Heroism is essential to politics. We live for the hour when a politician stands up in Theodore Roosevelt’s dusty arena and we recognize, with astonishment, that here is a person prepared to take risks, tell us what we don’t want to hear, face possible defeat for a principle, tackle insuperable odds, and by doing so, show us that politics need be not just the art of the possible, but the art of the impossible.

We are short of heroes everywhere these days, but particularly in politics. The Arab Spring appears to have consumed the leaders who rose up in the Cairo streets. In Burma, Aung San Suu Kyi has learned that it may actually be easier to be a saint than a politician. For the moment at least, she seems to have lost the moral voice she once possessed in captivity. There are political heroes aplenty in China, but most of them are in jail. In Russia, heroic resistance to tyranny survives in the offices of Memorial, the nongovernmental organization now suffering persecution; elsewhere, the political elites are cravenly riding in Putin’s chariot, even if they have no idea where he is taking them. In Europe, Angela Merkel inspires respect for competence, not for courage; François Hollande struggles to convey authority; and David Cameron seems content to be an imitation of a prime minister, not the unyielding, decisive thing itself. As for President Obama, he had courage in abundance once, when he launched that seemingly impossible bid for the presidency. Now, as we commend his prudence and circumspection, we also ask, where has his audacity gone?

To find courage in the public realm, to remember what it can do to transform our hopes for politics itself, we have to go back to the canonical leaders of 1989 and 1990. The times demanded bravery, and leaders aplenty rose to the occasion. Gorbachev showed courage in not using force to hold his empire together. Mandela’s toughness and magnanimity guided South Africa from apartheid to black majority rule. In Poland, the shipyard worker Lech Wałęsa led his country to freedom. In Czechoslovakia, a playwright named Václav Havel defied imprisonment and intimidation to become the president of a free country.

A magnificent biography of Havel, by Michael Zantovsky, allows us to take the measure of his heroism in a new and complicated way. It helps us to think about the mystery of courage—why, in the case of Havel, bravery managed to take command of such a mild, inward intellectual, and such a flawed human being. The surprises in Zantovsky’s depiction begin with the photograph on the cover. Havel is disheveled, in a rumpled sweater over an open-necked shirt, running a hand through unkempt hair. He looks as if he wants the photographer to leave him in peace. Here is a man at bay, tired, disconsolate, at a loss for words—a man thinking, What the hell has happened to me?

Seeing a hero in disarray delivers a jolt. We’d much prefer to remember the triumphant images of a vanished era, when Havel spoke to a thronged Wenceslas Square in November 1989, when the “power of the powerless” propelled him from prison to the presidency. For those in my generation, who came of age in 1968, he defined what it was “to live in truth,” as he put it—what it was to wield political power without, or so we believed, being destroyed by it.

We tend to think of heroism as mysteriously individual, but Havel’s life teaches us that it is in fact a social virtue.

Zantovsky, who was Havel’s press secretary and good friend, asks us to leave behind the heroic image and follow him offstage. He pulls back the curtain to reveal the Havel whom his closest associates knew and sometimes had to endure. Gradually a portrait comes into focus of a chain-smoking, often hungover, sometimes debauched, frequently strung-out mortal who struggled with the demands of power and with an unruly personal life. We learn that he constantly betrayed his wife, Olga, the brave woman he considered his moral lodestar. He tried to square this circle by confessing everything, if not before then after his serial desertions. Olga endured his infidelities in silence, occasionally taking a lover of her own and ultimately forging an independent public persona as Czechoslovakia’s first lady. Not long after she died in 1996, Havel shocked many of his admirers by marrying the young actress who had been his mistress all through Olga’s final illness.

Heroes inevitably disappoint. What makes Havel so interesting is that he disappointed himself. No one was a more ruthless judge of his own failures, both personal and political. The country he wanted to hold together fell apart during his presidential tenure, into the Czech and Slovak Republics, and its political culture strayed far from his moral convictions about public life. A reckoning with Havel’s trajectory is also a reckoning with an entire generation of Eastern European dissidents, the revolution they led, and the revenge that history has taken on their dreams.

Havel was born into privilege in 1936, the son of a Prague developer who built exclusive modern villas on the Barrandov Hills. It is crucial to any account of Havel’s courage that we remember he was born into a Czechoslovakia shaped by the presidency of Tomáš Garrigue Masaryk. Without Masaryk, another liberal intellectual who guided his country to democracy, there might have been no Havel. Without the assurance instilled by a privileged upbringing, too, Havel might have doubted his right to be courageous.

