Credit: Photo by Darrow Montgomery

Earlier this year, At-Large Councilmember Michael A. Brown organized a youth summit that featured pep talks from minor celebrities like the winner of Survivor: Cook Islands, as well as cameos by a few of Brown’s fellow District politicians. The entertainment included a fashion show with models wearing clothes from the Gap that were supposed to show how you could be cool and office-appropriate at the same time. Council Chairman Kwame Brown did some modeling himself, vamping on the runway in sunglasses, a black shirt, a yellow tie, and blue jeans. The emcee remarked several times that Brown had “swag.” Afterward, both pols gave speeches about the importance of helping the next generation.

The episode was one of those goofy, feel-good events elected officials everywhere do every day. But for both Browns (no relation) there’s an obvious correlation between trying to help the next generation and their own stories. Michael and Kwame, as well as their colleague Harry Thomas Jr., represent the D.C. Council’s trio of legacy legislators, pols whose fathers played their own significant roles in politics. Michael’s father, Ron Brown, was commerce secretary under President Bill Clinton. Kwame’s dad, Marshall Brown, is a longtime campaign organizer and was a lieutenant to former Mayor Marion Barry. Thomas’ dad had the same Ward 5 seat his son now has. (Ward 4 Councilmember Muriel Bowser is also the daughter of an Advisory Neighborhood Commissioner, a somewhat smaller position.)

Harry Thomas Sr. in 1997(Photo by Darrow Montgomery)

In a city that won the right to govern itself only in the 1970s, the very fact of a second generation of politicians represents something of a milestone. But in a town where the local democracy stands as an achievement of the civil rights movement, the existence of political dynasties also represents something of a conundrum: How to reconcile the movement’s ideals of equality with the spectacle of candidates getting a leg up thanks to their family name.

Marshall Brown in 2005(Photo by Darrow Montgomery)

Legacy, of course, knows no party or race: Chicago has its Daleys, Ohio has its Tafts, and the United States of America—alas—has its Bushes. Now Washington has its own dynasts, too. But before we declare that the advent of multigenerational politics means the capital has become just like the rest of the country, it’s worth pausing to examine the three specific men who carry their various family mantles. A close look at their political ascents and their current challenges can tell you a lot about the District.

The contradictions inherent in how we talk about our legacy legislators might be unique to Washington. On the one hand, there’s a fealty to history—in the District’s case, to the noble movement that enabled home rule. Political strategists say each of the legacy legislators’ strongest support comes from older African Americans who remember both the bad old days and the names of the folks who helped end them. “You can’t deny that this is the next group of people stepping in,” says former Ward 1 Councilmember Frank Smith Jr., who’s also a veteran of the civil rights movement and now runs the African American Civil War Memorial Freedom Foundation and Museum. “The public is counting on them, I’m counting on them, to get this right.” Smith adds: “They come from good stock, they’re going to have good futures ahead of them.”

Harry Thomas Jr. at his father’s grave(Photo by Darrow Montgomery)

On the other hand, there’s the notion that running a municipal government is inherently nonidealistic. For all the talk about their history, the legacy legislators are the sons of officials whose careers involved the unromantic work of raising political funds, apportioning budgets, or lining up get-out-the-vote efforts—stuff that doesn’t lend itself to March on Washington rhetoric, no matter how noble the pol. Growing up, these sons were liable to have learned just as much about the short-term art of the deal as about the long-term arc of justice; politics, as the cliché goes, is the art of the possible. It’s a lesson their critics say they’ve overlearned. “The three of them have strayed from the path,” says former At-Large Councilmember Bill Lightfoot. “They believe there are certain perks that come with elected office and they are entitled to those perks.”

For all the differences among the three legacy legislators, 2011 has brought their similarities into focus. To varying degrees, all three have found themselves politically embattled during this year of municipal scandals. Also to varying degrees, they’ve benefited from public sympathy attached to their family histories. “Their fathers were political heroes when that war was being waged,” says Lawrence Guyot, a longtime civil rights and community activist.

At a time when the city’s demographics are changing fast, it’s not clear whether that goodwill is enough. The answer may reveal even more about the District’s evolving political culture. But it’ll also depend on the unique men who are Washington’s three political sons.

