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Why I Backed Hillary…Over Obama.

by | Feb 28, 2020

I never expected to see a Black President in my lifetime. One of the few pictures my Mom had hanging from the wall in our living room was of Malcolm X. I don’t recall us ever discussing him, or his contribution to our story of Black America. It was just his face, staring straight ahead, looking determined. There was no written saying on the picture like “By Any Means Necessary,” but that picture didn’t need it. His expression said it all.

I didn’t learn much about him when I was in Public School that I can recall. But I was fortunate enough to attend a private school on scholarship: The Dalton School, attended by the rich, famous, and soon-to-be famous – Anderson Cooper graciously welcomed me to the school upon my arrival, as he was in the grade above me and served as a member of student government. Tracee Ellis-Ross was a few grades below me, one of a handful of black students I noticed because, well, how could I not? There were so few of us.

In history class, I remember spending one full week on Black History, and that’s when I first learned about Malcolm X. My takeaway from that lesson was that he advocated violence, and called the white man a “blond-haired, blue-eyed devil.” That was IT. While those things were true, it was only PART of his story, and that kind of robbed me from learning of his full journey, and robbed me of a potential Black hero to look up to.

Dr. Martin Luther King Jr fared much better in how HIS story was told, as his non-violent message was safe and unthreatening enough to disseminate unfiltered. The song “We Shall Overcome” and his famous “I Have A Dream” speech were approved to be doled out as shorthand for “He’s one of the good ones.”


While I loved Dr. King’s uplifting speech, telling of a day when people would not be judged by the color of their skin, but by the content of their character, I was more inclined to believe the comic cynicism of one of Eddie Murphy’s stand-up bits.

Wearing a bright red leather suit during a stand-up special in Washington DC, he joked about how the Rev. Jesse Jackson (who was running for President at the time) had been working out and, specifically, doing a LOT of running. He said he asked him “why the fuck you getting in shape like this?” And he said Jesse told him “‘Cause Imma be the first Black President. Imma have to give speeches like this —” (running back and forth): 
“My fellow Americans (running)…
as your President I feel…(more running)…
that we as a people must join hands…(more running)…
“Are you watching these mothafuckers back there? Cause I don’t think they too happy about this shit!”

Sure, I laughed heartily as Eddie pretended to be Jesse Jackson, running back and forth across the stage to keep an imaginary sniper’s scope off of him, but the image stayed with me, burned into the retina of my psyche like staring at the sun too long. In MY mind, America would NEVER elect a Black President. NEVER.

Now, of course, this didn’t stop me from being optimistic about Rev. Jackson’s chances, that is until his anti-semitic remarks calling New York “Hymietown” all but buried his campaign. Being a young twenty-something at the time, my rose-tinted glasses were still brimming with hope. I used my first vote as an adult to help elect David Dinkins as the first Black Mayor of New York City. But a racially-charged incident in Crown Heights put an end to his mayoralty after just one term. I still had hope, though.


That hope was smashed to smithereens, however, after 2 presidential terms of the worst President I had ever seen at the time – George W. Bush had somehow won the election in 2000 without winning the popular vote, and then he won AGAIN by defeating John Kerry, a highly-intelligent, decorated war veteran, in 2004. This was AFTER Dubya got us involved in a long and costly war based on a lie. 

At that year’s Democratic National Convention, a young Senator named Barack Hussein Obama gave a speech that had many pundits declaring him an up-and-coming political figure to watch. Yep, I thought he gave a great speech and all, but I didn’t think he had a snowball’s chance in hell at being elected President.

Let’s put aside his sparse political experience for a minute. The man’s middle name was HUSSEIN. We had just started a war looking to end the life of the Iraqi leader by the same name. And then, let’s talk about the rest of his deal. He’s a Black man. With the name Barack Obama. Having been an avid consumer of comedy and parody for my entire life, my brain queued up images of him wearing kinte cloth, with a bone necklace hanging around his neck, and other “Coming To America” jokes.

