He Was Somebody: David Masciotra Remembers Jesse Jackson

00:15 - Andrew Keen: Hello everybody. It is Thursday, February the 19th, 2026. A couple of days ago, a great man died, Jesse Jackson. And everyone seems to be very sad, even Donald Trump, who acknowledged, according to CNN, the passing of quote-unquote "a good man." Jackson's biographer, one of his most distinguished biographers, is an old friend of the show, David Masciotra. He's the author of an acclaimed biography, I Am Somebody: Why Jesse Jackson Matters. David, as always, is joining us from Highland Park in Indiana. David, do you think Jackson's death—he was 84 years old—did he get to a point in his life where he wasn't offending anyone anymore? I mean, if Donald Trump is saying he’s a good man, I'm guessing that Jackson wouldn't be thrilled that Trump was saying nice things about him after his death.

01:14 - David Masciotra: Well, I'll refer to the man himself. Jesse Jackson, in one of his common alliterative, memorable phrases, once said that American culture—meaning the press, the political establishment—likes martyrs, not marchers. So, it's easy now that Reverend Jackson is deceased and that he spent the last few years of his life in poor health and pretty much off the political scene to celebrate him; but throughout his life, when he was hard at it, striving toward the full activation of democracy and the creation of a society built around social justice, he had many critics and many enemies, including some who are now casting praise upon him. So, if anything, it showcases the hypocrisy that's at the heart of American politics and journalism.

02:12 - Andrew Keen: I haven't noticed any hypocrisy these days, David.

02:18 - David Masciotra: Well, yeah...

02:19 - Andrew Keen: Well, that was a little joke. Jackson, of course, is forever associated with Martin Luther King; perhaps, at least most people think of him as the greatest, certainly modern, African American leader. When we look back, David, at Jackson's legacy, when you wrote about him in I Am Somebody, should we remember him as someone who wasn't Martin Luther King? Is it possible to talk about Jackson outside the context of King?

02:49 - David Masciotra: Yes and no. Taking it in reverse order, it's not possible to talk about him in the context of King because he was an aide to Dr. King, and Dr. King was a mentor who shaped his political philosophy and methodology in a way that was perhaps second to none. So, if you're talking about the mentality and the work that guided Jackson's life, in many ways you're talking about what he learned from the time he spent with Dr. King. But we could talk about him independent of King or anyone else because he had such a broad life of achievement, and those achievements stand on their own merit. So, for example, the graphic that you're showing on the screen—

03:41 - Andrew Keen: And just to... because not everyone's watching, David, explain that graphic. It’s the front page of a piece about Jackson in the New York Times.

03:52 - David Masciotra: Yes, and the headline is "How Jesse Jackson Took King’s Civil Rights Movement to Company Doorsteps." After King’s death, Jackson made his focus, with the organization he founded, Operation PUSH, battling against the economic apartheid of American life. So, going up against major corporations, trade unions, and lending institutions who were excluding Black Americans or imposing a pretty low glass ceiling—in addition to Latinos and others—to open up economic opportunity to those who were qualified regardless of their race. And in doing so, he secured thousands of jobs and millions of dollars in ancillary benefits for Black workers and entrepreneurs. King was actually very skeptical of that work. So, that's an example of where Jackson broke from King, but in a way still advancing King's legacy of anti-racist organization and politicking.

05:07 - Andrew Keen: David, does that fit into this historic dichotomy, perhaps within the African American community—maybe reflected most of all in the conversations between Du Bois and Booker T. about economics versus politics, or economics versus culture and political power? Of course, the man to the left of King, or forever noted in popular culture, was Malcolm X. Could we position then Jackson as the Booker T. in these debates in the civil rights era of the '60s? Or is that the wrong way of thinking about it?

05:44 - David Masciotra: Well, Jackson—and I would argue, I mean, I'll just say it, as one could gather from the title of my book, I give a very favorable assessment of Jackson’s life and legacy.

06:01 - Andrew Keen: Yeah, I mean, that goes without saying. I don't think we’re, certainly two days after his death, we’re not in the business of criticizing him.

