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Vince Gray came in late, but that didn’t stop the applause. As the mayor slipped into the January community meeting at a Ward 5 church, the crowd—nearly all African Americans over 50 years old—broke into applause. And by the end of his speech, they were shouting his name.

That kind of enthusiasm isn’t unusual for the mayor of the District, but Gray hasn’t been the mayor for more than a year. In December, prosecutors finally closed the four-year-long investigation into his 2010 campaign without charging him. After losing his mayoral reelection because of the investigation, Gray is free to return to District politics.

Now Gray is coming back and is likely to run for a D.C. Council seat in the Democratic primary. The ex-mayor, who could enter either of two Council races, looks to be the most prominent candidate in a June Democratic primary that could change city politics for years.

In Muriel Bowser’s first year in office, her agenda ran into trouble. That’s thanks to an alliance between a handful of councilmembers, including D.C. Council Chairman Phil Mendelson and Ward 5 Councilmember (and potential future mayoral rival) Kenyan McDuffie. Bowser-favored legislation has repeatedly lost by a single vote.

Last month, for example, Bowser allies attempted to reinstate Bowser’s crime bill through McDuffie’s committee but were foiled by a surprise appearance by Mendelson on the Council dais. Similar Council opposition held up Bowser’s push for police body cameras and ultimately forced her to agree to a compromise that made more footage available to the public.

In the way Supreme Court watchers keep an eye on Justice Anthony Kennedy, city hall wags focus on that single vote in the 13-member body. With three Bowser-allied incumbents in challenging races this year, the outcome of June’s primaries could mean a more empowered first term for Bowser’s administration—or even less support for the mayor on the dais.

Bowser doesn’t have to worry about every race on the ballot this year. In Ward 4, Bowser favorite Brandon Todd looks set to cruise to reelection in the mayor’s old seat. In Ward 2, meanwhile, incumbent Jack Evans is showing how he became the Council’s longest-serving member—by aligning himself with the mayor and raising gobs of money to scare off any challengers.

In November, independent At-Large Councilmember David Grosso could face a Bowser-backed challenger, thanks to his frequent needling of the mayor’s agenda. So far, though, he’s only running against a Republican and Drew Franklin, an Occupy-style candidate who aims to win by “keeping it real at all times.” It’s safe to say these aren’t the kind of opponents Grosso needs to worry much about, especially when he has more than $80,000 in his campaign treasury.

For the foreseeable future, then, Bowser’s plans rest with the campaign hopes of three allies: Ward 7’s Yvette Alexander, Ward 8’s LaRuby May, and At-Large Councilmember Vincent Orange.

The Democratic primary for the Ward 8 Council seat will take place on June 14, 2016. But it’s starting to look a lot like September 1996.

The dynamics of Councilmember LaRuby May’s reelection campaign has political wags predicting a reenactment of the race that happened 20 years ago, when challenger Sandy Allen walloped incumbent Eydie Whittington. The year before that, in 1995, Marion Barry ended his post-prison redemption tour by ditching the Ward 8 Council seat for a return to the mayoral suite. Barry backed Whittington to replace him in a special election, while his wife Cora Masters Barry chaired her campaign.

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In the 1995 special election to replace Barry, Whittington and Allen faced off against a whopping 19 other candidates. Whittington ultimately beat Allen by only one vote. But mayoral support couldn’t help Whittington in the primary the next year, when Allen returned in a much less crowded field. Despite Barry’s endorsement, Whittington lost to Allen by 300 votes.

The lessons from Whittington’s defeat—and the limits of mayoral support in the city’s poorest ward—loom over Bowser-endorsed May.

Just like in 1995, May ran in a special election last year to replace Barry, this time because of his death six months earlier. Like Whittington, she had the endorsement and fundraising power of the mayor behind her both times. And like Whittington, that helped her pull out a squeaker of a win last year: In a crowded field, she beat street organizer Trayon White by 78 votes, following a recount.

Running for her seat again less than a year after the special election, May still has Bowser’s backing. In her latest campaign finance report, she reported raising more than $90,000, including $500 from Bowser herself.

Meanwhile, White, who styled himself as Trayon “WardEight” White in last year’s special election, has been busy, too. He joined Attorney General Karl Racine’s office as a community relations worker, a job that matched neatly with Racine’s own political antagonism with Bowser.

White hasn’t declared himself a candidate yet, but he’s since left Racine’s office, a likely prelude to a run for office thanks to Hatch Act rules that bar government employees from launching political campaigns. When I asked White whether he was going to run, he avoided the question, but people close to him tag his candidacy as a certainty. Since narrowly losing last year, White has won over several of his former special election opponents, including Marion C. Barry, the late mayor’s son.

But White doesn’t just have some activists in Ward 8 behind him this time. He’s backed by Racine, who doesn’t quite have mayoral fundraising powers, but can use his white-shoe law firm background to open checkbooks across the city for his candidates. White supporters say his association with Racine, which was limited to a last-minute endorsement in the special election, has expanded White’s reach in campaign season.

So 2016 might look like a lot like 1996 in Ward 8. This time, though, the incumbent isn’t the only candidate with support from higher office.

The 2014 mayoral election did not go Vincent Orange’s way, to put it lightly. Orange turned his unlikely second campaign for mayor into a celebration of all things Orange—backers were treated to a blowout launch party at Gallaudet University, complete with paeans to even minor branches of the Orange family—but voters weren’t as thrilled.

