What Do Obama, Trump, and Michael Jordan All Have in Common?

A Political Journey From Coast to Coast.


bout 12 years ago, on one crisp evening in The Windy City, a Chicagoan gave a speech to a crowd of more than 200,000 adoring onlookers. They had all nestled into Chicago’s Grant Park, a sprawling green expanse buttressed against Lake Michigan, home to some of the city’s finest adornments. The park, named in honor of Ulysses S. Grant — the Union Army Civil War general and 18th president of the United States — served as the venue for the soon to be 44th president of the United States. The huddled masses gathered on the Chicago lakefront to hear the first presidential acceptance speech delivered by an African-American, Barack Hussein Obama.

The impact of Obama’s speech, quite literally, hit a little closer to home for me as I was Chicago born and bred, and Black-American, three generations removed from the Great Migration up north. Here was this Southsider (that’s Chicago-speak for White Sox fan) who, while not being native to the city, had nevertheless, lived in Chicago long enough to know what condiments to apply to a hotdog, introducing himself to the world from our home city.

There was something irresistibly poetic about witnessing the nation’s first African-American elected to the presidency, delivering his acceptance speech in a venue named after the general who defeated and accepted the surrender of an army fighting to uphold chattel slavery of African-Americans.

President-elect Obama’s speech opened with:

“If there is anyone out there who still doubts that America is a place where all things are possible, who still wonders if the dream of our founders is alive in our time, who still questions the power of our democracy, tonight is your answer.”

Obama’s cadence was as soothing as music, his words majestic, his calmness exuding the reassurance an ailing country so desperately needed, and I…well, I wish I had been there to see it in person.

A little more than 6 miles further south, while Obama was delivering this once in a lifetime where-were-you-when it happened speech, I was in graduate school, in a classroom at The University of Chicago thinking to myself, “Why the hell am I in this class right now and not at Grant Park?” Pure and utter lameness was my answer.

For those whose eyes were affixed onto then President-elect Obama, the answer, summed up in one word, was hope.

My regrettably studious decision lies adjacent to another Chicagoland regret. As a kid, my eyes were affixed to the television every time the Chicago Bulls took to the court. Growing up, I watched Michael Jordan, the greatest of all time, deliver clutch victory after clutch victory for his faithful fans. Having spent my childhood watching greatness year after year, it was only until after Jordan’s departure from the Bulls that I realized I’d missed my opportunity to see Air Jordan play live and in person.

So there I was, a year removed from undergrad, unable to find a job, resigned to moving back in with my parents — not even my parent’s basement but my actual childhood bedroom — returning to school to improve my job prospects during a burgeoning financial crisis. There in that classroom, I came to grips with the fact that not only had I missed my opportunity to see Jordan play in person, but also the chance to see Obama deliver his momentous acceptance speech to the world. Leave it to me to find a way to Trump one lame decision with another.

That historic Grant Park acceptance speech marked the end of the tumultuous eight years of the Bush-Cheney administration. In response to the terrorist attacks on 9/11, the George Walker Bush presidency — considered by many to be the Dick Cheney presidency — engaged in a brand of Orwellian doublespeak, idiosyncratic to their administration. Kidnapping and torture were legally codified and rebranded as “extraordinary rendition” and “enhanced interrogation.” The Bush Doctrine facilitated the use of preemptive war to justify any military action the U.S. saw fit, including the invasion and occupation of sovereign nations on false premises. It was my freshman year of college, in my dorm room, when I watched the opening of Operation Shock and Awe and saw the first bombs fall on Baghdad.

By 2008 thousands of American troops had been killed in action, tens of thousands more maimed, hundreds of thousands of Iraqi civilians had lost their lives, and neither of the wars in Iraq or Afghanistan had an observable end in sight. Not to mention the indifference and inaction demonstrated by the Bush-Cheney administration towards the predominantly black and working-class city of New Orleans, left to drown after Hurricane Katrina flooded the city. Serving as an encore for their neo-conservative administration was a financial catastrophe that would sink the industrialized world into a recession and cost millions of Americans their jobs, retirements, and homes.

That financial calamity was the only reason I returned to school in the first place. After having moonlit as a substitute teacher and library assistant, my primary occupation of looking for full-time employment had not borne any fruit. Even in such circumstances, my station was far better than the millions of families struggling to keep a roof over their heads.