06:08 - David Masciotra: Yes, and he also, I should say, became a good friend. I spent a lot of time with him, and I was privileged to call him a friend. But he often found a way—and I would say it wasn’t as a calculating operator—he found a way to occupy space between two positions. So, for example, after King's death, he often acted as a mediator between the old guard of the civil rights movement coming out of the South and the Black Panthers in major cities such as Chicago, where Jackson was located.

06:48 - Andrew Keen: And Oakland, of course, up the road from me.

06:51 - David Masciotra: And to your question, the Booker T.–Du Bois dichotomy, Jackson was a consistent preacher of uplift—economic uplift and educational uplift. In fact, his organization, Operation PUSH, had an arm called PUSH-Excel that went into Black schools and tried to teach and inspire educational ambition and excellence. But as Jackson began to learn, the systemic obstacles and impediments to such a program were so large that he eventually entered into political life quite directly, running for President of the United States in 1984 and 1988. And in doing so, registering millions of voters—Blacks, Latinos, Native Americans, Asians—he was the first candidate to fully support gay rights running for President. And the mission of that task was to try to transform the Democratic Party into a political apparatus that could fully represent multi-racial, multi-cultural America and become an advocate for more progressive economic policies.

08:14 - Andrew Keen: David, the Economist ran an obituary yesterday which I thought had a rather patronizing title—I'm not sure how patronizing the obituary was—it said, "Jesse Jackson Made a Black President Possible." Is that true? What does that actually mean? Is that one of his great legacies, that you had to have a guy like Jesse run first to get to Obama?

08:39 - David Masciotra: Well, it's true, and it's also—but it's also patronizing. I agree with you. It's true in two senses: the cultural sense and the political sense. So, Obama himself has said that when he was a student watching Jackson debate all of his opponents in the primary, he himself thought, you know, "One day we will have a Black President" because Jackson, even though he didn't win those races, because of his brilliant oratorical ability was besting all of these senators and governors in the debate. Then there's a little bit of inside baseball, so I'll abridge it, but in 1984, Jackson won 20% of the vote but received only 8% of the delegates. In '88, he won approximately 40% of the vote and nearly as many delegates. And that was because he and his team made a big push lobbying for proportional allocation of delegates. So, if a candidate gets 35% of the vote in a state, they get roughly 35% of the delegates. That was critical because Obama, in 2008, won mostly small states, whereas his opponent, Hillary Clinton, won most of the large states. So, without proportional allocation, Obama would have never won that nomination and become President. But you're correct that it's patronizing, I would say, because Jackson—his greatest political accomplishment was building, to use his terminology which he borrowed from the Black Panthers, a Rainbow Coalition. And he was also an international figure. He did work, for example, in Syria, Iraq, Cuba, Gambia, and Algeria to free political prisoners and hostages. So, to try to relegate him to merely someone who made a Black President possible—even though he was undoubtedly a great Black civil rights leader and freedom fighter—is patronizing, and it is reductive because he had an international vision and he attempted to include all Americans in his domestic iteration of political activism and leadership.

11:15 - Andrew Keen: I wonder if in the future, AOC perhaps becomes President; when Bernie Sanders dies, he might get a similar kind of obituary from the Economist that said "Bernie Sanders Made a Radical Left President Possible." That's perhaps a conversation for another show, David.

11:34 - David Masciotra: Well, but you make a good point because that's I think part of the problem with mainstream American political discourse is that it has a very narrow, even myopic fixation on elections and electoral numbers. It's almost like sports coverage and, you know, "Who won? Who made the win possible?" Whereas we have to leave some room for not only political philosophy and larger cultural ideas and trends, but also an understanding of history that—to return to one of Jackson's favorite metaphors, and he wasn't alone in using it—it's not about the sprint, but it's the marathon. And as that headline shows, even if it's reductive, but many other things can show, even when Jackson lost the sprint, because he was a visionary, he'd often win the marathon.

