Jesse Jackson: A Meditation On Greatness

Reflecting on the life of Reverend Jesse Jackson an icon with a mixed record

When I saw the posts on Instagram informing the world of the death of Reverend Jesse Jackson, my reaction wasn’t typical of how I usually respond when someone of his stature transitions. It wasn’t sadness, nor a sense of a void that now needs to be filled. Yet it wasn’t indifference either. As I write this, I am still searching for the words to describe my reaction to his passing.

Perhaps it’s because in recent months, public appearances by Reverend Jackson made it clear that his time on this earth was nearing an end. Or perhaps it is something more personal. Do I not value his contribution to civil rights and Black liberation as I do someone like Harry Belafonte—a man I look to as a guiding archetype for how to approach life, a connection only amplified when I learned we shared a birthday?

And yet, when I compare Jesse Jackson’s passing to that of Jimmy Carter—who was in hospice for nearly two years—there was still a distinct sense of loss when the former president died, despite his mixed record. There was something singular about both Harry and Jimmy. I don’t know if the same can be said about Jesse Jackson—but maybe that’s the point.

Jesse Jackson was arguably either thrust into the position of successor to Martin Luther King Jr., or he commandeered it, depending on who you ask. But how do you fill the shoes of a martyr? One of the greatest human beings to ever walk the earth?

Opinions about Jesse Jackson are as layered and complex as the man himself. A civil rights icon. An organizer. A presidential candidate. A builder of movements. Later in life, a diplomat and political power broker. A man who stood in the shadow of giants—and who cast a wide shadow of his own.

For many, he was a hero of the Black freedom struggle. For others—particularly on the left and among more radical elements within the Black liberation movement—he represented a painful contradiction: a figure of immense radical potential who chose to position himself within the Democratic Party establishment rather than be a force to pull the party away from the so-called political center and more to the left.

His longtime friendship with President Bill Clinton is well documented. It afforded him tremendous access to power, but at the time it also drew skepticism and suspicion from many left-leaning progressives and African American activists. In 1992, Jackson was critical of Clinton’s attack on hip-hop artist and activist Sister Souljah. The so-called “Sister Souljah moment” was a strategic calculation designed to distance Clinton from Jackson and from what some framed as “radical Blacks,” in order to pivot toward the political center. In hindsight, it served as a prelude to how the Democratic Party would often discard, attack, or sacrifice parts of its base in attempts to win over conservative, and racist voters.

Many felt Jackson’s rebuke of Clinton was not strong enough.

Later, in 2016, Jackson chose nuetrailty in the democratic primary, deciding not to endorse Bernie Sanders over Hillary Clinton, despite Sanders’ longstanding alignment with many of Jackson’s own policy positions—universal healthcare and economic equality among them. These contradictions make it difficult, at least for me and for others, to fully unpack Jackson’s legacy.

In moments like this, it is easy to reduce a life to a purity test.

I am reminded of a question made famous by another complicated and contradictory political figure, President Theodore Roosevelt: What does it mean to be in the arena?

In 1910, Roosevelt delivered a speech commonly known as “The Man in the Arena,” which included these words:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better.
The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood…”

I apply Roosevelt’s quote regularly. The kids call it “hating,” but too often we are quick to judge. Monday-morning quarterbacks, barstool analysts and internet experts are in abundance. In an era of instant commentary—social media profiles, millions of podcasters, influencers, bloggers from hobbyist to professional—it is common place to dissect public figures from a distance. And we are all guilty of it, myself included.

Of course, no one is above scrutiny or critique. Those of us committed to social and economic justice have a responsibility to examine closely those with power and influence. But we should also account for what I call the “human equation,” especially in death.

Entering the arena of Black liberation, civil rights, or leftist politics requires more than conviction. It demands courage and a willingness to sacrifice that most people simply cannot sustain.

Consider Jackson’s life. He witnessed the murder of Malcolm X and Medgar Evers—men who were his contemporaries, even if he was the junior among them. He was present when Martin Luther King Jr.—his mentor and friend—was assassinated. Before that, he bore witness to King’s constant surveillance, repression, threats, and attempts on his life, as well as the lives of those around him, including Jackson himself.

What does that do to a person’s nervous system?

Yet he remained in the arena.

Jackson went on to found Operation PUSH—People United to Save (later Serve) Humanity—emerging from Operation Breadbasket, an initiative of the Southern Christian Leadership Conference (SCLC). In 1966, King appointed Jackson to lead the Chicago chapter of Operation Breadbasket, which became a powerful coalition of Black ministers and entrepreneurs. By 1968, Jackson clashed increasingly with Reverend Ralph Abernathy, King’s successor at the SCLC. By 1971, the relationship had fractured completely. Jackson resigned, gathered his allies, and formed Operation PUSH which later merged with the National Rainbow Coalition to form the Rainbow PUSH Coalition.

