Barack Obama stood at the lectern, trying to figure out what to say — or at least how to say it. He started speaking, then stopped, then started again, each time searching for the right tone, the right cadence, the right words.

The audience was a small group of advisers, including two African American scholars who were counseling him on how to get his message across most effectively with black voters. Obama, whose memoir years earlier had explored his mixed-race background and search for racial identity, wanted to connect with African Americans but remain true to his own style and voice.

“I can’t sound like Martin,” Obama said at one point, according to the scholars. “I can’t sound like Jesse.”

Obama was still more than a year away from becoming America’s first black president, but already he was parsing that identity in his mind.

“He was trying to be Barack, and to not try to be someone else,” said Harvard law professor Charles Ogletree, a longtime Obama mentor who attended the June 2007 strategy session at a downtown Washington hotel, a rehearsal for a Democratic candidates debate at predominantly black Howard University.

The session was an early preview of a struggle that has sometimes confounded President Obama, sometimes energized him, sometimes disheartened him during the course of his presidency: How do you lead a nation in difficult times while embracing your unique place in history? How do you balance the duties of the presidency with the enormous expectations of people who look like you and feel pride in your achievement but may have unrealistic hopes and needs you can’t meet?

“It’s been more challenging than he or black America or black leadership thought it would be,” said the Rev. Al Sharpton, the longtime civil rights activist who has emerged as one of Obama’s most trusted black allies.

Obama rarely discusses his innermost feelings about being the first African American to occupy the Oval Office, according to friends and associates, preferring to keep his thoughts closely held, shared with only a select few. He has shown himself to be drawn to the symbolic, or even aspirational, aspect of his presidency.

One of the iconic images of his tenure is a 2009 photograph of Obama leaning down to let a 5-year-old black boy, Jacob Philadelphia, touch his hair. The boy wanted to see if his hair felt like the president’s. The image, captured by White House photographer Pete Souza, has been on display ever since, just outside the Oval Office in a hallway that Obama passes through regularly.

“He knows that a lot of young black, white, Latino, Asian and Native American children will grow up thinking it’s perfectly normal for the president of the United States to be African American,” said Valerie Jarrett, his longtime friend and senior adviser. “He recognizes that little black children can see their possibilities through his accomplishments.”

Massachusetts Gov. Deval L. Patrick, the first black governor of his state and an Obama friend, is one of the few with whom the president has commiserated. But even with him, Obama is cautious, leaving it to Patrick to bring up the issue during their conversations.

“He is very determined to be the president of everybody,” Patrick said, “and very conscious about the efforts of some people to put him in a box.”

That challenge has made matters more difficult at times for this president, some friends say. A key white ally, AFL-CIO President Richard Trumka, said race has been “confining” for Obama, forcing him to use milder language than he sometimes would like and to be self-conscious about how to engage certain subjects such as poverty and inequality, even the coarseness of the political environment.

When former House Speaker Newt Gingrich was labeling Obama “the food-stamp president,” to the applause and laughter of audiences during the Republican primaries, many Democrats were outraged, considering it racially coded language.

“He couldn’t respond to that,” Trumka said of Obama, “because the instant he does, it becomes a racial fight. People look at everything he does through the race lens, and that makes it pretty tough on him.”

Gingrich had a different take, calling it “bizarre” to assert that his reference to Obama as the “food-stamp president” was racial. He said that many whites participate in the program as well and that he would have happily made the charge against any Democratic president, regardless of race. Republicans have often struggled to find ways to attack Obama, Gingrich added, but not necessarily for racial reasons.

“Obama’s great strength, which has been very real, is that he comes across as a nice man, without regard to race,” Gingrich said.

If the election of four years ago put to rest the notion that the United States was not ready to elect a black president, this year poses a new question: Can an African American president, after four years as a fixture in Americans’ lives, win reelection?

For many blacks and other Obama allies, proving that the first time was not a quirk has become almost as important a landmark as the history made four years ago. It would be an affirmation of the 2008 achievement, coming despite what many African Americans interpret as indications in some places of discomfort with a black president — such as a rise in anti-government militias since Obama’s election, or even threats to Obama’s safety, such as the 2011 incident in which a man pulled up his car south of the White House and fired an assault rifle at the residence.