At the end of last year, two workers at the Department of Public Works were emailing each other about how rotten it was that Kwame Brown had put the city on the hook for two Lincoln Navigators, returning one because he didn’t like its gray interior.

“My friend I have been down this road before with egotistical politicians who don’t realize there are folks out here who will do everything they can to bring you down,” wrote supervisor Michael Biggs. “Yet, these young brothers like Brown can’t seem to get that in their heads and just march on like they are invincible.”

Two months later, the Navigator incident would be splashed on the front pages of the Washington Post and Brown would be facing the biggest tests of his political career. The episode came not long after the public found out Brown had been sued by multiple credit card companies after running up a large debt on purchases that included luxury cars and a boat called Bulletproof.

Up until the Navigator affair, Brown had lived a pretty charmed political life. He knocked off a highly vulnerable incumbent in 2004, ran unopposed in 2008, and hardly had to break a sweat to become chairman last year.

It wasn’t going to be too long, the conventional wisdom went, before we’d be calling him Mayor Kwame Brown.

“You just kind of knew,” remembers Sam Brooks, one of Brown’s opponents in the 2004 election, of Brown’s mayoral potential. “He’s such, such a good politician.”

If the mayor’s office is in Brown’s future, it’ll be quite a rise for a self-proclaimed underachiever. Growing up with his mother in suburban Virginia, Kwame had behavior problems in school. He failed the 3rd grade and was expelled from his public high school. He went to live with his father and eventually graduated from Wilson High School, where, he says, he rarely went to class.

A compact, restless ball of energy who can ooze charm and flash a megawatt smile on command, Brown has a thorough mastery of retail politics. That’s a big reason for his quick ascension to the second-highest elected position in the District. But he also owes a big debt to the political connections and know-how of his father, Marshall Brown.

Marshall is best known as one of Marion Barry’s most loyal former lieutenants—and for causing a national uproar for complaining about racism after a white colleague used the word “niggardly.” Brown was also a member of the Student Nonviolent Coordinating Committee, the grass-roots civil rights group that served as a launching pad for Barry and several other politicos.

“His gut instincts are just flat-out political,” says Smith, the former Ward 1 Councilmember. “That’s all he ever thinks about.”

Marshall helped conceive and execute Kwame’s first campaign, which out of necessity as much as design followed a grass-roots playbook similar to the SNCC’s. Kwame, who began the race with almost no name recognition and little chance of raising anywhere close to the money incumbent Harold Brazil had, hustled his way to a win by starting his campaign early, knocking on a ton of doors, and planting a lot of yard signs.

Brown family connections who’ve helped guide Kwame’s professional life include Courtland Cox, his former boss at the U.S. Department of Commerce and an SNCC alumnus who also worked for Barry; Tom Lindenfeld, a campaign guru enlisted by Marshall to help with Kwame’s first campaign; and Ivanhoe Donaldson, another SNCC alumnus and Barry aide who’s advised Kwame on campaign issues.

But for all the benefit Marshall Brown has been to his son’s career, he’s also been a burden. His suggestion that the gay rights movement is different from the civil rights movement because “you can choose to be gay” and his recent musings that newer white residents of the District are interested solely in “doggie parks” have hurt Kwame’s efforts to be a seen a politician who appeals to all parts of the city.

Some problems run deeper than glib quotations in the newspaper. The Brown family has attracted legal attention for some healthy paydays it’s won from Kwame’s campaigns. (Marshall declined to be interviewed for this article, calling me prejudiced for referring to him as a Barry lieutenant and insulting me in front of a group of high school journalism students. Kwame wouldn’t talk for this story, either.)

In 2008, an audit found, Kwame’s campaign used an outside vendor to pay his brother’s sales-coaching firm $240,000. Despite repeated requests from the Office of Campaign Finance, the Brown family hasn’t provided bank records to show how that money was spent. The D.C. Board of Elections and Ethics suspects that criminal activity occurred, and the U.S. Attorney’s Office says it’s reviewing the campaign’s finances. Marshall Brown recently told the Post that he takes responsibility for unnamed mistakes.

