With Orange favored to retain his seat, the challengers are focusing on unseating Brown, who holds the seat reserved for a non-Democrat.
Brown has been hobbled by reports that he failed to pay his rent, taxes and mortgage on time and that his driver’s license was suspended five times in eight years.
All but one of the challengers is making a first bid for citywide office, complicating efforts to build name recognition. Each voter selects two candidates in the at-large race.
With the most campaign money in the bank and growing support in Northwest and Capitol Hill, lawyer David Grosso appears to be the strongest challenger to Brown, the son of late commerce secretary Ronald H. Brown.
Grosso, a District native, was raised by a mother who took a vow of poverty to protest war and social injustice. Although he was shaped by progressive causes — and a 20-year-old arrest for marijuana possession — he went on to be a council staffer and an executive at CareFirst.
“I am not a politician,” said Grosso, 42, who lives in Brookland. “I am just someone who wants to make a difference in my city.”
Grosso’s campaign has reopened the debate over whether the city charter should mandate that two of the council’s 13 seats be reserved for non-majority party members, which for three decades has helped lift third-party or independent candidates into office.
Brown tested the spirit of the charter in 2008, abandoning his long-standing affiliation with the Democratic Party and successfully campaigning as an independent. Grosso and another candidate, independent Leon Swain Jr., are also former Democrats, which has annoyed other candidates.
“It shows a deficiency in their character because they are gaming the system,” said candidate A.J. Cooper, an independent who is the policy director for the D.C. Campaign to Prevent Teen Pregnancy. “If you are a Democrat, then run as a Democrat.”
GOP candidate Mary Brooks Beatty argues that the council will never “curb the abuses of a one-party system” until there is more political diversity on the body.
“I just don’t see how someone who says they are for good government would go around the rules,” said Beatty, who previously worked at a bipartisan women’s leadership organization and a conservative-leaning environmental advocacy group.
Beatty got into local politics when she joined her neighbors to fight what they viewed as a nuisance liquor store on their block. She eventually became an advisory neighborhood commissioner who worked to bolster development on H Street NE.
Beatty, who describes herself as a “fiscally conservative, socially progressive Republican,” faces a steep climb in a city where just 6.5 percent of voters are registered Republican.
Though some past District GOP candidates have found support from independents and moderate Democrats, Beatty’s task is complicated by Grosso’s apparent strength in some majority-white neighborhoods.
As a teenager, Grosso first lived on a Loudoun County farm before moving with his mother into a communal St. Francis of Assisi-inspired home in Petworth, so his mother could protest for various progressive causes.
“It was very activist, very cool, very committed to making the world a better place, and that is kind of where my roots are,” Grosso said.
Grosso said he “wasn’t very good at high school” and spent much of his early 20s working odd jobs or traveling, including missionary trips to Central America. In 1993, while on a camping trip in Florida, a forestry officer arrested him for possessing marijuana.
Grosso said the experience reshaped his life, and he went on to receive a law degree from Georgetown University in 2001. After college, Grosso worked for former Ward 6 council member Sharon Ambrose, helping her to push for city financing of Nationals Stadium and to rewrite liquor laws.
When Ambrose retired in 2006, Grosso went to work for Del. Eleanor Holmes Norton (D) before being tapped to head up CareFirst’s government affairs office.
Brown has sought to make Grosso’s employment an issue in the race, arguing that the company where he works has not invested enough in the community.
Grosso, who has pledged to be a full-time council member, appears to have limited support in majority-black neighbors, where turnout is expected to be high because of the presidential race.
But two African American challengers — Cooper and Swain — are trying to muscle past Orange and Brown and could undermine both incumbents’ efforts to rack up huge margins with black voters.
Cooper comes from a prominent local family. His father, Algernon Johnson Cooper, was elected mayor of Pritchard, Ala., in 1972, becoming the first black mayor of a majority-white city in the state.
While in high school, A.J. Cooper was the host of Black Entertainment Television’s “Teen Summit” program. Cooper graduated from the University of Maryland in 2009. He is from a family of strong Democrats, but said he did not register with a party when he turned 18 in a rebellious act to prove his independence. Now, he argues, the council needs an independent voice.
“I think it’s time for something different,” said Cooper, 32, the nephew of philanthropist Peggy Cooper Cafritz. “I think I can do a better job.”
Swain, 59, is running on a platform to clean up what he views as rampant city corruption. A former District police sergeant, Swain headed the D.C. Taxicab Commission from 2007 until 2010, spearheading the transition to meter cabs.
When a cab company owner offered him a $20,000 bribe in 2007, Swain went to police. Over the next two years, Swain wore an FBI wire and collected more than $250,000 in bribes. Chargers were eventually filed against 40 individuals, including council member Jim Graham’s (D-Ward 1) former chief of staff.
Though his fundraising has been limited, Swain has made inroads at candidate forums and debates by stressing that the council needs “a cop.”
Ann C. Wilcox, who has made two unsuccessful council bids, is the Statehood Green Party nominee. A former public defender who served on the school board from 1994 to 1998, Wilcox works as a First Amendment lawyer for activist groups, including Occupy DC.
She acknowledges she faces long odds, partially due to Grosso’s appeal.
“We just have to keep building up the [Statehood Green] party so in the future we don’t get swamped by these independent Democrats,” she said.