After Adrian Fenty won the Democratic nomination for mayor in 2006, his campaign strategist, Tom Lindenfeld, asked whom he would support in the crowded race to replace him on the D.C. Council.
“Muriel Bowser,” Fenty said, referring to the then up-and-coming but little-known activist whose name was about all Lindenfeld knew.
“Then I am, too,” Lindenfeld responded, hewing to the logic that if Bowser was good enough for the boss, then she was good enough for Lindenfeld.
Eight years later, Lindenfeld was high-fiving Bowser on the night she captured the Democratic nomination for mayor, a once improbable achievement that he helped make possible as her blunt-talking, wise-cracking strategist.
In a city teeming with consultants advising candidates from New York to Albania, Lindenfeld is that rare breed of paid strategist who delves in the fun house otherwise known as District politics.
After 35 years on the campaign circuit, he knows his way around K Street, has held a fancy title or two with the Democratic National Committee and has spent years tarmac hopping for the likes of Bill Clinton and Barack Obama.
But what sets Lindenfeld apart is that he does not need a map to find, say, Deanwood, the politically important black neighborhood on the District’s east side; that he understands that something known as Precinct 66 in Ward 5 is the city’s most historically active on Election Day; that he can paraphrase the wit and wisdom of one Marion Barry.
Such as: “The only qualification for being mayor is winning the election,” a mantra Lindenfeld likes to repeat when a client’s credentials are challenged.
Since 1998, Lindenfeld, 59, has worked as a paid strategist for three of the District’s four Democratic nominees for mayor, two of whom — Anthony A. Williams and Fenty — won the job.
Bowser is Lindenfeld’s first mayoral client in the District facing a general-election challenge. But in a city ruled by Democrats, Lindenfeld betrays little concern about her opponent, Council member David A. Catania (I-At Large), who promises a vigorous campaign.
“At the end of the day, he’s unlikely to run,” Lindenfeld said. “He’s unlikely to tilt at windmills and take on a race that he can’t win.”
Thick-shouldered, with a machine-gun cackle and a longshoreman’s taste for the well-placed expletive, Lindenfeld prefers jeans and sneakers to suits, and he will never be described as an organization man — sometimes to his detriment.
“He’s not a Washington guy,” said David Axelrod, Lindenfeld’s former partner and a former senior adviser to President Obama. “He will alienate everyone in his way until he wears them down to get his way. It’s not a function of ego. It’s a function of passion and a desire to succeed.”
Lindenfeld’s best-known feud originated four years ago when Fenty squandered his reelection bid. Two days after Fenty’s defeat, Lindenfeld was quoted in The Washington Post accusing his client of “political malpractice” and blaming him for the loss to Democratic challenger Vincent C. Gray.
“Remind Me Not to Hire Tom Lindenfeld for My Mayoral Campaign,” read the ensuing headline on an Atlantic Monthly column. The columnist recommended that future clients be “very nice” to Lindenfeld lest he “screw you in public on the worst day of your life.”
Lindenfeld’s attack still infuriates some Fenty loyalists, including those who work alongside the consultant on Bowser’s campaign.
“If Tom was asked today, he would not publicly say what he said,” said Bill Lightfoot, Bowser’s campaign chairman, who served Fenty in the same role. “He may still believe it, but I don’t think he’d say it. In fact, I know he wouldn’t.”
Lindenfeld, while acknowledging that his remarks were “too raw and too soon for some people,” expressed no regret.
“There was nothing that I said that was wrong,” he said.
On the morning of the 2014 Democratic primary, Lindenfeld was where he often is on Election Day — behind a chain-link fence in a parking lot crowded with dozens of rented vans and three portable toilets.
Bowser’s green-and-yellow campaign signs were plastered all over the lot near Nationals Park. Her name was emblazoned on the T-shirts and baseball caps worn by most of her campaign workers.
Lindenfeld wore a black pullover and his usual jeans. He is not a guy who wears the team colors, no matter what team he’s on.
Since November, Bowser’s campaign has paid Lindenfeld about $80,000, mainly to devise an operation to turn out voters. Working with campaign manager Bo Shuff and others, Lindenfeld helped target about 50,000 prospective supporters and organized ways to reach them in the weeks leading to the election.