The sky was falling, and the 2008 presidential election would decide if America would climb out of the hole it had dug itself. The election of the country’s first black president, a man born of a Kenyan father and white mother in Hawaii, with the middle name Hussein no less, would be our savior. He would pull us back from the brink, restore the nation’s credibility on the world stage, and return eloquence, decency, and dignity to 1600 Pennsylvania Avenue. Obama’s victorious election was the first step for a nation in desperate need of recovery.

Entering the White House with the most severe financial collapse since The Great Depression and two unresolved wars, the Obama administration would have their work cut out for them. The U.S economy was retracting as unemployment was reaching post-Great Depression highs. Speaking to the Grant Park crowd and the entire country, Obama proclaimed to all that he understood everyone needed help at such a precarious time.

“Let us remember that, if this financial crisis taught us anything, it’s that we cannot have a thriving Wall Street while Main Street suffers.”

Towards the end of Obama’s tenure, unemployment had dropped to pre-Great Recession levels, down to nearly 4.5%. The U.S. economy had not only rebounded but had reached all new heights by the end of Obama’s two terms. The former community organizer from Chicago managed to lead a recovery that marshaled a return to the economic prosperity the U.S. was known for.

And then Trump happened.

Watching the election coverage that night with my girlfriend, Shock and Awe written all over my face as the networks called state after state for Donald John Trump, I turned to my girlfriend and said, “You gotta be sh!ting me!

Utter and complete disbelief reverberated throughout the media, the political establishment, and metropolitan hubs all across the U.S. The question everyone was pondering was how the nation could elect such a bombastic, virulent, reality T.V. host and real estate mogul with the propensity to turn dog whistles into air horns to the presidency? Trump, against all prognostications, managed one of the greatest political upsets in presidential electoral history, defeating former first lady, senator of New York, Secretary of State, and political juggernaut Hillary Rodham Clinton.

After such a bountiful recovery stewarded by an eloquent and magisterial statesman such as President Obama, how on earth could America elect a celebrity, famous — as well infamous for other accolades — for doubting his predecessor’s citizenship?

Well, depending on where you fell in the class hierarchy of the U.S., your financial recovery was either healthy and robust or entirely nonexistent. With a lifeline of hundreds of billions of dollars thrown to the very same perpetrators of the economic meltdown, the stock market came roaring back. If you were a member of that segment of society with assets and investments in the market, the recovery was a smashing success for you as you saw massive growth in your cumulative wealth. Even if you were like me, with no assets but armed with an advanced degree from a prestigious university, the opportunities were abundant.

To have heard Obama’s eloquent words on that historic evening in Grant park, you wouldn’t have thought the recovery would wind up leaving a large swath of America behind.

“There are mothers and fathers who will lie awake after the children fall asleep and wonder how they’ll make the mortgage or pay their doctors’ bills or save enough for their child’s college education.”

If you were one of those working-class mothers or fathers — and thereby a member of the most diverse demographic in the U.S. — the recovery did not alleviate any of your concerns. You saw the stock market soar, and the elite echelons of American society regain their wealth and then some. Meanwhile, none of this growth managed to “trickle-down” to you. If you were able to find employment, it was more than likely a low wage job earning barely enough to survive and part-time no less to save your employer from having to cover your health benefits. You witnessed the value of the only asset you were likely to own, your home, depreciate. If you were one of the 10 million families who’d lost their home, your credit was most likely ruined, making it even more challenging to acquire the necessities of life.

With recovery efforts primarily focused on big banks — the same bad actors who facilitated the economic disaster — the Obama administration failed to put in place any substantive policies that might have allowed you to stay in your home. In nearly every observable metric, during the recovery overseen and managed by the Obama administration, as the stock market grew, so did income inequality. Main Street suffered while Wall Street prospered.

With this recovery, at least in part, aimed at individuals like myself, opportunities in and around major metropolitan areas were plentiful. As such, I traded one brutal winter for another and hotdogs for lobster rolls when I moved to Boston, MA, to start a new job in tech. After a couple of years in New England, the rapidly growing and bountiful tech sector brought me to the tech capital of the world, and I traded snowy winters for the sunshine of San Francisco, CA, and lobster rolls for tacos and Thai food. The California trade was much more to my liking.

