U.S. Representative Charles Rangel is fond of saying that he hasn't had a bad day since he managed to survive a nighttime attack in frigid temperatures during the Korean War.
On Tuesday, he may have to revise that assessment.
A political colossus in New York, Mr. Rangel is facing a determined opponent in a primary contest. If he loses, it will be his first defeat in more than forty years of representing a swath of upper Manhattan. It could also mark the first time since the Second World War that Harlem will not be represented in Congress by an African-American.
As Mr. Rangel, 84, fights for his political future, many see the end of an era. Dapper and congenial, he has roamed the halls of Congress since Richard Nixon was president, rising to become one of the most powerful legislators in Washington.
But Harlem – once a political factory that moulded black leaders for statewide and national office – is changing rapidly. An influx of new residents has altered the demographics of the neighbourhood, which is home not only to storefront churches and housing projects but also pricey condominiums, sushi bars and soon, a Whole Foods Market.
In recent years, the African-American population in upper Manhattan has declined as the Latino and white population increased. In Mr. Rangel's district, more than half the residents are now Latino, while 27 per cent are African-American and 12 per cent are white, according to figures provided by his office.
Mr. Rangel's main challenger in the Democratic primary, state senator Adriano Espaillat, was born in the Dominican Republic and if elected, would be the first such Congressman in the United States. (The district is one of the most heavily Democratic in the country, so for decades, the real battle has occurred in the primary phase, rather than in the general election in November.)
On the streets of Harlem, where many people have lived their entire adult lives with Mr. Rangel as their representative, there is both affection and exasperation. "I respect Mr. Rangel totally," said Yarnike Washington, 41. "He built Harlem. But his time is up."
Mr. Rangel, sometimes dubbed the "lion of Lenox Avenue" after one of Harlem's main thoroughfares, has said that this campaign will be his last and that he intends to close out his career when President Barack Obama leaves office in 2016. The son of a seamstress, Mr. Rangel dropped out of high school and earned a Bronze Star for valour in the Korean War. He later trained as a lawyer. In 1970, he defeated Adam Clayton Powell, Jr., the first African-American to represent New York in Congress.
Some of his recent troubles are of his own making. In 2010, he was censured by his fellow members of Congress for 11 ethics violations, including a failure to pay taxes and improper fundraising practices. As the investigation intensified, he gave up his post as Chairman of the Committee on Ways and Means, a hugely influential body with sway over the U.S. tax code.
Still, Mr. Rangel won re-election in 2012. This time around, however, some former friends have kept their distance. Mr. Obama has maintained a studious silence on the race, as has Bill de Blasio, New York's new mayor. Meanwhile, the local teachers' union switched its support to Mr. Espaillat, his opponent.
Mr. Rangel has come under fire for a racially tinged comment he made about Mr. Espaillat at a debate earlier this month. "Just what the heck has he done besides saying he's a Dominican?" asked Mr. Rangel.
A third candidate, Rev. Michael Waldron Jr., heads a popular church in Harlem and could siphon off some voters inclined to support Mr. Rangel.
Rose Pena, 32, and her husband, both originally from the Dominican Republic, moved to Harlem two years ago and opened Astor Row Café on Lenox Avenue. In the windows, there are signs for Mr. Espaillat's campaign. "We're excited about whoever is interested in helping the community," said Ms. Pena.
Nearby, Tony Murphy, a 44-year-old filmmaker, was drinking a cup of coffee. Mr. Rangel has been "a seminal part of the whole black political scene," he said. But "you still have to shake the tree. Politicians get complacent."
Recent polls show Mr. Rangel in the lead, but analysts caution that such surveys count for little in a contest that will depend on each side's ability to get their voters to the polls. In the 2012 primary, Mr. Rangel won by just 1,000 votes.
Vincent Morgan, a former banker who tried to unseat Mr. Rangel back in 2010, called him the "last remaining vestige of a bygone era." Still, older voters remain especially loyal to him. "I've been through that buzzsaw," Mr. Morgan said.
What's clear is that Mr. Rangel is the last of his generation of New York politicians still on the campaign trail. The others have passed away or retired, but he keeps on hustling for votes. Mr. Rangel "was a reflection of Harlem for a long time," said David Bositis, a political scientist who specializes in the study of race and politics. "But you can't serve forever."