“All right. Who’s ready?” Lindenfeld shouted, summoning the men and women who would be driving across the city in rented vans, each packed with canvassers who would knock on doors to prod voters to get to the polls.
“This whole operation rises and falls on you,” Lindenfeld shouted. “Bottom line: Either we do this right, or we don’t make it.”
Lindenfeld’s streetwise shtick is a bit of a puzzle to friends who know that his father was a physics professor and his mother was an artist, and that he grew up in Princeton, N.J., a town where, as his wife, Anne, said, “You can’t go into the coffee shop without a doctorate.”
He caught the political bug in ninth grade, skipping classes to join antiwar demonstrators occupying buildings on Princeton University’s campus. At 17, he volunteered for George McGovern’s presidential campaign. He worked for Mo Udall’s bid four years later.
His many interests did not include the classroom, which may explain why he never got a high school diploma. Instead, he liked to play chess for money and was fascinated by society’s seamier aspects, working with felons, prostitutes and drug addicts at halfway houses in Trenton, N.J., and San Francisco. At 22, he got around to enrolling in college, and he obtained a degree from Princeton.
Lindenfeld spent the next decade working in the less-than-genteel climes of New Jersey politics, before becoming a director at the DNC. In 1994, he formed a partnership with Axelrod, with whom he helped direct campaigns across the country, including Patrick J. Kennedy’s first congressional race, in Rhode Island.
Williams, then a political neophyte running for D.C. mayor, hired Axelrod and Lindenfeld in 1998 to help write ads and organize voter turnout.
“Five minutes into the first meeting, Tom’s telling Tony, ‘Here’s what you need to do,’ ” recalled Max Brown, also part of that campaign. It was difficult, Brown said, to get Lindenfeld to stop talking.
Axelrod and Lindenfeld soon separated, but they worked together on Obama’s 2004 Senate race in Illinois. Lindenfeld helped to run the floor operation that year at the Democratic convention, where Obama gave the speech that first surrounded him in presidential buzz.
Axelrod rode Obama to a White House job and fame. Lindenfeld remained active in national politics, even as he worked on local races in cities such as Philadelphia and Atlanta. But he found a niche in the District, the city that had become his adopted home.
“Mayor’s races are the most important races,” he said. “People care about their mayor. The mayor works on things that affect their lives. I like all that. It’s very immediate and important.”
The niche had the added benefit of being occupied by few other strategists.
“There are more political consultants per square foot here, but they don’t know the city,” Lindenfeld said. “Ask them if they’ve been to the IHOP in Ward 8 or the Denny’s in Ward 7 — they wouldn’t know what you’re talking about.”
His choice of candidates to advise — Williams, Fenty and Bowser — share a trait. All three, he said, “ran races that appealed to voters throughout the city,” an approach that is important in a place as racially divided as the District.
As with most things political, Lindenfeld speaks with the confidence of a man accustomed to being right. But sometimes he is dead wrong.
For months, for example, he predicted that Gray would not seek reelection, contending that the 2010 campaign scandal posed too daunting a hurdle.
Then, in December, the mayor announced that he was running.
Lindenfeld beat back the ensuing rounds of razzing with his cackle. But his view of the race did not change.
District voters, he contended, have always voted for change. Only two of the city’s mayors — Barry and Williams — have won reelection.
“People are ready for a new mayor,” Lindenfeld insisted, holding on to his argument even as Gray led in the polls, then as Bowser pulled even just before voting began.
“The bottom line is,” he promised a worried colleague the day before the election, “she’s going to win. We’ve got it.”
Five days after the election, Lindenfeld drove to a meeting hall in an Anacostia church, and he applauded as the city’s Democratic leaders toasted Bowser at a unity breakfast.
The nominee sat with her aides and family at a table in front of the stage. Lindenfeld worked the edges, hugging old friends, shuffling his feet and appearing as though he wanted to be liberated from his blue blazer.
The speeches droned on.
A friend approached and introduced a reverend who confessed to a simmering political ambition.
“Is it possible we can talk?” the reverend said.
“Sure,” Lindenfeld said. He smiled and handed him his business card. “We’ll talk.”