Marshall may wind up taking the blame for the campaign-finance problems, but the notion that his son also views politics as a means to self-enrichment may never disappear. Whether it does will depend a lot on Kwame’s political skills, as well as the District’s collective ability to forgive and forget.

There used to be a time, long before the threat of federal prosecution, when Harry Thomas Jr.’s biggest challenge seemed to be overcoming his insecurity about being a political legacy.

“Being a son of a councilmember is more of a hindrance because I’m scrutinized more than anyone else,” a 29-year-old Thomas told the Washington Times in 1989, when he was running for shadow senator. “People automatically assume things are handed to me and I have to work doubly hard to prove that I’m qualified for the positions I have obtained.”

It’s not hard to see how some people might have gotten that impression. Thomas represents the District’s dynastic politics in the most traditional sense. He shares the same name and office as his late father, Harry Thomas Sr., who served as Ward 5 councilmember for 12 years. Thomas’ mother, Romaine Thomas, was a well-respected school principal and is active in the D.C. Democratic State Committee.

Politics was embedded in Thomas Jr.’s DNA. He served as an ANC commissioner, head of the D.C. Young Democrats, and on the DCDSC before winning his council seat in 2006. His wife used to be his father’s chief of staff and has been active in running her husband’s office, too. Thomas worked on all of his father’s campaigns, once getting stopped by police with his trunk allegedly full of two opponents’ campaign signs.

So his decision to follow in his father’s footsteps and run for council surprised exactly no one.

“It just kind of happened automatically,” says Romaine Thomas of her son’s political career. “People wanted, were looking forward to him…carrying on that inherent legacy.”

The Thomas family’s life story mirrors that of many middle-class black families in the District. Thomas Sr. was born poor in Richmond, Va., came to D.C. after World War II as part of the second great migration and worked for the federal government. At night, he would work as a caterer or a waiter to earn extra money, and he built a solid middle-class life for his family.

Thomas Sr.’s legacy is that of the District’s ultimate ward boss: He busied himself solving the minor problems of his constituents—a missed trash pickup, a broken sidewalk, a relative needing help landing a city job. Thomas was legendary for driving around his ward looking for the kind of little problems he could help solve. (Also legendary: when the 70-something Thomas punched a 20-something aide who was late to a Christmas toy giveaway.)

He would also skirt city laws, though not in a big way, when it suited his purpose.

“Every time I would see Harry, he would grab my hand and say, ‘Hiya, sugar’ and give me a kiss on the cheek, and I’d take my hand away and he’d have put a five or ten in my hand,” says former Ward 6 Councilmember Sharon Ambrose of her first run for council. The cash donations kept Thomas’ name from appearing on any campaign-finance disclosure forms, Ambrose says, but they were never large enough to warrant any kind of fuss. “We weren’t talking big bucks here. In full disclosure, I do have to say I grew up on the South Side of Chicago.”

The younger Thomas long benefited financially from his father’s position in politics. In 1987, he was hired by a conglomeration funded by some of the nation’s largest food retailers and beverage makers to defeat a ballot initiative to add a deposit on soda cans and bottles. Thomas was paid at least $11,000, plus nearly $3,400 in car-rental expenses, the Post reported at the time. In 1992, Thomas was awarded a city contract worth $20,000 to provide job-training services to the District’s youth while simultaneously working to defeat a recall petition of Mayor Sharon Pratt Kelly, the Washington Times reported.

Leon Swain, who’s served twice as the city’s taxicab commissioner, remembers that during his first term, in the ’90s, there was only one paid lobbyist on taxi issues: Harry Thomas Jr. The elder Thomas was chairman of the committee that oversaw the taxi commission.

“For years, I have said this is a conflict of interest,” a cab advocate told the Post back in 1998. Dorothy Brizill, one of the District’s longest serving watchdogs, says she remembers raising conflict-of-interest issues with Thomas back in his lobbyist days. She also remembers his reply: “‘It’s no big deal. It’s not hurting anyone.’”

