Emanuel Cleaver, a Missouri congressman and former head of the Congressional Black Caucus, remembers one first-term meeting during which caucus members appealed to Obama to seek funds for a programme to reduce unemployment among black youth.
The president's response reflected his governing style: He said he'd advocate for a programme for all youth.
It's consistent with how Obama has always described himself – the first black president, not the president of black America.
Dyson once noted Obama's preference for a universal approach, pointing to something the president told him in a 2010 interview: "I've got to look out for all Americans and do things based on what will help people across the board ..."
Qwanchaize Edwards, who grew up in Altgeld Gardens, says he initially hoped Obama's community organising past would spur him to pursue the kind of Great Society social programs enacted by President Lyndon Johnson. But he understands why that was impossible.
Some people will say Obama "knows the South Side of Chicago. He knows poverty. He should have done more," says Edwards.
"But I think if you look at...all the factions that he had to deal with, he probably got as much as he could get done. So he didn't do enough for poverty, but I don't blame him."
Obama faced a solid wall of GOP resistance to much of his agenda, although some question whether the opposition was strictly ideological. Lorenzo Morris, a Howard University professor, notes some Republicans publicly announced they'd oppose his programs even if they agreed with them.
"So if you start off with such intense hostility that if you don't call it racial, it's hard to know what to call it except stupid," he says.
"I would think it's reasonable for African-Americans to say he should have done more ... but they are still wrong because there's very little he could do. Probably the biggest mistake was if HE thought he could do more." Obama and his supporters do offer a list of accomplishments, pointing to policies they say helped all Americans and, in doing so, improved the lives of minorities.
The Affordable Care Act led to healthcare coverage for some 20 million Americans, including about four million Hispanics and three million African-Americans, according to federal statistics. However, its fate is uncertain because of Trump's vow to repeal and replace it.
On criminal justice, Obama pushed for the law that reduced disparities between mandatory crack and powder cocaine sentences that had put blacks behind bars longer than whites. And he commuted the sentences of nearly 1,200 federal inmates, almost all of whom were incarcerated for nonviolent drug crimes.
Obama focused a "very bright light on how unfair, systematically, the criminal justice system is," says Threatt, the public defender. "He doesn't need to beat a drum and say those people are there because of institutional racism...He did something about it."
The Justice Department, under Eric Holder and Loretta Lynch, also focused on civil rights violations in law enforcement, leading to agreements with 18 agencies that resulted in reforms.
Obama nominated Sonia Sotomayor, the first Latina on the US Supreme Court. And more than 100 minority judges were added to the federal bench, according to the Pew Research Center. The president also created My Brother's Keeper to expand opportunity for young boys and men of colour, a programme in some 250 communities.
There have been disappointments, as well.
The House refused to consider immigration reform, and so Obama used his executive power to temporarily halt the deportation of 1.5 million people brought here illegally as children. A lawsuit prevented him from expanding that to others.
Says Gaby Castillo, an immigration lawyer in New York: "I had these unrealistic expectations that all these changes would come and there would be no opposition to it and it was going to be this glorious initial first four years."
Others point to the yawning income gap that has left some African-Americans at the bottom of the economic ladder.
Author Ta-Nehisi Coates argued in a 2013 piece in The Atlantic that the Obama administration wasn't aggressive enough in dealing with the foreclosure crisis, which devastated African-Americans. He characterised the president's work on housing segregation as "run of the mill."
Harris, the professor at Columbia University, says Obama didn't sufficiently address the persistence of racial inequality and championed the causes of other key constituencies, such as the LGBT community, more than African-Americans.
"In eight years," he asks, "this is the best you can do?"
For Obama, just talking about race has always meant walking a rhetorical tightrope. He's been criticised as too strident and too timid, too slow to react and too fast to make a judgment.
Some white critics accused the president of taking sides when he said Trayvon Martin, the black teen killed by a neighborhood watch volunteer, could have been his son. Some black activists insist Obama should have been more outspoken in denouncing police killings of African-Americans in Ferguson, Missouri, and elsewhere.
"On one hand," says Cleaver, "the president is suffering from inflated expectations on the part of African-Americans. On the other side, you have people who have a magnifying glass out looking for a statement ... that would allow them to say he's a card-carrying member of the Black Panther Party."
Cleaver says Obama's style has always been calm and deliberative. He's the "most careful African-American in a leadership position that I've ever been around."
