4 Golden Moments of President Obama Being So Trill Lately


From Cuba to Bill Cosby, and then the criminal-justice system, Obama’s on something, and we’re loving it.

By Diana Ozemebhoya Eromosele

This article was published at The Root on July 20, 2015.

For a while there, I was concerned that President Barack Obama wouldn’t do enough to earn a think piece describing all the ways he’s kept it “completely 100″—similar to the way we commended former Attorney General Eric Holder for keeping it “eight more than 92” last year. 

Let me tell you, I fretted over this, had sleepless nights and bit my nails. I knew that the guy had it in him and shared many of the frustrations that black Americans have been hashtagging and protesting these past several months. But there’s the idea that Obama’s status as POTUS prevents him lashing out at the ridiculous ideas proposed by the GOP or speaking up about blatant injustices. Stuff like unarmed black kids getting shot in the street.

I even argued that Holder would fare better in discussions about which guy—him or Obama—was more demonstrative when it came to speaking up for black Americans. 

And then, bit by bit, almost out of nowhere, this new Obama started to appear. He’s not mincing his words or holding back, and when he does speak about controversial “race” topics, he’s forceful and speaks in a matter-of-fact way. 

Is it because he’s on his way out of office and doesn’t have as much to lose? Probably. But so what? We’re here for it, and the bottom line is this: Obama’s getting a boatload of stuff done, so it’s not as if he’s just blowing hot air. Just take a look at some of the ways he’s waved his middle finger furiously at all his haters these past several months:

Two fist pumps in the air for that blunt NAACP speech he gave on Tuesday slamming the U.S. prison-industrial complex.


He did two things very well in his recent speech at the NAACP conference: He reminded folks about the “structural inequalities” that make it harder for black and Hispanic Americans to get ahead (and I mean, he spelled them out, describing how qualified black Americans don’t get called back for job interviews or approved for housing in good neighborhoods, and how we get suspended from school at higher rates when committing transgressions similar to whites’). Plus, no one likes to talk about it, but he spoke about how slavery and Jim Crow rigged the system and put black and brown Americans at a disadvantage.

Second, he drove a needle through the prison-industrial complex by calling foul on how a lot of people are serving hefty prison sentences for soft crimes. Obama said, “We’ve also locked up more and more nonviolent drug offenders than ever before, for longer than ever before.

“And that is the real reason our prison population is so high. In far too many cases, the punishment simply does not fit the crime,” he argued.

This item appeared on Holder’s “trill” list, so it supports the argument that Holder was a mouthpiece for a lot of the things that Obama himself believed but presumably couldn’t yet say. 

He basically said, “To hell with ignoring Cuba, when’s the next shuttle boat to Havana?” 


What was great about this moment is that Obama used the ol’ “What’s the definition of insanity?” argument to justify why he felt it was high time we restored diplomatic ties with Cuba. Our policy of treating Cuba as if it didn’t exist wasn’t working, so instead of relying on our failed “embargo” strategy, he brought Cuban officials to the table to hatch a plan for the future. 

Naysayers argued that Cuban officials hadn’t done enough to garner the U.S.’ friendship, since they hadn’t moved the ball on improving human rights on the island. (As if women are allowed to drive in Saudi Arabia—but I digress.) Meanwhile, as more and more of Cuba’s history comes to the forefront, we’ll see that it was the United States that in the early part of the 20th century introduced Cubans to the racist and segregationist thinking that made life hell for black Cubans. Black Cubans were left to contend with colorism and inequality, and it was those inequaliities that made the environment ripe for Castro’s administration to come into power to attempt to undo those injustices. 

He defined “rape” in layman’s terms for those who forgot its definition just because Bill Cosby is the alleged perpetrator. 


It seemed that a few people were trying to downplay or sugarcoat what Cosby is accused of doing: giving sedatives to women he planned to sleep with. They were questioning whether his accusers consented to being drugged, and couldn’t believe that Cosby could commit such crimes.