Some of the distrust surrounding Jackson can be traced back to this split, as many within the movement felt compelled to choose sides. In addition, Jackson’s decision to use the name “Rainbow Coalition”—which was originally associated with a multicultural, anti-capitalist revolutionary organization formed by Fred Hampton, a member of the Black Panther Party—for a more liberal, mainstream political organization was viewed by some as opportunistic at best and exploitative at worst.

Early in his career criticized for his management style. His “rockstar”-like appeal created mistrust among some SCLC leaders, while later audits of Operation PUSH raised questions about the use of funds—operational versus personal spending, fundraising tactics, and internal accountability. These critiques followed him for decades.

His political career, too, was viewed as mixed. Left critics argued that his 1988 presidential campaign was more moderate than his 1984 run—less radical in rhetoric and more calibrated for party legitimacy. Some described it as entering the “cul-de-sac of the Democrats.”

After his insurgent bids, Jackson endorsed establishment nominees Walter Mondale and Michael Dukakis without extracting sweeping concessions. For some radicals, this confirmed their fear that the Rainbow Coalition would be absorbed rather than transform the party. Leftist and Socialist organizations described it as a warning against “liquidationism”—the dissolving of independent radical politics into a party that was ultimately coopted by the ruling class.

Then, decades later, history seemingly repeated itself,

In 2016, as Bernie Sanders mounted his insurgent campaign against Hillary Clinton the Democratic Party’s establishment choice, many saw echoes of 1984: multiracial working-class energy, anti-establishment fervor, and calls for structural transformation. Jackson did not endorse Sanders during the primary.

For some on the left, this felt like confirmation of a long trajectory: when faced with a decisive split between insurgency and establishment, Jackson chose the establishment. Critics argued that his moral authority—particularly among Black voters—might have helped Sanders close the gap in southern states early in the primary season. Some believe that had Jackson stood firmly with Sanders in 2016, the primary—and perhaps even the general election against Donald Trump—might have unfolded differently.

In 2020, Jackson did endorse Sanders. But for some, it felt late—symbolically powerful, yet strategically insufficient to rewrite the narrative of 2016.

We can and will re-litigate the 2016 election cycle as well as 2020 and 2024, but yet, we return to Roosevelt’s frame remains.

It is easy to sit in judgment from a distance, to offer alternative strategies, to say what one “should have done,” when you are not in the room—when you are not “out-front” in the public eye, inside “Roosevelt’s Arena”.

The number of plates someone like Jackson must keep spinning—staff, allies, donors, interest groups, institutional responsibilities—is enormous.

As I sit in my role as Co-Director of Democracy at Work, while moonlight by running my own media company, I understand—on a far smaller scale—the tension between vision and viability. The responsibility to people who depend on you materially. The pressure to protect institutions that provide livelihoods while staying true to the mission. There is immense responsibility and it is humbling.

So in Reverend Jackson’s case lets now multiply that pressure by decades of national and international leadership. Coupled with credible threats of violence, in addition to the burden of representing Black people, poor people, and the disenfranchised who look to you for hope.

Compromise does not always signal surrender. Sometimes it signals survival. Sometimes it signals a calculation that incremental gains are preferable to catastrophic loss.

That calculation may be wrong. It may be right. But it is made inside the arena—not from the stands.

When reflecting on a life, we can let criticism stand. We can question strategy. We can interrogate whether proximity to power corrupted him in some way. We can debate whether Jackson was a loyal servant of justice or a career opportunist.

But to what end?

The better question may be this: Over the course of his sixty-year career, did he do more good than harm? Did he help more than he hurt? Did he endeavor to leave this planet better than he found it?

Jesse Jackson expanded the political imagination of Black America. His campaigns helped pave the way for Barack Obama. For all the legitimate critiques of President Obama, his election and reelection were historically significant and a symbol to African Americans and minorities that anything is possible. Jackson registered millions to vote and helped usher into mainstream conversation policies that later fueled figures like Bernie Sanders, Alexandria Ocasio-Cortez, and Zohran Mamdani.

Had Martin not been killed that terrible day in Memphis, perhaps Jesse would have done things differently—or perhaps he would never have risen to national and international prominence at all.

As William Shakespeare wrote: “Some are born great, some achieve greatness, and some have greatness thrust upon ’em.”

Jesse Jackson was a great man—perhaps flawed, but who isn’t?

Rest in peace, Reverend Jackson.

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