D.C. Council candidate Brandon Todd smiles while listening to Ward 4 competitor Renee Bowser during a straw poll. Todd’s connection to Mayor Muriel E. Bowser is a source of contention. (ASTRID RIECKEN/For The Washington Post)

Front-runners in two races that will remake the D.C. Council share a powerful history with Mayor Muriel E. Bowser.

When Bowser (D) announced her candidacy more than two years ago before a group of supporters, one was a young aide who snapped pictures and posted them to Instagram. Another raised her arms, cheering loudly. The two went on to become key players in electing Bowser: one her prolific fundraising chief, the other an operative who coordinated Bowser’s campaign in Southeast Washington.

Brandon Todd and LaRuby May are now benefiting from Bowser’s decision to return the favor. Both sides may win from the arrangement. With Bowser’s help, Todd and May are poised to take on their most important roles yet: allies for the mayor on the D.C. Council who could tip the balance on key votes in favor of their old boss.

With early voting for the
April 28 special election beginning on Monday, a contest once expected to focus mostly on which candidate would replace the late Marion Barry has instead turned on another question: If Bowser’s close allies win his open seat along with the one she left behind, just how powerful could the District’s new mayor become?

As Bowser’s administration passes the 100-day mark, she has already proved to be more shrewd than many of her competitors expected last year.

LaRuby May answers questions at a candidate forum held during the straw poll for Ward 8's open city council seat in Washington on April 1. (J. Lawler Duggan/For The Washington Post)

The former Ward 4 council member has upended the leadership of the region’s troubled transit agency, working from inside out to blow up a search for a new Metro chief. She has maneuvered to consolidate legal authority over land deals and new legislation inside her office — and away from the city’s first elected attorney general.

And if all goes Bowser’s way, in a matter of weeks, two of her closest campaign confidants could take seats on the D.C. Council representing Wards 4 and 8, casting deciding votes on her $12.9 billion budget plan.

Bowser’s outsized influence on the two council races cuts both ways; it has emerged as the top issue in both local campaigns, galvanizing critics both in Bowser’s home Ward 4 and across the Anacostia River in Ward 8.

A flood of corporate fundraising, political endorsements and ready-made armies of volunteers that flowed from Bowser to Todd and May have left opponents claiming that Bowser has rigged the election.

“It’s been undemocratic — the mayor’s choice is not the people’s choice,” said Stuart Anderson, a community organizer who last week became the third person to drop out of the race against May in Ward 8, where Barry’s death in November left a council vacancy.

Anderson urged fellow candidates in a crowded field to do the same and to rally around a Barry understudy, Trayon White, in an attempt to block what he said was Bowser’s handpicked successor in May. “The idea of the mayor having another piece on the chessboard — that should be troubling to everybody.”

Neither council victory is assured for Bowser. Nearly a dozen candidates remain on the ballot in each race — including, in Ward 8, Barry’s son, who will be listed on the ballot as Marion C. Barry.

But in an off-election year in which turnout is expected to be light, candidates’ ability to identify potential voters, and then to get those voters to polls, will be key. On that score, Todd and May have an unmatched advantage.

The two are drawing on fresh voter lists from Bowser’s win in the fall as well as endorsements from a laundry list of labor unions, businesses and environmental groups that backed Bowser. With contributions from many of her same donors, the two have also amassed huge fundraising leads that they can tap in the campaign’s final weeks to advertise and underwrite fleets of vans and buses to drive seniors and others to the polls.

The two have also demonstrated that they can turn out voters. Both Todd and May crushed rivals in straw polls held early this month.

With those advantages, as well as her personal connections in Ward 8, May said in an interview that she is confident of victory, even as she acknowledged spending considerable time with voters addressing concerns about her close ties with Bowser. “People ask it overtly,” said May. “ ‘Pocket-vote,’ ‘lapdog,’ — I get it all the time.”

But May says that her first responsibility would be to voters — not the mayor.

“No one will ever have to question my motives. . . . I will be on the side of Ward 8,” she said.

May, 39, heads a nonprofit organization that focuses on real
estate development and early childhood education. She first met Bowser when they worked together on former Mayor Adrian M. Fenty’s unsuccessful 2010 reelection campaign.

In 2013, Bowser named May her Ward 8 field coordinator, and May responded with a promise to help Bowser win a straw poll seen as an early test of campaign strength. Bowser bested then-Mayor Vincent C. Gray (D) — a win that became a turning point in the primary, undercutting Gray’s assertion that he was the party’s obvious incumbent for the nomination.

It also reflected a shift in black-majority Ward 8, where high ­unemployment and poverty have defined the area for decades, and where voters have long been suspicious of politicians from elsewhere in the city.

A win for May, a native Floridian who has lived in Ward 8 for
13 years, could offer more evidence of that shift.

“I’m born and raised here; she doesn’t even. She’s from Florida,” said Jauhar Abraham, another candidate who dropped out this month. “She’s a developer and a lawyer and, to me, a developer who is not from D.C. is like kryptonite to Superman.”

Similar sentiments permeate the Ward 4 race, where Todd has been criticized for closely following Bowser’s campaign playbook. He has limited appearances at debates, saying he can be more effective going door to door, and only Saturday published a partial list of platform positions, saying he will maintain the course charted in many areas by Bowser.

He even adopted Bowser’s same shades of green and yellow as his own, and on his first mailer he announced: “Continuing the progress.” The flier has a picture of Bowser as big as Todd’s.

“I think most people believe my alignment with the mayor is a good thing,” said Todd, who as of last month still had $300,000 in the bank, more than triple any competitor.

“I can pick up the phone and call the mayor and tell her, ‘This is the way that Ward 4 needs to go,’ ” he said.

Todd, 31, started as Bowser’s council office special assistant, then communications director, reelection campaign manager, and in recent years, the face of her office as head of constituent services.

If elected, he would become Ward 4’s latest protege-turned-council member, following Bowser’s ascension to the council seat from her spot on Fenty’s campaign.

Douglass Sloan, another candidate who has held positions in the administration of former Mayor Anthony A. Williams, on the council and with the NAACP, argued in his closing statement at a debate last week that Todd, the apparent front-runner, would never go against the mayor, whom he “owes his entire political career to.”

Todd said there may be occasions when he must go against the mayor, but he agrees with most everything in her budget, including more funding for Ward 4 schools. He also supports her plan to make clear that the mayor’s counsel can review city contracts and legislation. That’s something the attorney general opposes and could present an ­early test of Bowser’s strength on the council.

Bill Lightfoot, a former council member who was Bowser’s campaign chairman, said he does not expect Todd or May to be rubber stamps for Bowser, particularly on issues with less support in Wards 4 and 8, such as the streetcar.

“Muriel will have to convince them that it doesn’t hurt them in their ward or leaves certain needs unmet,” he said.

Asked about the potential of having two pro-Bowser colleagues on the council, Chairman Phil Mendelson (D) cautioned that neither Bowser, Todd nor May should expect much of the arrangement should they win.

“To the extent that a patron like the mayor expects that she can pull strings, they are working against the dynamic needed in any legislature: consensus,” he said. “And if the person elected intends to do only what the mayor wants — equally, he or she is quickly going to find that they will be marginalized.”

But is the mayor’s effort to elect close confidants shrewd? Aggressive? “I’m not going to say which,” Mendelson said. “But if you don’t take risks, you have less of a chance of being successful.”