Within two years of Havel’s birth, Masaryk’s Czechoslovakia was betrayed at Munich. Then came the German occupation, the war, and afterward 41 years of Communist dictatorship. The Havel family survived the Germans and held on to some of its property after the Communist takeover in 1948, but Havel’s bourgeois origins barred him from formal education and hence a career in postwar Czech society. Exclusion was painful, but it had its advantages. It may have helped keep him honest.

In 1990, when Havel received an honorary doctorate at the Hebrew University in Jerusalem, he wondered aloud, in his acceptance speech, about what being excluded as a “class enemy” had done to his psyche:

The hidden motor driving all my dogged efforts is precisely this innermost feeling of mine of being excluded, of belonging nowhere, a state of disinheritance, as it were, of fundamental non-belonging.

The operative word here is disinheritance. Born into the ruling elite of Masaryk’s Czechoslovakia, Havel always treated his Communist persecutors as callow usurpers. His privileged birth also helps explain his famous politeness, and something less obvious as well: his learned helplessness, which his biographer shrewdly realizes was the trait that Havel used, knowingly or not, to bind others to him:

Whether this was his small, somewhat frail physique, his soft demeanour, his explicit acknowledgements of helplessness, ignorance, confusion, fatigue and despair, he seemed to be constantly in need of help, to radiate a permanent Mayday signal, causing a large number of people to rush to his rescue, to offer sympathy, help or tender care … Sometimes it seemed as though he were himself the ultimate embodiment of the power of the powerless, a man who could achieve almost anything by making clear his utter inability to do it alone.

We tend to think of heroism as mysteriously individual, but Havel’s life teaches us that it is in fact a social virtue, nurtured by loyalties to people you know you must defend if you are to live with yourself afterward. Havel, the defrocked bourgeois, found his first real home in Prague’s dissident theaters of the early 1960s. He fell in love with the backstage world of props, stagehands, lighting guys, makeup girls, and sweaty dressing rooms, and with the after-show parties at the bars, restaurants, clubs, and cafés of the old town. This was the world where he forged the loyalties that made heroism possible, and where he wrote the plays, such as The Garden Party, that made him a national and then a European celebrity.

The audiences who flocked to see his work in Germany and Austria embraced Havel as the latest exponent of high European modernism. But for the young Prague audiences of the 1960s, the plays struck home as astute parodies of the surreal propaganda bubble in which the Communist Party sought to enclose them. Havel had a brilliant comic gift for satirizing the party’s fatuous clichés, and this artistic lucidity, this insight into the hollowness of the apparatus of fear, helped make him fearless. In realizing that the totalitarian regime could make people afraid of it, but could never make them believe in it, he found the hope that courage feeds on. As he later noted:

Isn’t it the moment of most profound doubt that gives birth to new certainties? Perhaps hopelessness is the very soil that nourishes human hope; perhaps one could never find sense in life without first experiencing its absurdity.

By the mid-1960s, all along Národní Street in old Prague, a brilliant generation of artists, dramatists, novelists, filmmakers—Jiří Menzel, Milan Kundera, Miloš Forman, the philosopher Jan Patočka—had created an audience of young Czechs who were, in effect, living in truth, outside the propaganda bubble, in a prefiguration of what the dissident Václav Benda was to call a “parallel polis.” The authorities, with the condescension of the powerful, permitted this polis to emerge, because they never imagined that those in it might one day overthrow them.

This miscalculation proved fatal. By 1968, the parallel polis had become so powerful that it pushed the Communist authorities, led by Alexander Dubček, toward the limited opening known as the Prague Spring. Havel took little part, aside from one night when he drank too much and lectured the astonished Dubček about the reform process. He refused to lend Dubček a hand, because he had nothing but scorn for those who thought communism could reform itself into “socialism with a human face.” In this, he showed shrewder judgment than the novelist Milan Kundera. After the Prague Spring was crushed by Soviet tanks in August 1968, Kundera wrote an essay called “The Czech Destiny,” urging Czechs to persevere with the project of reforming communism. Havel was scathing in reply: better, he said, to “face a cruel, but open-ended present” than to indulge in senseless dreams. He and Kundera, who went into exile in France just a few years later, never repaired the breach.