The electoral landscape, however, has gotten more difficult for Obama, with the 2012 presidential election shaping up to be the most racially polarized since 1988.

The president trails Republican Mitt Romney by 23 percentage points among white voters, according to a Washington Post-ABC News national tracking poll released last week. At this stage of the 2008 campaign, Obama trailed Sen. John McCain (R-Ariz.) by eight percentage points among white voters.

At the same time, the Post-ABC poll shows the president winning 79 percent of non-white votes, including the near-unanimous support of black voters. This is similar to the dominance Obama displayed among minority voters four years ago.

It is difficult to know what factor Obama’s race has played in the drop in white support seen in the polling; he won 43 percent of white votes in the 2008 election, including 41 percent of white male votes — a feat unrivaled by a Democrat since Bill Clinton in 1996.

Win or lose, the electorate that decides his fate Nov. 6 will be far more racially divided than the one that propelled him into the history books.

If Obama appears to take in stride the many challenges of being a “first,” interviews with friends and associates who have been in private meetings with him offer a window into how he thinks about race and the difficulties of inhabiting this unique role.

The ‘beer summit’

By the time Charles Ogletree was ushered into the Oval Office, there was much to talk about, a lot on Obama’s mind. The president had been thrown off-stride months earlier by a racial controversy he willingly entered, and he was still feeling the effects.

On July 22, 2009, Obama was asked at a news conference that was largely about health care to comment on an incident involving the prominent black Harvard professor Henry Louis Gates Jr., who was arrested at his home by a white police officer responding to a 911 caller’s report of a break-in.

“It’s fair to say, number one, any of us would be pretty angry,” Obama said. “Number two, that the Cambridge police acted stupidly in arresting somebody when there was already proof that they were in their own home. And number three, what I think we know separate and apart from this incident is that there is a long history in this country of African Americans and Latinos being stopped by law enforcement disproportionately.”

Then came the fusillade. Law enforcement organizations accused Obama of stepping into their business and drawing conclusions about an incident when he did not have all the facts. Glenn Beck, the conservative commentator, charged that Obama held a “deep-seated hatred for white people.” And on it went.

Black supporters urged him not to back down from his remarks that racial profiling remained a vexing problem, but for Obama it was complicated. Many of his allies believed that the birth of the tea party movement was in part due to discomfort with a black president. Yet, public opinion surveys were starting to show steep drops in his job approval rating among whites, and his natural instinct was to find conciliation. Hence, a “beer summit” that brought Gates together in the Rose Garden with his white arresting officer, Sgt. James Crowley. The event was mocked in some quarters and provided juicy material for the late-night comedy sketchers.

Ogletree, Obama’s old friend and mentor, had proved himself wise in sorting through the complexities of race and identity. And so months after the Gates episode, the two sat in comfortable chairs beneath a portrait of George Washington and discussed the high wire Obama often felt he was walking as a black president.

He told Ogletree that he was ready to worry less about the consequences of being labeled either an angry black man or a black man unwilling to embrace his race. He wanted to take more chances and not fret so much about the fallout.

“He’d learned from earlier mistakes, and he was much more confident about who he was,” Ogletree said.

While many Americans may see a president who plays down the significance of race in public, Obama is often more assertive on the subject in private, according to friends and associates. He has been defiant, even defensive at times, when his black bona fides have been challenged.

An example is his July 2010 conversation with Shirley Sherrod, the black Agriculture Department official who was forced by agency officials to resign over remarks she made about white farmers that turned out to have been presented out of context in video clips.

It was an embarrassment for the administration and personally for Obama, who publicly expressed his regrets. But his private conversation with Sherrod a few days later did not go well — at least from her perspective.

“I can understand what you’ve experienced,” the president told her, according to Sherrod’s recollection.