12:35 - Andrew Keen: Well, he was an all-rounder. I think that's—sometimes all-rounders don't have one particular specialization. He wasn't either a sprinter or a marathon runner, he could do both. David, you’re a white guy called Masciotra with a very Italian last name from the suburbs of Chicago. You wrote this book, it’s one of the two or three most respected biographies, although it’s not particularly a conventional biography, of Jackson. I know you spent more than 100 hours with the guy; as you said, you considered him a friend. Firstly, how did you get into Jackson? How did you get so much access to him? He must have been a pretty nice guy to give you so much time.

13:25 - David Masciotra: Yeah, well, to take it from the beginning, even growing up white in the Chicago suburbs, I lived in a household where people admired Jesse Jackson. My mother is a very dark-skinned white woman because she's Serbian; my father’s the Italian one. And as a young girl growing up in a Chicago suburb of Thornton, there weren't any Black residents in town, there weren't any Latinos, so she became the target of racist animus and schoolyard kids would hurl racial slurs at her. And when she heard Jackson's rallying cry of affirmation, "I am somebody," it inspired her and it instilled self-confidence and self-belief. My grandfather, who worked in a material service quarry, he always saw Jesse Jackson as a great hero because of the extensive work that Jackson did with labor unions and on behalf of blue-collar workers. So, I grew up in this household with admiration for Jackson, and he very early became a political hero of mine. And there's an old expression, "Never meet your heroes," but when I met Jackson in 2014 to interview him for the first time on the occasion of the 30th anniversary of his first presidential campaign, we had a great rapport, and I found him very kind, very generous. And I continued to arrange interviews with him, and I spent six years covering him before writing this book that we’re discussing, I Am Somebody. And it was a real professional honor and gift. It was quite an extraordinary political education. You know, I earned a Bachelor's degree in Political Science and, with no disrespect to my great professors, I have to say I learned more about politics in one week with Jackson than I did in four years at university. And I was blessed to develop a friendship with him. And I'll say that the common rap on Jackson that is critical—and the New York Times obituary even repeated this—is that he was a camera chaser and publicity hound, and his ego always interfered with his leadership. I found a person who was committed, sincere, and often doing things that were quite inspiring and quite moving, far removed from television cameras. So, maybe that expression "never meet your heroes" is generally true, but my respect for him grew after getting to know him personally rather than diminished.

16:32 - Andrew Keen: Seems a very open-minded guy. Last year, you and I did a show when Kamala Harris chose not to go on the Joe Rogan show, and you spoke about Jackson’s decision to debate David Duke back, I think it was in 1988, when Duke declared for President. What can we learn about that chapter in Jackson's life in terms of making sense of his significance, especially given the fractured nature of American politics these days and someone like Kamala Harris? I mean, her refusal to go on the Rogan show, perhaps because she didn't want to offend her young staff, is really very troubling. You and I talked about that last year.

17:15 - David Masciotra: Yeah, I mean, no one could accuse Jackson of being wishy-washy. He had his principles, he always spoke eloquently but plainly about where he stood, and he could often speak with contempt for people he felt were agents of racism and injustice and other forms of bigotry. But he was also a true believer in free expression and open discourse. So, he would debate just about anyone, including a former leader of the Ku Klux Klan such as David Duke, because he believed that the way toward progress is enlightenment, and one cannot become enlightened if one is shirking from debate, closing conversation, censoring people with views that we may even find abhorrent. But instead, the promise of democracy is one of confrontation and intellectual combat. You know, he was a big believer in non-violence, having learned that from Dr. King, who learned it from Gandhi; but non-violence does not mean passive or withdrawn. It doesn’t even mean non-confrontational. So, his willingness to confront someone like David Duke and attempt to diminish and discredit him through the power of debate and the power of political persuasion should serve as yet another lesson for young Democrats and young progressives who think that they're somehow brandishing moral virtue or claiming the moral high ground when they refuse debate. Jackson would have understood that the refusal to debate only empowers one’s enemies. Instead, the way to diminish one’s enemies or opponents is to engage the debate and show why your ideas are superior and why your method of leadership is more beneficial to a broad spectrum of society.

