Over the past few months, I have plowed through two biographies of prominent Black men. I read them back-to-back not out of any specific design; they were both men who loomed as distant but intriguing figures in a certain era of my life, and they both happened to put out biographies at the same time. Reading both proved more taxing than my usual, perhaps because I am still trying to understand what led me to make the decisions I made toward the end of my time in the city that defined both of them, still imagining lives not lived, and forever intrigued by the shadows cast by giants.

I started with Barack Obama’s autobiography, A Promised Land. The former president’s tome is a doorstop that takes a feat of endurance to complete. At times the detail is excessive, but to err on this side is, I suppose, preferable to omission, and long-windedness lends itself to an added level of candor. For the political biography genre, it is uncommonly introspective. Obama explains how torn he was at certain moments, shows some of the strain of political celebrity on a man who wanted the freedom to roam the streets and to be an attentive husband and father. In the end, he finds ways to rationalize his courses of action, an apologia for a presidency that was far from perfect but managed to maintain its guiding lights.

Obama’s first term coincided with my full political awakening, his journey to Washington tracking on to my own in the fall of 2008, and I relived those years viscerally as I read his book. The formative events of his first term were the formative moments of my political education, my venture into my own Promised Land at Georgetown. Being in DC gave me a window to the party outside the White House on election night, and to that cold inaugural morning on the Mall. Sitting in the University of Minnesota Duluth library while home for the summer, ostensibly doing research for one of my Georgetown professors, I read up on the Deepwater Horizon oil spill and started churning out a jumbled essay on meritocracy, which was my first step into this halfhearted world of punditry that I still inhabit. In the spring semester of 2011, fresh off a semester abroad and hungry for some proof that the arc of history still tilted toward freedom and liberal democracy, I glued myself to the nascent revolutions sparking across the Middle East. A feed of Al-Jazeera English, live from Tahrir Square, ran constantly in the background in my cozy hole of an off-campus bedroom, through hope-filled days and tumultuous nights and the fall of Hosni Mubarak, the Arab Spring briefly living up to its name. A few months later, a loud exclamation from the living room of that same house led me downstairs to find my roommates gawking at the announcement that Navy Seals had killed Osama bin Laden. I was in the seat of history, bound up with the trials and tribulations of the world my president wanted to make.

Despite the achievements of his first term, the world did not become the one Obama envisioned in his lofty words. This complication still gnaws at me, perhaps because some of Obama’s more prominent character traits map on to a few of my own. Always ready to listen, loyal to a fault, a man capable of grand words but whose default course through life tends to settle more on the side of what George Packer calls “ironic realism,” a dogged focus on the levers that are actually within one’s grasp. This instinct to campaign in poetry and govern in prose is a major part of why the 2008 election, which so many observers expected to be a landmark shift, turned out to be a very momentary high-water mark for the Democratic Party. Obama was not the transformative figure some of his supporters mistook him for, but simply being who he was proved enough to ignite a vicious opposition.

One of the most poignant moments come in Obama’s observations of Manmohan Singh, the Prime Minister of India through much of his term. Singh is, in some ways, the hero of the triumphant quarter century of liberal democracy that ran from 1990 to 2015 or so. As India’s finance minister in the 1990s, he perhaps did more to lift people out of poverty than any human alive, and once he took control of the Lok Sabha, his administration was one of firm commitment to democracy and technocratic competence. He was, in a way, an elder statesman version of Obama: a member of a minority group with a fraught history vis-à-vis the national majority noted for his thoughtfulness and decency. But Singh’s faults were the faults of the era: he was the anointed caretaker of a political dynasty that was running out of gas, tinkering at the margins and creating a space for people to live their lives, but aspiring to no great change, “just the observance of rules that allowed us to sort out or at least tolerate our differences, and government policies that raised living standards and improved education enough to temper humanity’s baser impulses.” In this more aged version of himself overseeing a ricketier system, Obama begins to see, and is chilled by, just how easily it could go wrong. “Now I found myself asking whether those impulses—of violence, greed, nationalism, racism, and religious intolerance, the all-too-human desire to beat back our own uncertainty and mortality and sense of insignificance by subordinating others—were too strong for any democracy to permanently contain.”

Some critics portray Obama’s cool realism as a failure, and certainly there are some aspects of that mentality that can lead to blindness over some of the forces that were at work at in American society at the same time. But an acceptance of limits is still one of the most mature traits a politician can have, and is why so many of the ones with a talent for soaring rhetoric and righteous Tweets prove rather ineffective at actually achieving any of the things they set out to achieve. The question, of course, becomes one of where that line is between ironic realism and a resignation that cuts off the possibility of any sort of achievement, and just how content one can be with incremental progress or a gradual turning of the ship.

