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In Harlem, a legendary congressman — one of the most influential black politicians in modern history — faced a difficult re-election as allies backed his younger opponent in demanding a changing of the guard.

That was in 1970, when challenger Charles Rangel defeated Rep. Adam Clayton Powell Jr., a mythic figure undone by scandal and frustrated constituents.

Now, 42 years later, Rangel is the iconic lawmaker contending with perhaps his toughest re-election against challengers from within his own party who say his time has passed.

The 81-year-old Rangel had been one of the most powerful Democrats in the House, and a kingmaker in New York politics. But like his predecessor, Rangel has been weakened by scandal. He was censured on the House floor in 2010 for ethics violations, including failing to report $600,000 in income and failing to pay some taxes on rental income from his vacation home.

Shifting Alliances

Gentrification in Harlem has pushed out scores of black residents who have been Rangel's core supporters. And the boundaries of his congressional district have been redrawn to include a portion of the Bronx, making the population majority Hispanic.

Rangel will face four challengers in the June 26 Democratic primary. His greatest threat is expected to come from New York state Sen. Adriano Espaillat, who is trying to mobilize fellow Latinos behind his goal of becoming the first member of Congress born in the Dominican Republic.

Espaillat, 57, has attracted the backing of several of New York's prominent Latino politicians, including former Rangel supporters.

"I have great admiration and respect for Charlie Rangel. He is a giant," says former Rangel ally Adolfo Carrion, a former Bronx borough president and director of the White House Office of Urban Affairs. "After nearly 42 years, I think it's obvious even to Charlie that this chapter is coming to an end," he says. "Adriano Espaillat represents a turning of the page. He's got a very strong record as a state legislator. He represents an emerging demographic that is growing in the city and in the country. I think he's the right choice at this time."

Espaillat announced his candidacy this spring when Rangel was hospitalized with a back injury and infection, which forced him to use a walker and then a cane until recently. The illness caused his longest absence from Washington in a decade, contributing to concerns about his ability to continue in the job.

The pugnacious Rangel often appears astonished that his effectiveness on Capitol Hill might be questioned.

"Of course things get stagnant; people get too used to their environment, but that's why I'm in my district every week, at meetings with my constituents," Rangel said in an interview. "It's just too easy to check the record [and disprove] that my age or length of service causes a disadvantage to my constituents."

Redrawn Districts Leave Incumbents Vulnerable

The redrawing of congressional districts, which occurs every decade to reflect population shifts found in the census, has imperiled many incumbents. The elimination of some districts has pitted lawmakers from the same party against each other for re-election.

"An incumbent is more vulnerable in the first election after the redistricting. Newer voters in the district are usually more open to a new candidate," Emory University political scientist Andra Gillespie says. "Rangel's situation is a combination of age, redistricting and demographic changes within the district. You have to differentiate which one might do him in. It's kind of a perfect storm."

In New York and other large cities, longtime black officeholders are losing black constituents through population declines. Newly arrived Hispanics and whites are forming the core support for a younger generation of candidates challenging black incumbents.

Rangel has the third-longest tenure in the House after Michigan Democratic Reps. John Dingell and John Conyers. The 83-year-old Conyers, who is a liberal and the senior black member of Congress, also faces a difficult re-election in a redrawn district that now includes moderate and conservative white voters in the Detroit suburbs.

Another of the longest-serving black members, Rep. Eddie Bernice Johnson, D-Texas, recently faced her most serious primary challenge in 20 years, but won.

Old School Vs. New School

Rangel's tenure has been criticized for reinforcing a "wait your turn" culture that discourages promising new candidates. The congressman disagrees.

"Even if there was some basis for this unfounded biased accusation, you don't just say 'I don't like what's there and I want to go there,' " Rangel said.

Yet Rangel and other veteran incumbents in New York often hold a prohibitive advantage against opponents in part because of their alliances with local Democratic clubs that provide armies of campaign workers.

"People have started to think about the future of Harlem, and there's never really been a succession plan," says Democratic strategist Basil A. Smickle Jr., 40, who lives in Rangel's district. "A lot of guys, including myself, have wanted to get into politics, but this city hasn't elected anyone under 50 in a long time."

One new face in the race is that of Clyde Williams, who is making his first bid for elected office. Williams, who is black, says he's running against the "political establishment" as much as he is Rangel. But Williams isn't new to politics: He's a former Clinton White House staffer and most recently was political director for the Democratic National Committee. His wife, Mona Sutphen, was a White House deputy chief of staff under President Obama.

Williams, 50, says "decades-old problems" such as high unemployment and gun violence have persisted in the district. Last year he released a poll in which 70 percent of respondents in the district wanted new leadership. He says his campaign has knocked on the doors of 25,000 households.

"The political establishment is pretty much set up to protect the status quo and get incumbents re-elected, and not establish new leadership," Williams says. "I have the utmost respect for anybody who gives their life to public service ... but at the same time, there's a time when new ideas are needed."

Rangel says flatly: "Being new doesn't mean a damn thing."

Waning Influence

Rangel and Conyers are the only two founding members of the Congressional Black Caucus still in office. Unseating them would nearly complete the caucus's transition to a generation of members that ascended well after the height of the civil rights movement. Supporters say their departures would weaken the caucus's ability to influence legislation, particularly policies that significantly affect African-Americans.

"These are two men who, because of their seniority, can speak to truth to power, and power would listen. You lose that when you lose men or women of that caliber," says Democratic strategist Art Collins, a board member on the black caucus's nonprofit and chairman of its think tank.

But with the Republicans expected to maintain control of the House after the November elections, Rangel's and Conyers' influence is limited.

Some in Washington see Rangel's struggles to raise campaign funds as another clear sign of his waning influence since his censure. He had collected just $67,000 in the latest three-month reporting period ended March 31. His campaign had $226,306 in the bank.

Williams, the former DNC official, led the field with $284,644 raised during the same period and had $208,058 in the bank. Espaillat raised $62,055 and had $56,292 in cash on hand.

The Rangel and Espaillat campaigns have waged a battle over high-profile endorsements, though Rangel says endorsements "don't really mean that much."

But it's hard to ignore the fact that Rangel hasn't received the backing of Obama or Bill Clinton, who taped a campaign message for Rangel in 2010. Obama has endorsed other Democrats facing primary challenges, including Conyers and Johnson.

Obama appears to have distanced himself from the congressman since his censure, although they have had a strained relationship since 2008 when Rangel supported Hillary Clinton for president and once said of Obama: "This ain't no time for a beginner."

Asked why he thinks Obama hasn't endorsed him, Rangel told NPR: "Listen, I am as good as any legislator that you have met or talked with, but a psychiatrist I am not. I have absolutely no clue."

A surprise Rangel endorsement has come from a past opponent — Adam Clayton Powell IV, the son of the legendary congressman who lost to Rangel in 1970.

The younger Powell lost to Rangel in 1994 and 2010 and had frequently attacked him as out of touch with his district and "corrupt." But all appeared to be forgiven at a recent Rangel campaign rally.

"We have never had any animosity, unlike the perceived animosity from some in the public and in the media," Powell told the crowd. "We have always been friends."

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