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We Are the Leaders, Issue #17, Rev. Jesse L. Jackson Sr.

by BREAKTHRU Team

February 27th, 2026

Dear Leaders,

This past week, as news of Rev. Jesse L. Jackson Sr.’s passing spread, the images came quickly through my social channels. Grainy convention footage. His enduring slogan, “Keep hope alive.” A younger Jackson, arm in arm with civil rights leaders. Photos that now feel like the prologue to another chapter: the one that would make space for Barack Obama and so many others who followed.

As I took a closer look at his life, what struck me was that long before inclusion was broadly marketable, Jackson was inviting those pushed to the margins into his Rainbow Coalition — including LGBTQ+ Americans at a time when doing so carried real political risk. He spoke of the rainbow not as metaphor alone, but as a mandate: if it is not wide enough to hold all of us, it is not worthy of the name.

In 1988, standing before the Democratic National Convention, he said plainly:

“I am not a perfect servant. I am a public servant. I stand for equal protection under the law for all Americans — including gays and lesbians.”

Remember, this was 1988. The height of the AIDS crisis.

He carried that message into unexpected places, from presidential stages to Sesame Street, signaling to children of all backgrounds that they, too, belonged in the American story.

And at the very moment those images were circulating — of a coalition builder expanding the definition of “us” — another cultural moment unfolded. Our men’s Olympic-winning hockey team laughed in a locker room at misogynistic language that reduced women to punchlines. The laughter was followed not by silence, but by minimization. By explanations. By attempts to brush it off and make the controversy disappear.

Meanwhile, in an irony no one could script, Flavor Flav, the oversized clock-wearing hype man of Public Enemy, born William Jonathan Drayton Jr., raised in Freeport, Long Island, a classically trained pianist who grew up in church before becoming one of hip-hop’s most recognizable voices was publicly stepping forward in defense of women athletes. Here he was, using his platform not for spectacle, but for support. It is a striking juxtaposition, who speaks, who deflects, who expands the circle, and who protects the comfort of the existing one.

I imagine Jesse Jackson would be proud of Flavor Flav, and would challenge others to follow his lead.

This Week’s Reflection: Rev. Jesse L. Jackson Sr.

Jesse Jackson was born in 1941 in Greenville, South Carolina, into the architecture of segregation. He was born to a 16-year-old mother, Helen Burns, a domestic worker, and grew up knowing both the instability and stigma that came with being the child of a teenage, unmarried parent in the Jim Crow South. His stepfather, Charles Henry Jackson, adopted him and gave him his surname, but the tension around his birth and identity marked his early years.

He came of age in a country that made its hierarchies explicit and enforced them without apology. Greenville was rigidly segregated (schools, neighborhoods, public spaces) and Jackson grew up navigating both the constraints of racism and the expectations placed on young Black boys to stay in their place. At the same time, he was a gifted student and athlete. He excelled in football and baseball, earning recognition that gave him glimpses of opportunity beyond South Carolina. But talent did not insulate him from exclusion. He understood early that achievement did not erase discrimination; it simply made you more visible within it.

After graduating from high school, he attended the University of Illinois on a football scholarship before transferring to North Carolina A&T, a historically Black college where his political consciousness deepened. It was there that he became involved in the sit-in movement and civil rights organizing.

As a young man, he joined the civil rights movement more formally and worked alongside Dr. Martin Luther King Jr., eventually becoming a national figure within the Southern Christian Leadership Conference. He was present in Memphis in 1968 when King was assassinated — a moment that would shape the rest of his life and leadership.

He did not step away from public life after tragedy. He stepped further into it.

Through Operation PUSH and later the Rainbow Coalition, Jackson focused not only on protest but on participation, which included working on voter registration, economic access, and political representation. He believed dignity required structure. It required presence at the tables where decisions were made.

And so in 1984, he ran for president. It is difficult to convey what that meant in that moment. A Black candidate mounting a serious national campaign was widely dismissed as symbolic. But, he ran to win.