Thomas Jr. represented taxicab-company owner Jerry Schaeffer, who remains one of the most powerful figures in the taxi industry. Earlier this year, Thomas introduced a taxi-medallion bill that’s widely despised by many of the District’s cab drivers. The legislation is known in local taxi circles as Schaeffer’s bill.

Several months after Thomas Sr. died in 1999, his son was hired as a vice president of public affairs at D.C. General Hospital. Thomas told the Post he was hired because of his public-affairs background, not because of his father.

It clearly still bothers Thomas that people believe he’s ridden his father’s coattails. (Like Kwame Brown, Thomas wouldn’t be interviewed for this story.) At a council hearing earlier this year into the hiring of a handful of children of senior officials in the Gray administration, Thomas repeatedly gave rambling, almost nonsensical defenses of the hires.

“People said I got here only because of my father,” said Thomas. “I’ve understood what it is standing in the shadow of someone who has consistently tried to say that nepotism existed in the things I’ve accomplished, and I’ve had to do what I’ve had to do to prove that wrong.”

But Thomas has given his critics a lifetime’s supply of ammunition with his recent legal troubles. Earlier this summer, he agreed to pay the city back $300,000 after the attorney general sued him for allegedly stealing city funds earmarked for youth-baseball programs and spending the money on a luxury SUV and golf outings, among other things. Like Brown, Thomas has also attached the attention of federal prosecutors.

Thomas maintains he’s not done anything wrong. He’s been relying on the goodwill his family has built up to see him through. How long that goodwill can last is an open question. There’s plenty of chatter about a recall in his ward; possible candidates are already quietly lining up support in the event he leaves office.

The story of Michael Brown’s political legacy is on a different level than that of Kwame Brown or Harry Thomas Jr. Michael Brown comes from black political royalty. His father, aside from being President Clinton’s secretary of commerce, was a millionaire lawyer and lobbyist and the first black chair of the Democratic National Committee. A street downtown and a middle school in the District are both named after Ron Brown, who was killed in a plane crash in 1996. His son can tell stories of crisscrossing the country with presidents, working on presidential campaigns with the likes of George Stephanopoulos, and warming up a giant crowd at UCLA’s Pauley Pavilion the day before Michael Dukakis lost the 1988 election.

Unlike Thomas, Michael Brown is at ease assuming the legacy of his father. Or at least he says he is.

“I don’t live my life trying to step out of his shadow. I kind of like his shadow because he did such great work,” says Brown during an interview in his council office, which is filled with pictures of his father, including an old Pepsi ad featuring Ron Brown as a child, one of the first directed to black families. “My father had a very strong influence on my life. If he was a dentist, I’d probably be a dentist.”

Brown’s easygoing demeanor doesn’t mean he doesn’t carefully guard his image. When I once wrote on Twitter that my Google alert for “Michael Brown” was useless (because it’s such a common name), his chief of staff called me a few moments later to make sure I wasn’t mocking Brown.

It’s easy to see why Brown would be a little touchy about his rep. The comparisons between father and son haven’t always been kind to Michael, who’s been knocked for not being as smart and ambitious as his übersuccessful dad. That perception hasn’t been helped by Brown’s relatively modest legislative accomplishments and the fact that he had to drop his Democratic Party registration and declare himself an independent to win a seat on the council after losing bids for mayor and the Ward 4 seat.

“I’m always surprised Michael made it,” says one Wilson Building wag who knew Ron Brown. “I never really thought he wanted it that much.”

But while Ron Brown is best, and correctly, remembered as a major player in national politics, he was always interested and involved to some degree in local affairs, Michael Brown says. Michael says it was his father’s time at the Urban League working on social issues where Ron developed key contacts with “old-school pols,” as Michael describes them, such as former Council Chairmen Sterling Tucker, John Wilson, and David Clarke and Councilmember Charlene Drew Jarvis.

Those ties led to Ron Brown’s being named chairman of the board for the newly formed University of the District of Columbia. His local ties extended into District business, as well. While a partner at Patton Boggs, Brown set up a side business as minority contractor to a firm that sold supplemental retirement programs to District-government employees. Questions about how he’d been awarded the city contract surfaced during Brown’s confirmation for commerce secretary, and he sold his stake in the company.