19:25 - Andrew Keen: Yeah, and it’s worth noting that he wiped the floor with Duke. In fact, someone should—I don't know if they already have done—someone should make a documentary or a movie about this experience because by speaking to Duke didn't mean in any way, as you note, that he was in any way agreeing or even respecting Duke’s position. And intellectually, he wiped the floor with him, didn't he, David?

19:50 - David Masciotra: Yes, yes. In fact, even Duke himself, who looked quite embarrassed and was reduced to sputtering at the end of the debate, said, "Well, Jesse Jackson’s intelligence isn't typical of Blacks."

20:10 - Andrew Keen: Oh my God. He really said that?

20:12 - David Masciotra: Yes, yes. So, I mean, that was his way of once again amplifying his hideous, grotesque racism, but also conceding that he had lost the debate. And imagine had Jackson said, "No, I won't deign to have a conversation with Duke." I mean, Duke could have claimed, "Well, Jesse Jackson is too cowardly to face me." But instead, Jackson reduced him to a sputtering mess.

20:43 - Andrew Keen: The title of your book, David, is I Am Somebody. I know that Jackson appeared on Sesame Street in association with this phrase. Why did you choose to name the book I Am Somebody? And what did Jackson say? Is this a kind of a cultural pride in some ways?

21:03 - David Masciotra: So, the origin of "I Am Somebody" is after King's death, there was a Poor People's March on Washington. And Dr. King was trying to organize this in the last weeks of his life. He hoped that poor people of all different races and religions could convene on the National Mall and recreate the 1963 March on Washington, but do so to combat systemic poverty as opposed to systemic racism. Well, King's assassination took the wind out of the sails of that effort. They proceeded with it, but it was very low attendance, and it looked like a failure in the eyes of the national press. So, Jesse Jackson giving a closing speech thought to himself, "What can I give to these people, knowing that we're leaving politically empty-handed and with a media defeat?" So, this old poem came to him and he refashioned it for his own purposes as an affirmative cry. He would say, "Repeat after me: I may be poor, but I am somebody. I may be Black, but I am somebody. I may be in a wheelchair, but I am somebody." And this was something that he did throughout his entire life; it became his signature line in countless speeches. I used it as a title because it not only captured the dramatic trajectory of his life—growing up poor to a single mother in the Jim Crow South and becoming one of the most recognizable and influential international civil rights leaders—but also because I thought it captured the full essence of his radical form of democratic engagement and politics: that is to express, affirm, and celebrate the essential somebodiness of every human being, whether they were the gay men dying of AIDS by whose side he slept in hospices in the 1980s, or the Latino immigrants with whom he marched from California over the border into Mexico in the 1980s, or all the inner-city Black people who he did his best to represent as a civil rights leader, as a politician, as a cultural force. "Somebodiness" was at the heart of how he envisioned democracy and how he envisioned political potential.

24:06 - Andrew Keen: "Somebodiness." CNN called him quote-unquote "a racial," and they’re quoting, "pathfinder." I’m not sure entirely what that means. New York Times, in response to Jackson's death, notes that it arrives at a crucial moment for Black political power. I think there has not been a crucial moment for Black political power probably in the history of the Republic. You wrote an interesting piece for UnHerd suggesting that Jackson transcended America's racial politics. In your mind, what can Jackson tell us at this moment in February 2026? Trump used his death to attack Democrats, surprise surprise. How can he help Democrats fight back politically against Trump and MAGA?

24:59 - David Masciotra: Well, Jackson was able to do something quite interesting, and I believe that the Democrats ignore it at their own peril by splitting off into two camps. There's a camp of the Democratic Party that believes the party should lead with identity issues, for lack of a better term, and then there is a camp of the party that believes that the Democrats should lead with class issues. When Jackson ran for President, he sought to demonstrate how those two missions within electoral politics are inextricably linked and that under a rubric of fighting for a more just and inclusive and fair society, one cannot substitute race for class or use race to erase class. So, for example, a great moment during the—well, you mentioned my UnHerd article, I’ll tell that story.