By 1988, he had won 13 primaries and caucuses and finished second in the delegate count. He expanded the electorate across the South. He reshaped the Democratic Party’s platform. He proved that “viable” is often a word used to guard existing power. He ran before the country believed someone like him could win. And in doing so, he widened the road for those who would follow. (For a deeper look, I recommend: A Dream Deferred: Jesse Jackson and the Fight for Black Political Power.)

I looked at his 1988 Democratic Convention speech through the lens of Leadership Types. Jackson most clearly embodied the Champion. The Champion’s core motivation is dignity-centered inclusion. Not unity for optics, but unity rooted in moral conviction. When he declared: “When I look out at this convention, I see the face of America — red, yellow, brown, black and white — we’re all precious in God’s sight,” he was expanding who counted.

Champions lead with compassion, resilience, and principled courage. They unite diverse communities through hopeful, morally anchored language. But that kind of visibility raises the bar and exposes the leader to greater scrutiny.

Expanding the circle does not make someone flawless. In fact, visibility often does the opposite. When you stand at the center of attention, your mistakes are amplified. Jackson experienced that.

After his 1984 “Hymietown” remark (a slur referring to Jewish people) became public, the backlash was swift and severe. It threatened the very coalition he was trying to build. He did not dismiss it as media distortion. He did not double down. He publicly apologized, repeatedly and directly, acknowledging the harm of the language. But more importantly, he did not treat the apology as a press cycle event.

He met with Jewish leaders. He sat in rooms that were uncomfortable. He visited synagogues. He strengthened relationships with longstanding Jewish civil rights allies. Over time, he became an outspoken opponent of antisemitism and worked to repair trust within the communities he had hurt.

Repair, in his case, was relational. It was sustained. It required proximity.

It is a good reminder that Leadership is not the absence of imperfection. It is what we do when imperfection is revealed.

Why This Matters Now

Back to this week: the headlines and the scroll of our social media feeds. We all know the “locker room moment” was not about one joke. It was about power. It was about culture. It surfaced as a misogynistic reflex, what we have come to euphemistically call “locker room talk.” The kind of language that reduces women to punchlines and sidelines. The kind of laughter that signals belonging for some by diminishing others. The kind of shorthand that excuses itself as harmless, competitive, “just how guys talk,” while quietly reinforcing sexism, patriarchy, and exclusion.

It was also something many of us have experienced before.

What followed, the quick pivot to minimization, the insistence that it was overblown, the attempt to smooth it away, revealed something deeper than the joke itself. It revealed how instinctively dominant culture protects itself.

When the video surfaced, there was visibility. There was a clear opportunity for accountability, a moment to say plainly, “We were wrong.” Instead, much of the effort went toward containment. Toward finding explanations. Toward elevating women as surrogates to soften the blow, a player’s mom, former female hockey players issuing statements about how great the guys are. I saw many of those responses, gestures designed less to confront harm and more to quiet it.

Minimization is a form of maintenance. It preserves the circle as it is.

That is why the juxtaposition this week, archival footage of a leader who expanded the circle alongside contemporary efforts to shrink controversy back into comfort, feels instructive.

Expanding the circle is not abstract work. It happens in locker rooms and boardrooms, in group texts and offhand comments, in whether we correct, apologize, or look away.

From Reflection to Action

At BREAKTHRU, we often say that identity is strength, not something to hide, but something to lead with. But that belief only holds if we are also willing to protect the identities of others, especially when doing so costs us comfort. So the reflection is not only about systems. It is about ourselves.

This is where the tension lives. Ask yourself:

Where am I protecting the comfort of the room instead of the dignity of someone within it? 

Where does fear of losing belonging stop me from widening the circle?

Jackson knew it too and he made mistakes along the way. But because he tried, the circle widened.

The leaders who shape history are not the ones who preserve the circle exactly as they found it. They are the ones who stretch it.

Until Next Week

 

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We Are the Leaders, Issue #16, Grace Lee Boggs