But when court documents revealed that Cosby did have a penchant for including Quaaludes in his sexual repertoire, that made the allegations that much more substantive. Obama laid it out plain and simple for those who still weren’t convinced that this kind of behavior constitutes “rape.”

“If you give a woman, or a man, for that matter, without his or her knowledge, a drug, and then have sex with that person without consent, that’s rape. And I think this country, any civilized country, should have no tolerance for rape,” Obama said. 

He practically did the Shmoney dance in the Oval Office after hearing that his health care plan would remain intact.


Gloating is not bad all the time. Especially when you’re a guy who’s known for being level-headed and not bragging about your wins or kicking your opponents when they’re down. Then you’re allowed to gloat and boast about your accomplishments every now and then.

That’s what makes these photos of Obama reacting to how the Supreme Court voted not to gut the Affordable Care Act—known colloquially as Obamacare—that much more riveting.  

I mean, look at him giving dap to his chief of staff, Denis McDonough.


And tell me this doesn’t look like he and Vice President Joe Biden are about to start Shmoney dancing.


Here’s to many more moments of Obama speaking his mind and hopefully becoming more and more raw during his last 19 months in office. 

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The Root TV: Whose Race Legacy Will Reign Supreme: Obama’s or Holder’s?

One guy seems to be playing chess, the other checkers, and The Root staff is torn over whose strategy will fare better in the long run.

By Diana Ozemebhoya Eromosele

This video and an abridged version of this article was published at The Root on September 7, 2014.

I often wonder if President Barack Obama ought to take a page out of Attorney General Eric Holder’s book when it comes to being mindful about his legacy as the first African-American president, in the same manner that Holder seems to be astutely mindful (and adept at crafting) his own legacy as the country’s first African-American attorney general.

It seems as if one guy is playing chess (Obama) and the other checkers (Holder), and to be honest, I’m not sure which of the two is the wiser. After watching these two from a distance for the past six years, I still don’t know who I would put my money on in a poker game.

Although, I have to say that I am leaning toward Holder’s strategy—for lack of a better word.

Ever since he assumed his post as the nation’s top law enforcer six years ago, Holder has been extremely candid: here’s a list of all the times Holder demonstrated that he’s never one to mince words, particularly when it comes to the issue of race.

Then there’s Obama, the one with the “measured” approach. It seems his modus operandi has always been the long game. When people were up in arms about how Obama should have been more stern and upset when expressing anger about the shooting death of Michael Brown in Ferguson, Mo., The Root’s associate editor, David Swerdlick, reminded folks of the hierarchy that people seem to overlook: Holder gets his marching orders from Obama.

And while that pecking order is correct, I’m still concerned that Obama seems to be resting his laurels—and his legacy—on the idea that most Americans will readily get that. Or that down the road, Americans will remember. Essentially, I’m concerned that Obama is overestimating the memory of the American people by the way in which he chooses to convey his passion about issues of racial justice.

In today’s world, we ingest sound bites, memes, 15-second Vine videos and sensational photos that circulate on Twitter and Facebook. And so I suspect that in this final stretch of Obama’s administration, as people begin to form opinions about Obama’s race legacy—that is, what he’s done for black people—they’ll reminisce back to just a couple of moments: his race speech during his 2008 presidential campaign, his “If I had a son, he’d look like Trayvon” comment and, perhaps (but not likely) the My Brother’s Keeper initiative that he’s been touting of late. Yes, Obama has done a lot for black Americans (being the first black president is a major accomplishment in and of itself), but I suspect that a lot of the wonky policy stuff like Obamacare and increasing grants for students headed to college might not be on the tip of people’s tongues when they’re sitting around the kitchen table or at the barbershop waxing about “The Obama Years.”

Holder’s race catalog is, again, far more demonstrative. His we’re “a nation of cowards” speech (that reportedly caught the White House completely off guard) is pretty representative of how he has never hesitated to wag his index finger furiously at America for the way in which it has tried to sweep racism, and its symptoms, under the carpet. And then, more recently, there are those heartwarming photos of Holder doling out handshakes and hugs in Ferguson. These are the moments that will leave an indelible mark on the national conversation about race.