26:07 - Andrew Keen: And this came out yesterday or a couple of days ago, so it’s very recent. I will link to it in the shownotes. It’s in UnHerd, "Jesse Jackson Transcended America’s Racial Politics."

26:20 - David Masciotra: Yes, and I have a much longer tribute that will run this weekend in various other places. But I was with Jackson in 2015 in his home state of South Carolina; he was there to try to convince then-Governor Nikki Haley to do two things: accept Medicaid expansion funds from the Obama administration and also remove the Confederate flag from government property. He was, as part of that tour, speaking in a Black mega-church, and he emphasized a few times that the expansion of Medicaid would actually benefit more whites in the state of South Carolina than Blacks. During the Q&A session, a young woman who seemed quite angry with Jackson said, "Why are you bothering to talk about white people? Aren't we enough?"

27:18 - Andrew Keen: And this was a young Black woman, I’m presuming.

27:21 - David Masciotra: Yes, and she said, "Why are you bothering to talk about white people? Aren't we enough?" And I think I was the only white person in the church, so I felt a few eyes turn toward me as if there was anything I was supposed to do or say about it.

27:36 - Andrew Keen: You should have said, "Well, I'm a Black Serbian."

27:40 - David Masciotra: Right. And Jackson told a story about when he visited the Soviet Union; all of these young Russians came up to him and they wanted to talk to him more about music than about politics or the Cold War. Even though he wasn't a musician, they asked him questions about Ray Charles and Aretha Franklin and Motown. And he said, "Now imagine if Diana Ross and Smokey Robinson and all the great musicians of Detroit had just stayed in their neighborhood and made music for themselves." He said, "If we can start something beautiful on our side of town, and if we take it to the other side of town, we make the whole town better." And he would often say that you have to see the world not through a keyhole but through the entire doorway. So, when I say that Jackson, even though he made racism and racial issues a main focal point of his political life, when I say that he transcended racial politics, it's because he had a universal vision. The Rainbow Coalition thing wasn't just a slogan; he sought to bring all of these different groups together. Sometimes he failed, sometimes he succeeded, but it was a noble mission, and he put it very well during his presidential campaigns when he said, "If we leave the racial battleground to find economic common ground, we can reach for moral higher ground." And one white family farmer in Iowa reacted to that by saying, "Who would we farmers rather have in the White House? A Black friend or a white enemy?" So, if there’s to be any chance for the success of democracy in the United States, a country as diverse as ours, it’s predicated upon that universal vision, and that's the vision that Jackson expressed, that Martin Luther King expressed, and then a man who we both admire, Robert Kennedy, expressed. That's the vision that could serve to enhance and strengthen American democracy at this moment that it appears to be under terrible threat.

30:26 - Andrew Keen: Are you suggesting then that his Rainbow Coalition was prescient in the sense that it represented a progressive kind of populism to be able to counter the racialized right-wing populism of Trump and MAGA? That in a way, I know Jackson wasn't very well towards the end of his life, but he probably wouldn't have been dramatically surprised by either the success of Trump or of MAGA.

30:57 - David Masciotra: Yes, you know, I spent a lot of time with him in 2016, and Jackson, more than most Democratic leaders—more than most establishment-type liberals—was very concerned about Trump’s chances of winning. And he saw the MAGA movement as not only backlash against the progress of the various rights-based movements of the '60s and '70s, but one of populist fervor, a certain type of populism. And Jackson consistently represented the opposite side of populism: the populism that attempted to humanize powerful institutions in the interest of ordinary people, whether that was the large banks that he opposed and lobbied to introduce more racially equitable policies, or whether that was the two major political parties. Obviously, he was a lifelong opponent of the Republican Party, but a major part of his 1984 and 1988 campaigns and the work he did subsequently, even as he had one foot in the door of the party maintaining friendly relations with people like the Clintons and others, was to push the party in a different direction, one that was more responsive to the needs and the demands of ordinary people. In fact, he said that in '84 and '88, when he gave those masterful speeches at the conventions, he had more supporters outside the arenas who were protesting on behalf of Native American rights, gay rights, immigrant rights; he had more people outside those arenas supporting him than he had on the inside. And what he was trying to do was act as an usher to bring those people inside the party so that the party would have real populist energy and passion fueling it.

