called in the event of Gray’s sudden retirement or death, rather than dealing with the challenges of a protracted campaign.) At the very least, Gray’s decision will indelibly shape the race.

“He has served here for 30 years … so I would say we owe him that space to decide for himself,” Rasheed says.

For what it’s worth, Gray’s longtime campaign manager and current Council communications director Chuck Thies told Axios last September that Gray planned to run again, and he tells LL that he hasn’t received any indication that his boss is thinking of hanging it up. Thies says Gray last consulted him about how to prepare for 2024 back in March, and the pair agreed to revisit the question after Labor Day since the race still hasn’t really begun in earnest.

“Without fail, every time I’ve spoken with Vince, when the subject has come up, it has not been a question as to whether or not he’s running,” says Thies, who stresses he was speaking about the campaign when he was off the clock at his Council job to avoid any ethics concerns. “It’s a question about: What are we doing to prepare for [a campaign launch]? And when will it happen?”

This generally aligns with what LL has heard from others in Gray’s orbit. Most suspect Gray will ultimately choose not to run, considering he’s still dealing with the after effects of a stroke, a torn Achilles tendon, and a subsequent fall, but there is some part of him that isn’t willing to step back. After all, the list of D.C. councilmembers to voluntarily walk away from politics in the entire Home Rule era is pretty short: Sharon Ambrose, Mary Cheh, and David Grosso are pretty much the only examples in the past two decades.

“It is not out of the picture until he says ‘I’m not running,’” says Lisa Rice, a Ward 7 ANC representing Dupont Park. “And he hasn’t said that. All of the other talk about he should, he could, he shouldn’t, he wouldn’t, it doesn’t matter at all, until he and only he, not a surrogate, says he’s not running.”

Some residents aren’t ready to push him out the door just yet. Gray still has plenty of friends around the city, as do some of his top staffers (particularly chief of staff Sheila Bunn), and he undeniably has a wealth of knowledge about the workings of the legislature and city government. Whatever Gray’s recent failings, Chair Phil Mendelson’s decision to strip him of his chairmanship of the health committee earlier this year seemed like a bad look to some ward residents.

“My issue when people speak on Gray is: Have compassion, have love, have a heart, because one day you’ll be in that same position, and you don’t want people looking down on you or picking you apart and tearing you down,” says Ashley Ruff, an ANC who lives just off Benning Road NE. “You want to be built up, you want to be loved, you want to be encouraged.”

But that sentiment is not universal. LL has heard repeatedly from Council staffers that Gray is basically a nonfactor on most issues of consequence around the Wilson Building, and his decision to bring Thies into his Council office has rubbed many in the ward the wrong way. There is rising anxiety about crime in the area, but is a White guy who doesn’t live in Ward 7 (and who uses some pretty incendiary rhetoric) really the best messenger for Gray on this subject? Thies’ vocal role here has only fueled concerns that Gray isn’t paying close enough attention to his office.

“[Thies] claims to care about public safety, but you really don’t take the time to come and engage the community,” Stamper says. “If you did, you wouldn’t say half the things you do on social media, and say that you’re representing a former mayor.”

Thies, of course, waves these concerns away, and insists Gray is “100 percent able to do the job that he was elected to do and he is immersed in his work.” He will concede, however, that Gray’s physical therapy schedule remains “grueling,” and this has pulled him away from meetings that he would otherwise attend. LL wonders whether this rehab work might also make it a bit difficult for Gray to manage a campaign on top of his Council duties, but Thies says he’s never broached the subject with his boss and does not plan to. 

It’s enough to have some wondering whether Gray would be vulnerable if he does run, particularly after he only cracked 45 percent of the vote back in 2020. His three top opponents (Rasheed, Kelvin Brown, and ANC Anthony Lorenzo Green) combined for about 800 more votes than he managed on his own, suggesting there’s some anti-Gray sentiment out there.

“The most engaged partisans didn’t want the incumbent coming back last time, so I can’t imagine it would be any different this time around,” says Rice, who adds she briefly considered challenging Gray as an independent in the general election four years ago after seeing the primary results. “He and others have given their time and it’s time for new blood.”

But this is a common refrain about the city’s entrenched politicians. Gray has nearly universal name recognition and it would almost certainly take a one-on-one matchup with a strong opponent to oust him. (This is precisely the reason why Rice says she started backing a ballot initiative to bring ranked choice voting to local elections.) Thies and others argue that the George Floyd protest movement crested just as voters headed to the polls in the 2020 primary and helped candidates associated with these demonstrations (like Green and Rasheed) and hurt establishment types like Gray.