Orange came in fifth, behind Bowser, Gray, two other councilmembers, and a restaurateur with no previous experience running for office. It was the culmination of a two-year arc: Orange was busted trying to help a campaign donor’s store avoid a health department shutdown; prosecutors subpoenaed that donor’s records; and Orange was named in federal court as the recipient of an illicit “shadow campaign.” His political fortunes were at the lowest point since his failed 2006 mayoral campaign.

Now, though, Orange is the frontrunner for the campaign for his at-large seat, thanks to a divided field and a new alliance with former rival Bowser.

For a longtime District pol, Orange doesn’t have a history of convincing wins. In 2011, he won the special election for his seat with less than 30 percent of the vote. In 2012, he held onto it with 42 percent, while the combined votes of two ideologically simpatico Orange challengers nearly equaled 50 percent.

With a less-than-perfect ethical slate and a record of comical ideas that don’t come to much (at least until his long-awaited RFK-area water park finally opens), Orange looks like the ideal target. Fortunately for Orange, he’s already attracted some candidates to split the vote against him.

David Garber looks like a caricature of the kind of candidate Orange is used to defeating. A white real estate analyst turned blogger turned substitute teacher, Garber launched his campaign at Maketto, the hip H Street NE spot that describes itself as a “communal marketplace and lifestyle brand.” Not since tony Georgetown Councilmember Jack Evans launched his campaign at Logan Circle’s Le Diplomate has there been a more appropriate match between candidate and location.

Garber has been going hard on Orange’s ethical record, and it’s apparently paying off. He’s raised more than $100,000 so far, a lot of contributions for a first-time candidate.

If Orange were only facing Garber, he might have a more serious race on his hands. But he’s also running against Robert White, who came in third in 2014 for the at-large seat reserved for non-Democrats.

White, who used to work in Karl Racine’s Office of the Attorney General, has hired his former boss’ old campaign team. In an interview on WAMU, he claimed Orange’s time has come and gone.

I asked White whether he’ll win endorsements from councilmembers this cycle, since he’s running against a sitting one.

“I don’t think the incumbent has a lot of support on the Council,” White says.

For his part, Racine says he didn’t hire Robert and Trayon White with an eye toward building his own bloc on the Council. But Robert White has been pulling significant fundraising anyway, reporting more than $64,000 on Monday. That’s a hefty war chest, albeit not as much as Orange’s $180,000.

Orange isn’t raising all that money on his own. In the past year, he struck a deal with Bowser’s Green Team political set, prompting her to declare him “our friend on the Council” at a press conference. Bowser’s supporters are paying him back with contributions. Last week, ahead of the deadline to report new contributions numbers, Orange attended a spree of fundraisers, including one co-hosted by Bowser Ward 8 supporter (and occasional scandal figure) Phinis Jones.

As of this writing, Gray—Orange’s sometimes foe, sometimes ally—had not officially chosen a race.

“On the one hand, there is the path of least resistance to victory,” says one person familiar with Gray’s plans, referring to Ward 7. “On the other hand, there is Gray’s profound disdain for Vincent Orange.” But the former mayor has a more attractive race waiting for him east of the Anacostia River. And an ever-growing chorus of quotes and confirmations—all on background to media outlets around the city—certainly point away from an at-large showdown.

Heat from a federal investigation couldn’t stop Yvette Alexander from endorsing Gray’s reelection hours after he announced it in 2013. She owed him big, after all—Gray’s endorsement had once helped propel her into her current seat.

After all that history, you might expect her to be happy that her old mentor won’t face federal criminal charges. Not quite.

“I guess that’s good news for him,” a wary Alexander said hours after prosecutors announced the end of the Gray campaign investigation. “It’s never good news when someone is found guilty of a crime.”

A lot has changed since 2013. After seeing her one-time patron beaten in the Democratic primary by Bowser, Alexander moved away from Gray. As Gray’s mayoralty stumbled through a whopping nine-month lame duck period, Alexander helped chop up his remaining legislative priorities, including funding for a new hospital on the eastern side of the Anacostia River.

After being one of Gray’s most reliable Council allies, she’s switched to Bowser’s Green Team and the fundraising prowess that comes with it.

“I’m supporting the Green Team,” Alexander says. “I’m Team Alexander, but I support the Bowser administration.”

At the Ward 5 community meeting, held a day after the Washington NFL team lost in the playoffs, Gray lamented the “raw deal” given to once-promising quarterback Robert Griffin III. A career cut short by powers beyond his control? Gray might know something about that.

Unlike Robert Griffin III, though, Gray has a good chance. A poll funded by a political action committee created by Gray supporters suggests that he could beat Alexander or Orange, but that he would win by a larger margin in Ward 7.

If Gray gets into the race, he won’t need to worry about anyone other major candidates splitting his vote against Alexander.

Former University of Southern California football player Delmar Chesley has failed so far with his Hail Mary of a campaign, raising just $1,000 so far.

D.C. Democratic State Committee bigwig Ed Potillo faced better odds at first. In October, Potillo launched his campaign at a Ward 7 bed and breakfast, promising to bring new leadership to the ward (Alexander’s challengers love to gripe about an undefined lack of leadership).

Since then, though, he’s lost a campaign consultant and pulled in some dismal fundraising totals. As of Monday, Potillo’s campaign had raised less than $15,000—not exactly enough money to beat Alexander, or keep a certain ex-mayor out of the race.

If Gray gets into the Ward 7 race, his candidacy will offer Bowser a choice between a pliable incumbent or one of her most dedicated foes in the Council seat. But Ward 7 Advisory Neighborhood Commissioner Gary Butler, no fan of Alexander, is already over the rivalry.

“Me personally, I think it’s time to move past Vince Gray,” Butler says.

The question for Ward 7 is how many voters agree with Butler—and what that means for the future of the Bowser administration.