33:23 - Andrew Keen: Finally, David, as I said, you’re the author of one of the most distinguished books on Jackson, I Am Somebody. It’s not a conventional biography, but you’re not a conventional biographer; you’re a cultural historian, you’re a polemicist, you do all sorts of different kinds of journalism. What's the experience of writing this book, I Am Somebody, about a great American, Jesse Jackson? What’s it taught you about how we should remember great Americans, both as intellectuals like yourself—guys who write books about these people—but also as fellow Americans, whether it’s Jackson or MLK or JFK or Bobby Kennedy or even Trump? What does it teach us about how great Americans operate and how Americans should think about them, remember them, and indeed critique them? Because I know, as you know, Jesse Jackson was far from perfect.

34:25 - David Masciotra: Yes, of course. I mean, he was, as Tavis Smiley has often said about Jackson, he wasn't a perfect servant, but he was a public servant. You know, Jackson was a visionary, and I think that writing about him demonstrates the importance of leadership. There are many on the left who start socio-political movements, such as Occupy Wall Street or Black Lives Matter or Me Too, and they want to have a leaderless effort because they believe that that better expresses aspirations toward equality. But any successful social movement, whether it's for the good or the ill of society, has strong leadership because leaders have the power to inspire and, without inspiration and without direction—leaders also have the power to give direction—without inspiration and without direction, we’re often lost. So, there's that aspect of it, but then there's also in his eulogy for Rosa Parks, who’s another great American, Jesse Jackson said that one of the reasons Rosa Parks was so successful was simply because she was available. And any of us can make ourselves available in service to a good cause, and that's also part of why he wanted people to repeat the words "I am somebody." We shouldn't delude ourselves into thinking we can all become Jesse Jackson, but we can all have a positive impact. And that too is part of the promise of democracy.

36:26 - Andrew Keen: Do you think in 50 or 100 years, final question David, people will be writing door-stopping books on Jackson—the kind of books now that get written on, I don't know, George Washington or Abraham Lincoln or FDR or JFK? Or do you think in 50 or 100 years he’ll be forgotten, he’ll be just another nobody? Or will he remain a somebody?

36:50 - David Masciotra: I think people will continue to study his work; his accomplishments are myriad, and I think that in the coming years, his influence will only grow more obvious. And I should say that when I started writing about Jackson in 2014, I was almost all alone because at that point, we were in the Obama years and we had this post-racial hallucination, and most people viewed Jackson—and by most people, I shouldn't say most people, but most the most influential people in the press who were dictating the terms of our national conversation—they viewed Jackson as passé. And twelve years later, you could see from the outpouring after his death, he’s anything but passé, but people are beginning to appreciate that he was a visionary and that he has much to teach us.

37:54 - Andrew Keen: Wow, he has much to teach us. I think, David, because among others you've written a wonderful book on him, I Am Somebody: Why Jesse Jackson Matters. He matters as much now in death as he did in life. We'll connect with the book in our shownotes too. As always, David, real pleasure and honor to have you, and I think America is lucky to have a guy like you able to think counter-intuitively and write this wonderful book about Jackson whilst everybody else wrote him off. Now they’re not, and you're the one who is ahead. Thank you so much.

38:35 - David Masciotra: Thank you very much.

38:43 - Andrew Keen: Hi, this is Andrew again. Thank you so much for listening or watching the show. If you enjoyed it, please subscribe. We’re on Substack, YouTube, Apple, Spotify, all the platforms. And I’d be very curious as to your comments as well on what you think of the show, how it can be improved, and the kinds of guests that you would enjoy hearing or listening to in the future. Thank you again.