Ron Brown’s dealings in District matters were part of several probes during the Clinton era. Then-U.S. Attorney General Janet Reno launched a special investigation into Brown’s financial ties to Nolanda Hill, a flamboyant Texas millionaire who would later plead guilty to tax evasion. Hill, a close confidante of Brown’s, told the New Yorker in 1997 that when Brown was at Patton Boggs, he offered his connections with District officials to “grease the problems” she was having getting permission to build a new transmission tower for her television station.

The special investigation into Hill’s business dealings with Ron Brown expanded to include Michael Brown and whether he’d been part of a scheme by a pair of Democratic fundraisers, Gene and Nora Lum, to improperly influence his father. The Lums placed Michael Brown on the board of an Oklahoma natural-gas-pipeline company, and “although he did little work for the Lums, [Michael Brown] was given company stock and paid $150,000 and a country club membership worth $60,000,” according to a U.S. House report.

The special investigation into Ron Brown ended without reporting any conclusions when Brown died. But materials from the investigation were turned over to the Justice Department’s public-integrity unit, and in 1997 Michael Brown pleaded guilty to a misdemeanor election-law charge for exceeding the legal donation limit with contributions to Sen. Ted Kennedy. Prosecutors said Brown exceeded campaign contribution maximums by giving in other people’s names and was reimbursed for the $5,000 total he gave the Kennedy campaign by the Lums’ gas company. Brown says he doesn’t recall being part of any investigation into his father, and says that he voluntarily reported his campaign contribution misdeeds to the Justice Department.

Those legal problems have proved little more than minor embarrassments in Brown’s local political career. A year after his guilty plea in 1997, he was being pressured to run for mayor. And last year, Michael D. Brown, a pudgy white man who’s quite possibly Michael A. Brown’s literal physical opposite, did surprisingly well in the at-large council primary—apparently because many voters confused him with Ron Brown’s son.

Brown has also faced problems of a different nature. This year he’s become the target of the Washington Post’s opinion writers, who questioned his integrity and industry ties after he pushed through legislation that legalized online gambling in the District but received little public scrutiny before being passed into law. Brown says he’s being unfairly attacked over a legitimate policy debate, partly because he’s African American. But he hasn’t helped his case by being cavalier about the whole thing, telling reporters there was nothing wrong with accepting bundled donations from businessmen connected to the lottery because that’s what developers do all the time.

The messy intersection of connections, politics, and money almost undid Ron Brown’s career before his death. But his son hasn’t shied away from it.

Will there be a third generation of legacy pols? The forecast looks murky.

The more immediate question is about the legacy legislators’ own futures. If Kwame Brown and Harry Thomas Jr. survive their brushes with the feds, will they still have enough support in three years to be re-elected or elected to higher office? And what sort of impact will the Post’s editorial condemnations have when Michael Brown next seeks office as an independent?

On the first question, there may be reason to hope for Brown and Thomas. Only three councilmembers, David Catania, Mary Cheh, and Tommy Wells, have called for Thomas’ resignation. It’s hard not to notice that all three are white and were born somewhere outside the District—just like every one of the council’s white elected officials.

But the fact that said demographic is growing fast as a proportion of the District electorate is a bigger problem down the line. Leaving aside the ideological differences between often affluent newcomers and the black middle-class voters who dominated the first four decades of home rule, newcomers just don’t know the history that might make them admire a family name.

In the meantime, though, family still matters. Kevin B. Chavous, 26, recently announced his candidacy to fill the Ward 7 council seat previously held by his father, Kevin. P. Chavous. And just look at who’s keeping quiet about Thomas’ troubles: a population that includes even Vincent Orange, a man who’s battled the older generation of the Thomas family as well as the younger generation of the Brown family. Those keeping quiet do so for a number of reasons, one of which is that Thomas isn’t just part of his own family (“I have confidence and faith, because I know what kind of foundation I laid for that child,” says Romaine Thomas), but also part of a larger political family.

“If a family member messes up, you still support them. You may not support what they did, but you support them as a family member,” says Michael Brown. “Even if they did something fucked-up.”