The limitations of the Obama way of being has led me to explore alternatives, and a second book took me back to the same time period, but for very different reasons. John Thompson, Jr., the iconic Georgetown basketball coach who I eulogized on this blog after his passing last year, has published a posthumous autobiography, I Came as a Shadow. While co-written with Jesse Washington, it is most certainly in Big John’s voice: blunt, certain, unapologetic. The book traces his journey from Southeast DC projects to the Celtics to his long tenure at Georgetown, where I, as a sports-loving freshman, ate up the story of his reign over the Big East. But the book is less a basketball book than a treatise on race in America and one man’s journey to smash any and all obstacles that dynamic imposed upon him. “Who wants to be equal to the next guy?” he asks. “I want to kick his ass.”

Thompson proceeded to kick many asses during his tenure with the Hoyas, both as he whipped his own players into line and as the on-court results cemented his reputation as one of college basketball’s great head coaches. He did it amid a torrent of abuses, obvious and hidden. He wore glasses to look learned and forced his players into suits, the results of a lifelong process of studying the white man and learning to win on his terms; he reveals that his all-Black teams were not for a lack of effort to recruit white players. At times he seems like just a good partisan coach, as when he questions refs’ motivations. But while reading the book, I re-watched the 1984 national championship game, and was struck by how composed he was. He doesn’t come across as a screamer or a radical, and yet here he is, getting labeled “the Idi Amin of college basketball” because he was big and Black and had his big, Black players run a full-court press. (Thompson’s response to this charge is classic: “Amin was a Ugandan dictator who killed thousands of innocent people. I’m still trying to figure out who I’m supposed to have killed. Maybe Oregon State, because we beat them 69-45 to reach the Final Four.”) Above all else, he unsettled some observers because of the totality of his control.

Georgetown and Thompson were a fascinating odd couple: a Catholic school from a place famed for its establishment cocktail parties that went and hired a Black man who ran the nation’s most transgressive basketball program. Race, Thompson argues, is exactly the reason he was hired: he’d achieved some success as a coach in the DC area just as Georgetown was starting to think it had to do more for Black people in Washington in the aftermath of the riots following Martin Luther King’s assassination, and Thompson allowed the school to check a lot of those boxes. Basketball played no small part in giving Georgetown its national reputation, and Georgetown gave Thompson a platform to prove himself right about everything he believed in. Thompson largely praises the Georgetown administrators who let him be himself, even as he casts his stare on the institutional constraints that both created Georgetown and keep it as it is. The book concludes with the revelation from several years ago that Georgetown sold a bunch of slaves in 1838 to preserve its existence, and with Thompson’s speculation that his own ancestors were almost certainly among those very slaves.

Thompson makes passing mention of his respect for the Obamas, and like the basketball-loving former president, the coach can see the complexities in American race relations and is much more nuanced than the 80s press sometimes made him out to be in popular imagination. But when it comes to ways of being in the world, it’s hard to imagine a much bigger gulf. Obama carefully calibrated everything he did, weighing options and testing waters, ever seeking that ideal of democratic consensus, wrestling with processes and seeking input and collaboration. Thompson, on the other hand, simply did things his way. Part of that divide probably just stems from the nature of their realms; at the end of the day, for all his justified insistence that he was more than a basketball coach, Thompson’s record still falls heavily on wins and losses, while judgments of Obama run through the much murkier and subjective world of politics. But Obama and Thompson come off as diametric opposites in temperament and approach.

Or were they? Both men are scholars at their core, with Obama’s Harvard Law instincts and Thompson’s undying insistence that his players come for the education. Both were trailblazers, but knew they had to do what they were doing on society’s terms: Thompson always speaks of studying the white man and learning his ways, while Obama’s broad appeal has its roots in an expansive view of the American Dream that has its most obvious roots in the very white realm of midcentury American liberalism. Both men were integrators, not assimilationists or among those who sought revolution. They wanted a world in which what they stood for was not radical at all.

That, however, was not the world in which Thompson or Obama lived. Their circumstances did not allow for such anonymous walks down the street. We could debate their methods and the extent of their successes ad nauseam; in fact, we should, and they would both probably appreciate recognition on those terms. But the reason I’m reading their biographies now is because of what they did in the face of a world that would not allow them that anonymity. It is because they had the insight to know their worlds were not quite right yet, and because they had the tenacity to use the tools before them to change those worlds. They were men in the arena.