In January 1969, Jan Palach, a philosophy undergraduate, burned himself to death in Wenceslas Square to protest the Soviet invasion. Unlike most of his fellow dissidents, Havel did not react to Palach’s death with tears, desperation, or hopeless rage. Instead, like the politician he was to become, he gave a television interview in which he declared, with strange—and up to this point uncharacteristic—bravado, “There is just one road open to us: to wage our political battle until the end … I understand the death of Jan Palach as a warning against the moral suicide of all of us.” Moral suicide—taking a job with the regime, informing on your erstwhile dissident friends—became a standard if depressing mode of collaboration in the 1970s. The parallel polis collapsed, leaving the few remaining dissidents to face the full pressure of the regime alone. Of that long decade, Zantovsky writes, “few … can imagine the twilight mood, the torpor, which resembled a state of semi-anaesthesia.”

Remarkably, this was the very period in which Havel slowly transformed himself into the leading figure of the Czech resistance. The evolution was neither immediate nor inevitable. Indeed, it took some strange twists and turns. In what looks like an attempt to refute the regime’s charges that he was a bourgeois parasite, Havel even took a job for nine months rolling barrels in a brewery, commuting in a black Mercedes. The work was cold, numbing, and mindless, but writing saved him, enabling him to turn deadening experience into resistance and revolt. Out of his stint in the brewery, he wrote a play called Audience, which, after its premiere in Vienna in 1976 (the Czech regime forbade Havel from attending), was hailed as a satire on the “worker’s paradise.”

In 1975, Havel wrote a defiant open letter to Gustáv Husák, the general secretary of the Communist Party, pointing out that the “normalization” of society after the Prague Spring had only resulted in the “calm of the morgue or the grave.” He went on, “In trying to paralyze life, then, the authorities paralyze themselves and, in the long run, make themselves incapable of paralyzing life.” After this declaration of war, the regime made a concerted attempt to isolate him from the city’s theaters and from his friends. It was a preview of intimidation to come, when the police camped outside his Prague apartment and his country home, and he and his friends were repeatedly brought in for questioning.

During this period, when no one could possibly imagine that a challenge to the regime would ever succeed, Havel discovered—in the words for which he is best remembered—that hope “is not the conviction that something will turn out well, but the certainty that something makes sense, regardless of how it turns out.” Those are words you have to earn the right to say, and Havel did that, not just through endurance but also through failure and shame. Under pressure, he did not always stand up. Once, he broke—and the painful lesson he learned from his own weakness helped make him both a more humble and a more resilient leader.

In January 1977, he and a tiny group of dissidents founded the human-rights organization Charter 77; the Soviets, in the Helsinki Final Act, had agreed to allow such groups in return for Western recognition of their hegemony in Eastern Europe. Charter 77 eventually grew into the movement that brought the regime to its knees, but in its early years its membership was minuscule and the repression it suffered was fierce. Havel was arrested later that January, and after some 20 interrogation sessions he pledged to concentrate on his “artistic activities” and refrain from “inspiring or organizing collective initiatives or public statements.” Having extracted this promise of good behavior, the regime let him go and, as Havel had suspected, made his promise public. Havel promptly disavowed the promise, but he remained deeply ashamed of his weakness. Zantovsky’s comment on this episode cannot be improved upon:

Havel left prison not only humiliated but also, and perhaps more important, humbled. He realized that for all his determination to resist evil, he was no superhero, but only a frail human being facing forces that might be beyond his power to withstand.

Havel was re-arrested in 1979, and after a show trial he was sentenced to four and a half years in prison. He endured his term with grim determination, as if to expiate his earlier lapse. His Letters to Olga, written from prison to his long-suffering wife, was a painful exercise in self-examination that left him tougher and less tolerant of his failings. To recover his political heroism, he had to say farewell to the parts of his personality that had led him to betrayal. He excoriated

my tendency to trust where inappropriate, my politeness, my silly faith in signs of good intentions on the part of my antagonists, my constant self-doubt, my effort to get along with everyone, my constant need to defend and explain myself.