Sherrod wasn’t buying it. She was born and raised in rural Georgia during segregation. Her father was killed by a white farmer when she was 17, and she was deeply connected to the Southern civil rights movement. She had wept for joy when Obama was elected, overwhelmed by the sight of a black man reaching such heights in a country not that far removed from the days of separate but equal schools and segregated lunch counters that she had fought so hard against.

Now, in a sense, she had become an ironic victim of that success, unfairly tossed aside by bosses who seemed hypersensitive to any racial controversy and its potential impact for the African American in the Oval Office.

Sherrod still supports Obama and plans to vote for him. But, as she later wrote, she now worries that a president once thought by many to transcend race was actually “terrified” by it.

“You don’t understand issues the way I do,” she recalled telling Obama. Sherrod, who described the exchange in a book published this year, said she told the president that “we are coming from different places.”

The president insisted that Sherrod was wrong. “If you read my book, you’d see,” he said, according to Sherrod, referring to his 1995 memoir, “Dreams From My Father.”

Administration officials declined to comment on the conversation.

Addressing the National Urban League that summer, Obama expressed regret about how the Sherrod matter had been handled. He called Sherrod an “exemplary woman” who “deserved better,” and he said that her experience should be a model for race relations.

The treatment of Sherrod clearly pained Obama. Yet, privately he also was agitated by suggestions that he was a stranger to black struggle. Critics such as the scholar Cornel West and talk-show host Tavis Smiley were touring the country accusing the president of failing to provide enough help for underserved and economically distressed African Americans.

West, who had been an adviser and visible supporter of Obama in 2008, including as a participant in that 2007 pre-debate session, happened to be seated in the front row for the president’s Urban League speech. Afterward, Obama stepped into the crowd and made a beeline for West. Photographers captured the two men shaking hands. The pictures did not reveal what was actually happening — Obama proceeded to upbraid the professor for his recent criticisms, according to West.

“I’ll be damned, telling me I’m not progressive enough,” West recalled Obama saying to him.

The White House declined to comment on the encounter. Aides say they feel West’s critiques have been unjustified, and they say they would welcome him to the White House for further conversation.

As for West, the encounter left him speechless, “cool on the outside but burning inside,” he said.

‘Because of you, John’

If dealing with black disgruntlement sometimes has frustrated Obama, there have been many private moments in which he has been filled with black pride — and times when he has sought to link himself directly to the African American experience.

Black visitors sometimes enter the Oval Office and just break down in tears, moving Obama in the process. Often when that happens, aides say, Obama keeps his own emotions to himself, tucked away for a conversation later with his wife or daughters.

In the early months of his tenure, Rep. John Lewis (D-Ga.) came to visit. Forty-six years earlier, Lewis and Martin Luther King Jr. stood in the same Oval Office with President John F. Kennedy, reflecting on the March on Washington and King’s dramatic “I Have a Dream” speech.

The 72-year-old congressman, often mentioned by Obama as a personal hero for his work as a young civil rights organizer, remarked on the “distance we’ve traveled” from those difficult days to Obama’s ascent. Earlier, on his Inauguration Day, Obama had walked over to Lewis’s seat at the traditional congressional luncheon, leaned down and scrawled a message on Lewis’s program: “Because of you, John.”

In their Oval Office exchange, Obama nodded and smiled at Lewis’s recollection, cracking a joke about whether the carpet had been cleaned since the Kennedy era.

Months later, in January 2010, the Obamas hosted an intimate Martin Luther King Jr. Day observance in which they met with a small group of civil rights activists who had attended the 1963 march on the Mall.

The president and his wife, Michelle, sat at a long meeting table in the West Wing, surrounded by about 20 guests, many of them 80 and older, along with their grandchildren and nieces. The event had been billed as an “intergenerational” conversation, and the Obamas were definitely among the youngest in the room; the president was 2 years old when the march took place.  

“We just thought it would be nice to get together briefly and hear from some of our elders,” Obama said. He asked what “we, who are the beneficiaries of all that work, should be thinking about that period.”

The first couple asked questions of everyone sitting at the table. They heard vivid stories about how terrifying it was to participate in mass demonstrations, with threats of violence and arrests, that decades later are remembered more for the feelings they inspired and changes they accomplished.