The recovery, as bright as the California sunshine for those with college educations living in and around America’s major cities, cast a very long shadow over middle America. In 2016, having been neglected by both the Republican and Democratic party establishments, the nation’s malcontents found their candidate, and millions of people who had twice voted for Obama chose to vote for Trump. Like Lady Liberty, inscribed with the famous words of poet Emma Lazarus, “…give me your tired, your poor, your huddled masses yearning to breathe free…”, was as a beacon of hope and opportunity for impoverished European immigrants decades ago, Trump was a lighting rod, representing the anger and frustrations of those left behind by Obama’s recovery. Millions flocked to Trump and his proverbial ethos of “give me your forgotten, your pissed off, your mad as hell and not going to take it anymore.

It’s not that Trump’s personality was unfamiliar to me, just that it was unfamiliar to see that in the White House. His bluster was reminiscent of drunk Chicago Cubs fans, their cups of liquid courage having runneth over after a loss (or a victory for that matter), resulting in their condition as incorrigible blowhards. Much like the inebriated “bros” stomping around Wrigleyville, Trump’s behavior while in office was marked by impulsivity, a lack of discipline, and downright incompetence. That incompetence proved costly and detrimental to the American populace, as the worst public health crisis since The Spanish Flu of 1918 engulfed the U.S earlier this year.

Having attested to the severity of COVID-19 in private, while downplaying the disease’s lethality in public, and then subsequently becoming infected himself due to negligence, the virus — as of the writing of this piece — has infected more than 10 million people in the U.S., 240,000 of which have sadly perished.

Trump’s response to the economic recession wrought by the pandemic stood in stark contrast to the populist rhetoric he campaigned on. While struggling citizens and small businesses received some temporary assistance, it was paltry compared to the aid provided to the markets, aptly described as a “money cannon” pointed at Wall Street. People like myself, equipped with advanced degrees, were able to work remotely, minimize our risk of infection, and maintain a degree of financial security during the pandemic. The same couldn’t be said of the scores of working-class folk deemed “essential.” Essential enough to keep the grocery stores stocked and Amazon packages arriving, but not enough to be provided with adequate personal protective equipment and compensated with hazard pay.

On November 7th, 2020, four days after the election had begun and after a record number of mail-in ballots had been cast, I woke up that Saturday morning, groggy and sleep-deprived, turned on the news, and saw that Trump’s presidency had finally come to an end. Anxious voters, exhausted from four years of a president who reveled in antagonizing his critics, the media, and sometimes, even the American populace, took to the streets to celebrate the end of one of America’s most peculiar and controversial presidencies.

I couldn’t help but notice a similarity to the jubilation pouring into the streets all across the country. I’d seen it before. Some twelve years prior, in my hometown, I’d witnessed (well, not in person but later on T.V.) a similar mass public display of joy and relief. Obama, on that night in Grant Park, speaking to the zeitgeist of the times, said:

“The road ahead will be long. Our climb will be steep. We may not get there in one year or even in one term. But, America, I have never been more hopeful than I am tonight that we will get there.”

At a minimum, Obama understood the severity of the challenges in 2008. His confidence comforting and resolve unwavering, this previously little known Senator from Illinois convinced a country to vote for their first African-American president. Who was I to doubt him? The feeling of relief I had after Obama’s victory was palpable.

While also feeling a sense of relief that Trump had lost, I didn’t necessarily share the feeling of elation that consumed so many. The candidates running against Trump had less than desirable records, and voters had overwhelmingly rejected them in prior contests. Before being President-elect Joseph Robinette Biden Jr, Biden had been running for his party’s nomination for 30 years, never winning a single primary, and started his 2020 primary race losing the first three Democratic primaries and caucuses. He was not successful until given the imprimatur by his former boss, Obama, and establishment kingmaker of South Carolina Democratic politics, Rep. Jim Clyburn. Vice President-elect Kamala Harris, another public figure with whom I’ve shared a city, hadn’t even managed to survive until the first contest, suspending her campaign before the Iowa caucuses.

With such less than stellar candidates, how then did the American populace manage to reward Biden and Harris with the most votes of any presidential election in history? For much the same reason so many voted for Obama in 2008, which he acknowledged that night in Grant Park when he said:

“You did it because you understand the enormity of the task that lies ahead. For even as we celebrate tonight, we know the challenges that tomorrow will bring are the greatest of our lifetime…”

This sentiment was as true then as it is now, if not more so. Regardless of the political shortcomings of Biden and Harris, the damage wrought by the pandemic was more than enough motivation for the populace to declare that they’d had enough of President Trump.