It was prison that prepared him for power. Upon his release in 1983, his personal life remained chaotic: he resumed affairs with at least two women, one of them the ex-wife of a close friend. But politically, imprisonment validated his moral authority against an ever more bankrupt regime. In his greatest essay, “The Power of the Powerless,” written half a decade earlier, he had given voice, for the first time, to an awareness that power was shifting remorselessly from those with the guns to those with the truth. As Zantovsky writes:

The human capacity to “live in truth,” to reaffirm man’s “authentic identity,” is the nuclear weapon that gives power to the powerless. As soon as the system is no longer able to extract the ritual endorsement from its subjects, its ideological pretensions collapse as the lies they are.

By the 1980s, before Gorbachev and glasnost, Havel sensed his growing authority. When the American Embassy in Prague gave parties, visiting writers such as Kurt Vonnegut, Edward Albee, and Philip Roth sought him out. When Havel ran out of beer at a gathering in his Prague apartment, the cop assigned to surveil him volunteered to go to a nearby pub to refill his jug. This was when he knew that power was flowing his way.

In 1987, when Gorbachev visited Prague, Havel was out walking his dog and happened to see the then–Soviet general secretary waving to the crowd as he left a theater. In an uncanny anticipation of his own experience, Havel imagined what it would be like to be in Gorbachev’s place:

The whole day he sees the unappealing faces of his bodyguards, his schedule is busy with endless briefings, meetings and appearances, he must speak to a vast number of people, remember them all and not confuse them one with another, he must keep saying things that are witty but correct, things that the world, which is ever hungry for sensation, cannot snatch and use against him, he must keep smiling … and he can’t even have a drink after a day like this!

From August 1988 onward, students and police clashed over control of Wenceslas Square. Everyone recognized that Havel was the man of the moment. In the chemical metaphor invoked by a fellow dissident, he acted like carbon, linking with all the elements of the movement to create “a compound of irresistible strength.” After more than 20 years, Havel had long since outgrown the characteristic vices of intellectuals in politics—prolixity and amateurism—and acquired a wily sixth sense about the strengths and weaknesses of his opponents and friends alike.

Six weeks after wondering aloud, in an interview, whether the regime would fall in his lifetime, he was savoring triumph on the balcony in Wenceslas Square in front of hundreds of thousands of his fellow citizens. Here, too, he displayed uncommon heroism. On November 22, 1989, he did not tell those in the euphoric crowd what they wanted to hear. He did not indulge their more bloodthirsty fantasies. He proclaimed instead that their revolution should be different: “Those who have for many years engaged in a violent and bloody vengefulness against their opponents are now afraid of us. They should rest easy. We are not like them.”

“We are not like them” became, for a time, the slogan of the revolution. Even as Romanian revolutionaries were shooting the Ceauşescus, Havel did not allow vengeance to dictate the politics of victory. Though the hated state security organs had infiltrated deep into society, even into the ranks of the dissidents, Havel forbade a witch hunt to root them out. In his first address as president, he sternly told his listeners that they were as corrupt as the regime that had just been overthrown:

The worst thing is that we live in a contaminated moral environment. We fell morally ill because we became used to saying something different from what we thought. We learned not to believe in anything, to ignore each other, to care only about ourselves.

It is rare for a leader to attack the moral illusions of his audience, and rarer still to resist the validating temptations of self-righteousness.

Not all of Havel’s early moves as president were as well advised. He turned out to be a meddling micromanager, fussing over the furniture and curtains in the presidential castle, even the uniforms of the guards. His first trip was not to Bratislava to keep the Slovaks, unwilling partners in the Czech federation, on his side, but to Germany, and before long he went to the United States to bask in the adulation of his foreign friends. Among other tributes, he was given a ceremonial pipe by the chief of an American Indian tribe—and he had the curious idea, on arriving in Moscow to meet Gorbachev, that they should smoke the pipe together. A baffled Gorbachev could only stutter, “But I … I don’t smoke.”

Havel proved an erratic president, farsighted yet distracted by global celebrity. He committed real strategic errors, particularly in his dealings with the Slovaks, who began, under his presidency, to move quickly toward the exit. In July 1992, just five and a half months before the Czechs and Slovaks formally divorced, Havel resigned in a humiliating admission of his failure to keep Masaryk’s Czechoslovakia together.

He might have retired then and there, and used his moral authority to advise and censure from the sidelines, but, convinced that he was still indispensable, he ran again for president and won. The trappings of the office—the cars, the security detail, the presidential plane—had little appeal. The more subtle temptation was existential—the confirmation that he still mattered—as he once confessed:

On the one hand, political power gives you the wonderful opportunity of confirming, all day long, that you really exist, that you have your own undeniable identity, that with every word and deed you are leaving a highly visible mark on the world. Yet within that same political power … lies a terrible danger that while pretending to confirm our existence and our identity, political power will in fact rob us of them.