Holder’s got his eyes on the prize, and Obama seems to be resting assured that people will eventually recognize his influence and appreciate his approach. But knowing a thing or two about the way the collective American memory works, I’m not convinced that’ll be the case.

In The Root TV video above, I fret about Obama’s race legacy and The Root’s associate editor David Swerdlick tries to reel me back in.

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All the Times Eric Holder Kept It Completely 100

Attorney General Eric Holder

Attorney General Eric Holder

Here’s proof that our attorney general is as real as they come.

By Diana Ozemebhoya Eromosele

This article was published at The Root on July 24, 2014.

It was nothing for Attorney General Eric Holder to tell ABC News that Sarah Palin “wasn’t a particularly good vice presidential candidate” and for him to suggest, in his own way, that she ought to read the Constitution before proposing that President Barack Obama be impeached—seeing as how there would be no legal basis for such an act. Lest we forget, Holder has been speaking his mind since he got the job, and lucky for us—that is, people who love it when politicians let loose and tell us what they’re really thinking—he won’t stop.

As attorney general, Eric Holder is America’s chief law-enforcement officer. And judging by this roundup of times that he has spoken candidly and uninhibitedly about hot-button topics and controversial issues, I think it’s safe to say that Holder is the type of counsel who will give it to you straight—no chaser.

1. That time he said most of the hate and vitriol that he and the president receive stems from racism.

President Barack Obama and Attorney General Eric Holder

President Barack Obama and Attorney General Eric Holder

Holder is not saying anything that black folk and liberals haven’t been saying among themselves for years in barbershops and hair salons, at the kitchen table and on MSNBC. Let’s face it: President Barack Obama could bring unemployment down to 3 percent, get the Dow to 20,000, make peace in the Middle East, solve the crisis between Russia and Ukraine, find that Malaysian plane, have a caramel latte once a week with Rush Limbaugh, curse Al Sharpton’s name, and he would still be hated on by some individuals who can’t stand to see an African-American president in the White House.

During an interview with ABC, Holder basically articulated that there is nothing—I repeat, nothing—that the president could do to win over those people who can’t wrap their minds around there being a black president. These bigots hide behind their half-baked political arguments and trot out played-out talking points from the 1980s to mask their utter disgust of what Obama represents: an H-N-I-C.

2. That time he begged David Simon to bring back The Wire.

holder and the wire _2

Attorney General Eric Holder; Idris Elba and Wood Harris in The Wire

We knew that Obama’s presidency was going to be a truly special experience when he gushed about how much he loved The Wire—the critically acclaimed HBO show. We black people practically stomped our feet, cupped our mouths and mouthed “Yooooo!” when Obama said that Omar, the gay stickup bandit played by Michael K. Williams, was his favorite character.

But Holder one-upped his boss during a panel discussion when he pleaded for David Simon, the show’s creator and lead writer, to bring back the series for a sixth season. The attorney general, like the rest of the show’s cultlike following, knew how authentic the series was in communicating the complexities of inner-city life: There are no good or bad characters in the hood. Nearly everyone—the cops included—is shades of gray.

3. That time he told those Republicans who were hell-bent on perpetuating the Fast and Furious scandal to get a life.


Attorney General Eric Holder

It was a well-intentioned strategy of follow-the-gun-trail. Federal agencies looked the other way while American guns were being sold up the ladder to high-level drug-cartel leaders in Mexico. The plan was that U.S. law-enforcement officials would monitor the gun sales to eventually catch all of the big-time criminals wreaking havoc in and around the border.

That was until some of the guns were found at the murder site of a U.S. border-patrol agent. Somebody needed to take the fall for Operation Fast and Furious, and the GOP picked Eric Holder. He became the only Cabinet member in U.S. history to be held in contempt of Congress. The attorney general didn’t take too kindly to what he perceived was election-year shucking and jiving by Republicans, and described the entire ordeal as “truly absurd conspiracy theories” that were “unnecessary and unwarranted.”

It’s his politically correct way of saying, “This is bulls–t.”

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