It’s not that I personally saw him this way, no sir. In fact, it made me SUPER proud that this man was so highly regarded by the media and the general public. People often spoke about him the way I had become accustomed to hearing myself spoken about: “Oh, he’s so articulate and well spoken. Very well-educated,” as if that was not to be expected of people who looked like us. 

I’m giving MOST of the folks who gave me “compliments” like that a pass, because I am 100% sure that they weren’t meant in malice; they believed that they were being kind by commending us for having been able to avoid speaking “Ebonically,” as was so customary amongst other folks of our race. It was still, unintentionally or not, a backhanded compliment, like “Hey, that black shirt makes you look way thinner,” or “You’re a good driver for a woman.” In any case, it IS true about President Obama: He is one of the most gifted orators I have ever seen, regardless of race.

But I had seen my fair share of racism here in America, and I didn’t think a Harvard-educated, articulate, suave and sophisticated Black man named Barack Hussein Obama would be able to convince a country filled with racists that HE was the man they should entrust to lead the nation. 


Around this time, a lot of folks were steadily trying to push this narrative that America was now “post-racial,” and that racism was no longer an issue. My Black ass, being passed by taxicabs on the street (while wearing a business suit) only to see them stop mere yards past me to pick up a White passenger, would beg to differ. As a grown-ass, hard-working, taxpaying man with 3 children, I was STILL being watched suspiciously in department stores, as though I couldn’t WAIT to rip off some of their merchandise and use the money to buy and sell drugs. When you’ve spent your entire life being Black, you know what those looks are.

So, as cool and trendy as it seemed that Obama was running for President, I decided the smart money should back Senator Hillary Clinton. Although she was a polarizing figure who had been attacked by the GOP for decades, she seemed far more experienced, she had had-profile name recognition, I felt like I knew her (she was our Senator, after all), she was battle-tested, and yes, she was White. As it turned out, that advantage wasn’t much of an advantage at all, because she was still a Woman, and the nation wasn’t ready for THAT shit yet.

I had spent so many years with that Eddie Murphy routine languishing in my comedy memory, it had taken hold as FACT in my head: America would NEVER elect a Black President. And, if they did, he would most assuredly be assassinated shortly thereafter. So I was wrong on BOTH counts.

But I still didn’t know it yet. I was busy telling people “Ah, he’ll never win. I’m supporting Hillary, she has a MUCH better shot at being elected. Why waste a vote on a guy who will never win?” Wrong. Wrong. Wrong.

And THAT is the point of this long-winded piece. Despite my decades of personal experience, and data collected from any number of historical sources to confirm my fears/beliefs, I did NOT have a crystal ball. Nobody does. And, once Obama had won the Democratic nomination, I became one of his BIGGEST fans, and never looked back. To this day, he is STILL in my humble opinion, the best President of my lifetime.


But he was a once-in-a-generation talent. We won’t see another one like him for a long time. But what we DO see right now is a similar moment in history: with so many choices to choose from to unseat the most unworthy, unfit, inhumane piece of shit we’ve ever seen, we are at an impasse with our fear. Our fear of making the “wrong” choice, of what the OTHER side will say about him/her, is unfounded.

They had PLENTY of things to choose from to throw at Obama: his race, his name, his history, yadda yadda yadda. But he still won, because enough people collectively decided to do the right thing. What we are witnessing is a phenomenon where too many people are afraid that 1. Middle America won’t vote for _____; 2. The GOP is going to attack with _____; 3. He/she isn’t electable enough to defeat trump.

Just forget about how ridiculous #3 sounds right now, because that jackass WAS unelectable, and is STILL unelectable, he just had the right Russian President to help him get in. But those other 2 items? We cannot control them. All we can control is OURSELVES, and how we converse with our fellow Americans about the choices we have.

President Obama was our FIRST Black President. We are now choosing between other firsts:

First Woman President (2 of them)
First Gay President
First Jewish President
First Democratic Socialist President
First Billionaire President – LOL, you didn’t think trump was REALLY a billionaire, did you?

And the way things are going, none of them will have to do their speeches running back and forth to avoid a sniper’s scope, because it’s likely SOMEONE will pick a Black person to be their VP, and that would make them our 2nd Black President.

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