Here his otherwise courageous lucidity let him down: he appears to have believed that being honest about the temptations of power somehow gave him permission to succumb to them. Once he succumbed, his later terms as president—from 1993 to 2003—were a via dolorosa. His health began to fail. A lifetime of smoking caught up with him. He spent nearly two years in the hospital or recuperating. He stumbled through his duties in what his friends describe as a state of chronic depression and self-doubt, precipitated by recurrent humiliations at the hands of Václav Klaus, the prime minister, his nemesis and successor as president.

Klaus, a “gray zone” economist under the old regime, had joined the dissidents only when the wind seemed to be shifting in their favor. At a high-level meeting in the 1980s, Havel, perhaps suspicious, introduced Klaus as “Dr. Volf.” When they met later, this time as prime minister and president, the elements in their personalities were fatally mismatched. As Zantovsky observes:

In a direct confrontation Havel could not hold his ground against an opponent not burdened by considerations of respect. It was a meeting of two worlds; in Václav Klaus, the advocate of non-political politics met a consummate political animal.

Havel was ill-prepared for the economics of transition, while Klaus wasted little time, selling off state enterprises and privatizing public services in a precipitous embrace of capitalism that left the president deeply alarmed. In one particularly humiliating encounter, Havel pleaded with Klaus to do something to save the jobs of people like Ms. Beranová, who was the manager of Rybárna, his favorite restaurant in Prague. His interventions came to nothing. Poor Ms. Beranová lost her job at Rybárna, which, along with about 23,000 other businesses, was sold off to black marketeers and ex-Communist opportunists. Havel was reduced to giving moralizing speeches to his fellow citizens, begging them to hold on to their ethical compass in the midst of the consumerist and capitalist whirlwind sweeping through the country. Few listened to him, and when he married the young actress after Olga’s death, the Czech tabloids made his life a misery. His jeremiads about living in truth were dismissed with malicious laughter.

Klaus checkmated Havel at every turn in domestic affairs, but in foreign affairs Havel held his ground. He used his prestige to help secure admission for the Czech Republic into NATO and the European Union, thus anchoring his country permanently in the architecture of the West. Havel’s basic geostrategic instincts were sound. He was one of the first to warn that the Putin era “weds the worst of Communism with the worst of capitalism.”

After leaving office in 2003, Havel continued to be hounded by the Czech press and suffered recurring bouts of poor health. Less happy with his new wife than he had hoped to be, and too honest to bask in the remembered glow of his own achievements, he could only mourn his waning reputation. In 2005, he confessed:

I’m running away more and more … from the public, from politics, from people. Perhaps I’m even running away from the woman who saved my life. Above all, I’m probably running away from myself.

His desire to live in truth, no matter how often he betrayed that ideal, was a force that did not leave him, even at the end, when he was matchstick thin, wasted by illness, barely hanging on. “Michael,” he said to his biographer around that time, “I am a ruin.” Still, his lucidity was extraordinary. Late in his life, he remarked that he was moving about his country house, all alone, a battered old man, tidying up, making sure that his table was orderly, all the books piled just so, “fresh flowers in the vases.” Why, he wondered, was he doing this? Or rather, for whom was he doing it?

It’s as though I were constantly expecting someone to visit. But who? … I have only one explanation: I am constantly preparing for the last judgement, for the highest court from which nothing can be hidden.

Havel died at Christmastime in 2011. This complex man, who had the courage to seek a public life, and thus the unforgiving judgment of his fellow citizens, could not have anticipated how they would judge him at the end. They had grown impatient with his presidential lectures. They had derided the failures in his private life. They understood that in politics, Klaus had bested him. But when Havel lay in state, they came by the thousands to pay their respects. It was as if they recognized, in the disillusioning reality of post-Communist life—which unhappily blended the most vulgar aspects and inequities of capitalism with the corruption and conspiracy of Communist political culture—that at least Havel had dreamed of a more uplifting and moral politics. If they had mocked his sermons, if they had not listened, it had not been his fault. Many who were there wept at their loss, as if realizing, once again after a long interval of doubt, how exceptionally lucky their country had been to have him as their all too human president.