Nevertheless, some candidates seem set on running even if Gray tries again. Kelvin Brown and Rasheed have already challenged him once with decent results, and could do so again—Rasheed led the pack of challengers with a little over 2,600 votes, while Brown picked up a bit over 2,000. (LL hears that Green, who finished with nearly 1,400 votes, is not interested in the race unless Gray takes a pass, but he did not respond to requests for comment.) Brown says he would “be fibbing if I didn’t say that the thought had crossed my mind or that I haven’t been asked on a countless number of occasions,” but he hasn’t made any decisions on a run. Rasheed had a similar line, though she is sounding to LL quite a bit like a candidate. 

“People know I would mount a strong campaign with a head start on anyone else who might run, because I was the top vote getter among the challengers with a strong incumbent in the race, and that was just three years ago,” says Rasheed, who ran with the tacit backing (if not formal endorsement) of her former boss and then-Attorney General Karl Racine in 2020.

Her campaign was not so impressive as to dissuade everyone else eyeing the race, however. Some ward politicos note that Brown was a relative newcomer to ward politics in 2020 but still managed to beat Rasheed in the key precincts south of Massachusetts Avenue SE, especially in his neighborhood of Hillcrest (historically Gray’s base as well). If Gray hangs it up, this could easily open the door for a more establishment figure like Alexander or Johnson entering the race. 

After heaping praise on Gray, Johnson tells LL he’s “not sure” if he’d consider a run and that “I’m going to continue to help and do the work of the ward simply as the stakeholders want me to.” Alexander did not respond to LL’s requests for comment, but her very active Twitter profile has prompted plenty of speculation that she could be interested in the race. 

Alexander still has lots of detractors from her decade-long run in the Wilson Building, which could make a comeback an uphill battle. The same goes for Kwame Brown, of course, who by all accounts remains frustrated that his promising political career was felled by the same prosecutor who tormented Gray, Ron Machen. He’s only occasionally dabbled in ward politics (weighing in on a Ward 7 Dems leadership race back in 2019 and moderating one of the organization’s mayoral debates last year) but he’s also been getting a bit more political with his new talk show; a clip he posted in July, at the height of the debate over new crime legislation, assuring councilmembers that it’s “OK to be tough on crime” really got tongues wagging.

But he has not been as aggressive about a comeback as, say, ex-Ward 2 Councilmember Jack Evans, and there’s good reason to wonder whether this is simply gossip about one of the central figures of D.C. politics circa 2010. Brown didn’t respond to LL’s request for comment, but he told the journalist Pete Tucker he had no interest in running again last year.

Stamper is blunt about how she feels about a potential Brown renaissance: “He needs to go sit down somewhere.” Like several others LL spoke with, she’s ready to see a new generation of pols rise to prominence after so many years of dominance by Gray, Alexander, and the rest of the old guard. 

This is where Felder and Thompson could enter the picture. Felder, the Ward 7 Dems head, didn’t get much traction running as an at-large candidate back in 2014, but many around the ward believe he’s been positioning himself to try again whenever Gray steps back. He has established especially close ties with Mayor Muriel Bowser, too, leading some to worry he’d be too much of a rubber stamp for the mayor if elected. (After this article was published, Felder called LL to take issue with this characterization, noting his close working relationships with Bowser and Gray over his tenure leading the Ward 7 Dems and as a four-term advisory neighborhood commissioner. “My body of work speaks for itself,” he says.)

Thompson would have a bit more of a progressive bent, considering she’s staked out a position as a critic of mayoral control of schools in her short time on the SBOE. She also ousted a two-term incumbent, the late Karen Williams, with her 2020 state board win, so she has some political talent. She told LL only that it was “really early” to begin discussing the race, but otherwise didn’t respond to requests for an interview. 

Some observers speculate that a fresh face may prove to be a particularly attractive option for anyone newly drawn into the ward in the redistricting that took effect at the end of 2021. The ward has gradually expanded ever westward across the Anacostia River as its population has failed to keep pace with the boom in Ward 6, and that will surely change the political calculus for any candidate. The base of the voting population may still be the civically engaged seniors that have traditionally dominated local politics, but a mix of gentrification and redistricting has still changed the electorate in some meaningful ways.

“If the new voters west of the river assert themselves, with their net wealth, their privilege, their high income, high educations, then the east part of the ward may well fight against them,” says Johnson, who closely followed the redistricting debate. “You could get 50 to 60 percent turnout there, just to combat what the west of the river is doing.”

Whether it’s a generational clash pitting Gray against young faces, or a frenzied, open seat fight exposing the ward’s divides, LL does not doubt that the next year will be fun to watch. Add in the drama over Ward 8, where Councilmember Trayon White has expressed interest in running again after months of rumors about his future, and all the best political intrigue could be in Southeast next summer.

“I will say this: Sometimes the best seat in the house is in the audience,” Kelvin Brown jokes.

This story has been updated.