Demonstrators protest in front of the police station in Ferguson, Mo., March 12, 2015, in the aftermath of the fatal police shooting of Michael Brown. 
Scott Olson/Getty Images

No one said it would be easy.

After all, what’s simple about fighting something that’s baked in the cake of American society, that constitutes its original sin?

Racism.

That’s racism with a big R and a little one. The kind that’s in your face and explicit, and the kind that you can’t grasp with your hands but seems to be in everything from where you live to where you go to school to where you work. Where your whole life seems to be guided by an invisible hand, sorting you in one pile versus another. And fighting that unseen guide is a lifelong battle, like swimming upstream with weights tied to your ankles, desperately trying to get to dry land. The weights of  subprime loans and failing schools, mass incarceration and poverty.

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It’s not easy to fight those things, and no one expected it to get any easier in the age of Obama.

“The great irony is that the age of Obama is also the great age of retrenchment in civil rights law,” says Alvin Bernard Tillery, associate professor of political science at Northwestern University.

As part of The Root’s monthly series on President Barack Obama’s last year in office, in this installment of His Lasting Legacy, we take a look at the fight for racial justice under the Obama administration. Many who have worked closely with the White House praise it for its accessibility and action even when they didn’t always agree. But Tillery, with an outsider’s eye, is a bit more critical.

The President You Want

Tillery, who says that Obama will be remembered overall as a good president, feels that his legacy on race will be one that’s long on symbolism and short on action, outlining what sounded like a Faustian bargain of black voters and the civil rights community sacrificing racial progress for high symbolism.

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“Black Americans have the President Obama that they sort of want,” Tillery says. “He’s above 92 percent approval rating [in the black community] pretty consistently. I think because black Americans have been so moved by the symbolic victory, what that means psychologically to people seeing a beautiful black first family, that they give him much more leeway on policy than they would give any other president. …

“Imagine President Bush, George W. Bush, saying he couldn’t do something for white evangelicals because it’s polarizing,” Tillery says, pointing out how under Bush, there was a debate about evolution. “[Bush] doesn’t have to do that, but he’s doing that because his evangelical-voter base wanted it.”

Tillery says that instead of being proactive on race, Obama has been “reactive,” and as to why that’s so, Tillery puts the blame back on Obama’s most loyal constituency: African-American voters.

“I know how presidents behave when their main voting bloc asks them to do something,” Tillery says. “We’re celebrating the most powerful man in the world, but [we think], ‘Oh, he’s not really powerful enough to lead on race relations, civil rights.’

“He doesn’t have to sign a[n] executive order for reparations tomorrow … but why hasn’t the president sent another Voting Rights Act to Congress? Of course it would be dead in the water, but the symbolic act of sending the bill. This is why [Democratic presidential candidates] Sen. [Bernie] Sanders and [Hillary] Clinton are running way to the left of Obama. As white politicians, they realize they won’t be given this slack by black voters in South Carolina.”

Tillery repeats a quote often attributed to the Rev. Al Sharpton, that President Obama “can’t lead a march on himself.” It was up to activists, black lawmakers and those in the civil rights community to hold Obama accountable, but, Tillery says, too many feared looking like they were attacking the man their constituents adored.

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“There’s no doubt, as an observer of the civil rights establishment, President Obama’s election destabilized traditional black politics,” Tillery says. “Politicians who would normally be out complaining about the black employment rate, complaining about there being an attack on the affirmative action mandate, calling for criminal-justice reform. … They feel like they can’t behave that way because President Obama is there. Even if they have pent-up frustration, do you want to be the left-leaning member of the black caucus leading a march against President Obama?”

Symbolism and Substance

Tillery’s view was not shared by two women who have had to work with the White House and the Department of Justice in the pursuit of equality.

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The Root spoke with the NAACP Legal Defense and Educational Fund’s Sherrilyn Ifill and the Advancement Project’s Judith Browne Dianis about what it has been like to push for racial justice in the Obama era. Both spoke favorably of the president, with Dianis giving Obama a “B-plus” on race and crediting his administration with being more accessible and understanding than previous administrations, even if they didn’t always agree. And Ifill heavily praised the president for the appointment of former Attorney General Eric Holder, crediting Holder, under the direction of Obama, with restoring the Civil Rights Division of the Justice Department, which had suffered under the previous Bush administration, and for acting on the voter-suppression laws that swept the nation shortly after his election.

“He has definitely moved issues of racial discrimination, racism and the discourse around race in ways that we haven’t seen before,” Dianis says. “Of course, there’s the symbolism of the first black president, but he has also had those moments where he’s had a conversation about race with Americans. That has been very important for him to be able to use his bully pulpit to talk about race.”

Dianis also points to the Obama administration’s work through its My Brother’s Keeper initiative, as well as the Department of Education’s work on school discipline, as being key to resolving issues around the school-to-prison pipeline. Ifill, on the other hand, cites how quickly Holder acted on voter-ID and drug-sentencing laws, both of which disproportionately affect African Americans.

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“This, sometimes, people don’t attribute that to the president because that is an agency of the federal government, but there’s no question that he was carrying out the wishes of the president as he was setting priorities for the department,” Ifill says, adding that Holder’s actions did “reflect the views of the president.”

Ifill points out how Holder, acting on the president’s behalf, went to Ferguson, Mo., after the unrest and how young activists were invited to the White House to express their concerns directly. Both Ifill and Dianis say the Obama administration has often worked behind the scenes on issues that affect African Americans, with Ifill adding that some of Obama’s best work on race is often overlooked.

“These are some of the things that unfortunately people may quickly forget,” Ifill says, adding that the “last four years has been a time of intense engagement and involvement.”

Challenging the President

“Sometimes we have short memories,” Ifill says. “Because people feel [President Obama is] so accessible to them, they feel like he should say exactly what they want him to say. I always understood what that distance was, I understood what my role was.”

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Did either Dianis or Ifill ever feel that she couldn’t challenge the White House? No, both said. But Dianis did acknowledge that for others, it may have proved challenging.

“I think that not all leaders [in the black community] have been comfortable in pushing him on black issues,” Dianis says. “Because people don’t want to call him out in some regards because African Americans love their president. So some people, some groups, don’t want to be seen as coming out against the first African-American president.”

Calling out the president “has been tricky for some, but not everyone,” says Dianis, adding that younger organizations, “not having as much skin in the game,” have found it easier to push the president than perhaps some others.

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“I admire the president very much, but in the times I’ve been in meetings with him, anybody that was watching would not say I was giving him a pass,” Ifill says. “Whoever is the president, it’s my job to question the president. Pushing him further on … I never felt it was my obligation to soft-pedal.”

“I do know that many people have been disappointed, and [there are] times that I’ve been disappointed,” she says, “but it would shock me, leading a major civil rights organization, [that we would be] going lockstep.”

Ifill’s occasional disappointment in some ways mirrors that of black America’s own ins and outs with the president, all the while still supporting him ardently. Just before this year’s State of the Union, many expressed hope that Obama would cut loose and speak candidly on race. In fact, race largely went unmentioned, although he did quote Martin Luther King Jr. by saying, “Unarmed truth and unconditional love will have the final word.”

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Ultimately, history will have the final word on how President Obama truly fares on race in America. With much work still to be done and so many rivers still to cross on civil rights, how Obama will measure out—as stalwart champion or stymied cipher—is yet to be told, but likely will end up somewhere in between.

Also in the His Lasting Legacy series:

Historic Presidency, Historic Opposition: The Legacy of President Barack Obama

The Deadening of Blackness in the Age of Obama