What is nevertheless disconcerting is what also received an affirming number of votes; several measures directly hostile to the interests of the working-class. In my home state of Illinois, an attempt to change the state constitution to implement a progressive tax failed, meaning that a janitor earning $30K a year will pay the same personal income tax rate as a hedge fund manager earning $1 million a year. In the state where I currently reside, California, an attempt to unfreeze commercial property taxes on properties worth more than $3 million also failed. The measure would have provided $12 billion in funding for public schools that sorely need it. Adding insult to injury, several tech companies spent a combined $200 million — the most money ever spent on a California ballot initiative — to ensure their “gig” workers would be barred from the same basic employee benefits their full-time employees, people with advanced degrees like myself, take for granted.

What might also get overlooked is how Trump managed to beat most predictions as he did back in 2016. The 2020 election wasn’t supposed to be remotely close, as most pollsters and pundits had told us that Trump would likely suffer a resounding defeat. Days had passed after ballots started being tallied, and there were still several states too close to call. More conspicuously, while Biden may have won the most votes of any presidential candidate in U.S. history, Trump won the second most. Notwithstanding an erratic presidency and bungling the response to a pandemic, roughly 9 million more people voted for Trump than had in 2016. Despite Trump’s virulent dog-whistling rhetoric, he even managed to garner the largest percentage of non-white voters of any Republican since Tricky Dick in 1960.

While it wasn’t enough to hold off Biden and Harris, Trump outperforming nearly every pundit’s and pollster’s expectation made one thing clear. America’s working-class, our essential workers, the ones who can’t Zoom into work, but who instead actually have to show up and do the work that civil society demands, are no better off now than they were before Trump took office. Long neglected and scorned, scorned for not going to college, for voting for Trump, for not voting for Clinton in 2016, or for not voting at all, they represent a constituency in the American populace that is both uniquely relied upon and taken for granted.

With the number of COVID-19 infections reaching an all-time high, the joy of the Biden-Harris victory will soon fade, and the Biden administration will be responsible for delivering something to improve the material conditions for a beleaguered working-class populace. Millions of Americans have lost their jobs and, with that, their employer-based health insurance at perhaps the most precarious of times. A good portion of the working-class — in the world’s largest economy no less — finds itself without the financial security a modern society should afford its “essential” workers. Deliver, the Biden administration must.

We surely can’t expect to live in a nation, at least not in a harmonious one, where some segments of society prosper while others flounder. Such divisions are breeding grounds for toxic polarization. Obama was most certainly concerned about such divisions on his victorious night over a decade ago when he said:

“As Lincoln said to a nation far more divided than ours, we are not enemies but friends. Though passion may have strained, it must not break our bonds of affection.”

If Biden and Harris don’t deliver, then as Trump followed Obama, what follows Biden and Harris might shatter whatever “bonds of affection” remain. Whomever it is, they won’t resemble an incompetent, impulsive, and undisciplined reality T.V. host. They’ll add polish and professionalism to the craft of harnessing the desperation and anger of America’s tired, poor, and huddled masses, and the ends to which that mass discontent is put towards, should give everyone pause. To prevent something so ominous from coming to fruition, the legacy of the Biden-Harris presidency must exceed Obama’s in delivering broad and substantive assistance to those who need it most.

I’m much older now, only a little bit wiser, and I’ve lost more than just some of the hair on my head. I’ve also lost some of my illusions. Elation, especially after elections, is fleeting. Elections have consequences and expectations. A government blind to the most vulnerable, with eyes only for the most influential — the wealthy — yields an unhealthy and unstable society.

While being relieved that 1600 Pennsylvania Avenue will have some new tenants, I didn’t share in the celebrations of my fellow San Franciscans, and this time the reason wasn’t that I was lame (or at least I don’t think so). As I mentioned before, I’d seen something similar. With the lessons of Trump’s presidency, the Obama legacy, this horrendous year, and of course, hindsight, all being 2020, I have much less regret than I used to about missing that speech in Grant Park. Never seeing Michael Jordan play a single game for the Bulls in Chicago…I’ll never live that one down.


Born and raised in Chicago, living in San Francisco, CA. Can be reached at beninbf@gmail.com, and twitter @beninbf

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