Dyson argued in his New York Times op-ed that Obama's reluctance to address race had significant political ramifications. If Obama "had spoken more forcefully on race," he wrote, "it might have blunted some of the bigotry" that helped to fuel Trump's ascent.
In recent years, as tensions worsened between law enforcement and communities of colour, the president grew more vocal but still tried to strike a balance when addressing racial conflict. At a memorial for five slain Dallas police officers last summer, he noted the fears many African-Americans have of law enforcement – but also the dangers officers routinely face at work.
"We wonder if an African-American community that feels unfairly targeted by police and police departments that feel unfairly maligned for doing their jobs can even understand each other's experiences," he said.
That kind of message doesn't satisfy Constance Malcolm, a Jamaican immigrant who supported Obama in 2008. Her frustration has deeply personal roots.
Her 18-year-old son, Ramarley Graham, was fatally shot by a New York City police officer in 2012 in the bathroom of her apartment. Police had followed Graham, thinking he was armed. He was killed when he tried to flush some marijuana down the toilet. The officer, who was not prosecuted, said he thought Graham was reaching for a gun.
Malcolm says she had hoped Obama would have been bolder in addressing police treatment of young black men. "I understand sometimes it's a political thing," she says, "but sometimes you have to break that barrier and speak up about what's going on."
Alicia Garza, co-founder of Black Lives Matter, also thinks Obama has been more inclined to preach consensus rather than highlight injustice.
His approach, she says, has been: "Let's bring all sides together ... this is still the greatest country in the world, and ultimately cooler heads need to prevail so that we can come to a solution.
"What's really disappointing and frustrating ... is that it essentially assumes that there is an even and level playing field between black communities and law enforcement."
Eight years ago, it seemed America had turned the page – a black president in a nation scarred by slavery and Jim Crow. The euphoria was measured in public opinion; a New York Times/CBS News poll in April 2009 found 66 per cent of Americans regarded race relations as generally good.
Last summer, that poll found 69 per cent of Americans believed race relations were mostly bad.
That dramatic turnaround followed a year beset by racially charged incidents, including the death of Freddie Gray in Baltimore while in police custody and the massacre of nine black worshippers by a white man at a South Carolina church.
Recent surveys have shown huge gaps in how blacks and whites view race. In a June poll by the Pew Research Center, nearly 9 in 10 blacks – 88 per cent – said the nation needed to continue making changes for blacks to have equal rights with whites. For whites, that number was substantially lower: 53 per cent.
The divide was even starker when it came to Obama.
About 51 per cent of blacks said Obama had made progress toward improving race relations, compared with 28 per cent of whites. The poll also found 32 per cent of whites blamed Obama for making race relations worse, compared with 5 per cent for blacks.
In his final weeks in office, Obama addressed racism, maintaining in a CNN interview that it wasn't a major component in GOP opposition to his agenda. But, he said, it was a factor for some Americans. "Are there folks whose primary concern about me has been that I seem foreign, the other? Are those who champion the 'birther' movement feeding off of bias? Absolutely," he told CNN.
Some historians believe Obama's race will ultimately matter less than his record. He'll be measured by "Obamacare," how he handled the staggering financial mess he inherited and advances in gay rights, says Princeton University historian Kevin Kruse.
That view was supported in a Pew poll last month that found 35 per cent of those surveyed believed Obama would be remembered most for his health care legislation – double those who said it would be for being the first black president.
Kruse also says Obama stayed true to his promise to be colourblind. "He really tried to be a president of all people."
In hindsight, Harris sees that as a failed strategy. "How can you be colourblind in an increasingly racially polarised nation?" he asks.
Harris says there's no simple Obama narrative. Though the 2016 vote totals were partly a repudiation of the president, he also notes Obama's approval ratings have been strong as he prepares to leave office.
"He's already made his mark," he says. "I call it the black Camelot. ... You have this wonderful black family in the White House. The dreams of generations of African-Americans have been realised.
"He was a hero to the African-American community," Harris adds. "He demonstrated leadership when there was a lot of opposition. He stood his ground, stayed the course ... and people saw him as being above the fray. That will be the lasting legacy of Obama." (AP)
Tonight, US President Barack Obama returns to Chicago, where his political career began, to give his farewell speech. President Obama will leave office with an approval rating of 57 per cent with 44 per cent saying they believed he tried to make good on his promises. One area in which his legacy will be scrutinised is race, and today, the T&T Guardian publishes the conclusion of an Assoicated Press report on the 44th US president's racial legacy.