“It seemed surprising to [Obama] to hear people say their mothers and fathers had told them not to go,” said King biographer Taylor Branch, one of the guests at the session.

One participant was Dorothy Height, 97, who wore a shimmering blue hat and glittery earrings. She sat across from Obama and told the president at one point that “of course, you’re a part of that great progress” begun by civil rights fighters decades earlier. Four months later, Obama would deliver a stirring eulogy at Height’s funeral, describing her role in the advancements that “ultimately made it possible for Michelle and me to be here as president and first lady.”

There is no recording or official transcript of the entire Roosevelt Room meeting. A brief video clip of Obama and Height can be found on the White House Web site, but aides decided to put the session off the record so participants felt more comfortable speaking bluntly.

The line from King to Obama was not lost on those at the King Day observance.

It is a connection Obama frequently embraces, quoting King in speeches and often citing his writings, such as “Letter From Birmingham Jail,” during private meetings with civil rights activists. Last year, Americans saw the once unimaginable scene of a black president dedicating a new monument on the Mall to King, without whom, he said, “we might not have had the courage to come as far as we have.”

Yet there is a tension in the connection.

Despite Obama’s past work as a community organizer, a background that inspired many liberal activists to initially see Obama as one of their own, he has made clear that as president he has broader obligations than social activism.

Clayborne Carson, the Stanford University historian tapped by King’s widow to archive and study King’s papers, said Obama seems to relate most closely to King’s earlier approaches, when he focused on more universal themes and tried not to alienate whites. King took greater risks later in his life, Carson said, launching the Poor People’s Campaign and opposing the Vietnam War.

“What we’re seeing is [Obama] likes the early King, which was about coalition-building and the idealistic things he talks about in the ‘I Have a Dream’ speech,” Carson said. “But the later King, where he begins to realize that you have to confront the realities of American society and you can’t just wish them away, that’s where they differ.”

After the discussion that day in the Roosevelt Room, Obama led the group into the Oval Office. He personally pushed Height’s wheelchair across the hall.

A hush fell over the room as the group viewed the latest addition to the Oval Office wall, hanging right over a bust of King — a rare, original copy of the Emancipation Proclamation, signed by President Abraham Lincoln, that freed the slaves 145 years before the country would send a black man to the White House.

A ‘walk between the raindrops’

The Obama presidency has created difficulty for some black political leaders, who have wanted him to succeed but have not always been happy with his policy prescriptions or the pace of change. Many represent constituencies that are largely black and that wonder: Why can’t the black president do more?

Few have grasped Obama’s quandary as well as Rep. Emanuel Cleaver II (D-Mo.), chairman of the Congressional Black Caucus and the first black mayor of Kansas City. Cleaver recalled his mayoralty as being a “walk between the raindrops,” always making sure to appoint both whites and blacks to prominent positions, and advocating for the African Americans who made up his political base while never going so far as to alienate whites.

In a Washington Post opinion column a few weeks before Obama’s inauguration, Cleaver had warned African Americans not to expect special treatment, noting that Obama “will not be the nation’s highest-profile civil rights leader. He will be the leader of the free world.”

By the spring of 2011, with black unemployment remaining stubbornly high and the full scope of home foreclosures and declining home values taking their toll on African American neighborhoods, some Black Caucus members were starting to hear gripes from constituents. What were they doing to persuade the president to help? Didn’t they have access to Obama?

The black lawmakers heard about meetings Obama was having with Hispanic legislators, who were pressuring the president to halt deportations of many young illegal immigrants. Those sessions had grown testy, with anger spilling out into public view through mass demonstrations and marches at the White House gates. The president had referenced his race during those sessions, telling Hispanic lawmakers that, as a black man, he understood what it meant for a community to feel pain.

The African American lawmakers wanted help for their constituents, too — some sort of targeted aid that might lift ailing black communities. Except they felt more constrained than their Hispanic colleagues.

So they crafted a proposal, written largely by Rep. James E. Clyburn (D-S.C.), to send 10 percent of economic recovery funds to communities in which 20 percent of the population had been under the federal poverty level for at least 30 years. It was an idea that could benefit a number of rural white districts in Republican states but that also would clearly benefit urban black communities, and the lawmakers believed its bipartisan appeal would make the proposal a comfortable sell for Obama.

In April, a group of five caucus members, led by Cleaver, took the plan to the Oval Office. They laid it out for Obama, carefully avoiding any references to how it might help blacks in particular.

“With this plan, we explained to the president, ‘nobody could say you’re just trying to do something that’s exclusively to help African Americans,’ ” Cleaver recounted.

“We did not want anybody ever to say the president was plotting with the CBC to have discriminatory legislation,” Cleaver added. “We didn’t want to put him in that position.”

A narrow version of the measure regarding agriculture funds had been included in Obama’s 2009 stimulus package. The administration regularly points to an array of policies it has proposed and enacted over the years to help struggling communities, including some initially drafted by Black Caucus members, though it has not pushed the 10-20-30 plan more broadly in its jobs proposals.

‘If not now, when?’

One thing still bothered Cleaver. By the end of 2011, more than two years into Obama’s tenure, the first black president had yet to meet with the country’s most prominent black businessman.

Robert L. Johnson, the billionaire founder of Black Entertainment Television, had fiercely supported Hillary Rodham Clinton over Obama in the 2008 primary. Neither he nor the White House had tried to forge a relationship. Johnson at one point in 2011 had used a “Fox News Sunday” appearance to warn that Obama should “recalibrate his message” away from targeting corporate jet owners and other wealthy Americans for higher taxes. Later, he said that African American communities were not getting the help they needed at a time when the black jobless rate exceeded 14 percent.

“It’s not good for history, it’s not good for our progeny, that a person of Bob Johnson’s accomplishments and stature did not have the best of relations with the first black president,” Cleaver said. “It doesn’t smell good when you’re eating Thanksgiving dinner in 2035 and you’re talking about the Obama years. All African Americans would want that relationship to be stronger.”

So Cleaver orchestrated a meeting, in December in the Roosevelt Room, between Obama and Johnson, along with about a dozen other black business leaders.

Johnson understood Obama’s dilemma. He wanted to ask the president to do more for his fellow blacks, but how could he bring it up? The question for blacks, he said later, was, “How do we maneuver to get those things on his agenda without setting a political trap that others will try to push him into?”

The pride that African Americans have felt about having one of their own in the White House would be crushed if Obama were to lose in November. Yet, they have watched as Obama has rewarded other core constituencies with favorable policies. What if a black president cannot deliver for blacks? Johnson said he believed Obama’s legacy should be that he took direct action to close the gap between black and white unemployment.

“If not now, when?” Johnson asked. “If not Obama, then who?”

Johnson came to his meeting armed with a proposal — that Obama ask the business executives and others on his jobs council to consider endorsing a plan to encourage corporations to hire more minority managers and executives. He wanted a recommendation from the White House that companies adopt an across-the-board policy to interview at least one minority candidate for any managerial vacancy. He called it the “RLJ Rule,” and it was based on a practice adopted by the National Football League when teams recruit new coaches and general managers.

Obama said he liked the idea and offered to bring it to his jobs council, a panel tasked with recommending ideas for increasing employment. Johnson said he held follow-up meetings with White House staff but that nothing ever came of the idea.

Four months later, at an April fundraiser at the home of former Democratic national chairman Terry McAuliffe, Johnson requested a few minutes alone with the president. He reminded Obama of his proposal.

The president smiled, according to Johnson, but offered only a hint that Johnson’s idea might get traction. First, the president said, he needed Johnson’s help to win reelection. Then, he added, he would look forward to working with him in a second term.

Johnson said he is willing to wait. As he sees it, strong turnout from African Americans will seal Obama’s victory, but then he expects a two-year focus by a reelected president to boost black communities.

Now, just a week of campaigning remains. The race is tight, and Obama has his hands full. The first black president is trying to extend history.

Alice Crites contributed to this report.