Somewhere in Texas, the man who ordered the invasion of Iraq is standing at an easel, painting. He has painted his dogs. He has painted world leaders from memory and from photographs. He has painted himself in the shower and in the bathtub, self-portraits that leaked to the world in 2013 when a Romanian hacker broke into his family’s email. And he has painted, most seriously of all, the faces of ninety-eight wounded veterans of the wars he started, a project he called “Portraits of Courage,” each canvas accompanied by a short biography he wrote himself. There is no stranger second act in the history of the American presidency, and the strangeness is the point, because George W. Bush has spent the years since leaving office quietly becoming something almost nobody predicted: a self-taught oil painter of genuine, if debated, ability, a genial grandfather figure who passes candy to Michelle Obama at state funerals and trades jokes on daytime talk shows.
This is a man who has been underestimated his entire life, and who coined, by accident, the perfect word for it. Campaigning in Arkansas in 2000, he meant to say that his opponents had underestimated him, and what came out instead was that they had “misunderestimated” him, a malapropism so perfectly Bushian that it became one of the defining jokes of his presidency. But the joke contains the truth. He was misunderestimated as the wayward son who would never match his father, misunderestimated as the businessman who lucked into a baseball team, misunderestimated as the lightweight candidate who mangled the language, and misunderestimated, now, as the retired painter dabbing at canvases in his studio. Every time, he turned out to be more than the cartoon, shrewder and more deliberate, which is precisely what made him so consequential and, to roughly half the country, so catastrophic. The Misunderestimated President is the most relatable and least pretentious figure in modern American politics, the guy you’d supposedly want to have a beer with, except that he doesn’t drink, and he presided over the most consequential and divisive decade of the young century. The gap between the goofball and the gravity is the whole story, and the country has never quite figured out how to hold both at once.
The President Paints
The painting began, of all places, with Winston Churchill. After leaving office in 2009, restless and, by his own account, bored, Bush read Churchill’s essay “Painting as a Pastime” and decided to take up the brush, and he did not dabble. He hired a real instructor, a Dallas artist named Gail Norfleet, and announced his ambitions with characteristic swagger, telling her, by his own retelling, that there was “a Rembrandt trapped in this body” and it was her job to liberate him. He worked at it with the same restless energy he brought to everything, cycling through teachers, painting dogs and golf courses and his own feet in the bathtub, until a third instructor gave him the advice that turned a hobby into something more: paint people you know but the world doesn’t. That sent him to the wounded warriors he had met through the bike rides and golf outings his institute ran, and the result was a 2017 book of sixty-six portraits of post-9/11 veterans, a four-panel mural, and prose tributes to each subject, with the proceeds going to his presidential center.
The reception was complicated in exactly the way the Misunderestimated President’s whole second act is complicated. Critics who arrived expecting kitsch found something harder to dismiss; the New Yorker ran a piece calling the works his “painted atonements,” and the paintings of veterans were widely read as a tribute that doubled, whether he intended it or not, as a reckoning with the human cost of his own decisions as commander in chief. Other critics were less charitable, calling the whole enterprise an image-rehabilitation project that painted the American wounded while leaving out the far larger toll abroad. He kept working anyway, producing a 2021 collection of portraits of American immigrants titled “Out of Many, One,” and a gallery of world leaders he had known, rendering Vladimir Putin and Tony Blair and the Dalai Lama in the same earnest, slightly lumpy brushwork he gave his own dogs. The leaked shower self-portraits, dredged up in a hack that also exposed the private digital lives of a sitting political dynasty, made him briefly a punchline, the “bathtub painter.” And yet the work kept getting taken more seriously, the brushwork looser and more confident with each book, and the genial, self-deprecating artist on the book tour, joking that people who thought he couldn’t read were now surprised he could write, became a central exhibit in the slow, strange rehabilitation of his public image that has unfolded across the years since he left Washington.
The Pretzel Incident
On the evening of January 13, 2002, the most powerful man on earth was nearly killed by a snack. Bush was alone in the White House residence, watching an NFL playoff game between Baltimore and Miami, eating pretzels, when one went down wrong. He choked, his heart rate dropped, he briefly lost consciousness, and he fell off the couch onto the floor, where he came to a moment later with an abrasion the size of a half dollar on his left cheek and a bruise on his lower lip. The White House physician explained, with admirable clinical calm, that the president had fainted “due to a temporary decrease in heart rate brought on by swallowing a pretzel,” which is the medical establishment’s way of describing the ancient, involuntary nervous-system reflex that can drop any mammal to the floor when the body decides, briefly, that it has had enough.
The pretzel incident is, on its face, pure slapstick, the commander in chief felled by a Rold Gold while his wife took a phone call in the next room, and the late-night comedians treated it accordingly. The fact that his only witnesses were the family dogs, Barney and Spot, who reportedly regarded him with mild canine concern as he came to on the carpet, only improved the story. But it also slotted perfectly into the developing national portrait of Bush as the accident-prone everyman, the guy things happened to, the president you could imagine choking on a pretzel because you could imagine choking on a pretzel yourself. There was even a faint dynastic echo, since his father had famously fainted and vomited into the lap of the prime minister of Japan a decade earlier, suggesting that sudden public collapses in front of the entire world were simply a Bush family trait. The younger Bush, to his credit, leaned into it, joking that his mother had always told him to chew before swallowing. The bruise faded in a week. The image of a president taken out by a pretzel proved considerably more durable.
Misunderestimated
The malapropisms were their own genre. “Bushisms,” people called them, and they arrived with such regularity that they spawned books, calendars, and a small publishing industry devoted to cataloguing the ways the leader of the free world wrestled the English language to a draw. He worried aloud whether “our children is learning.” He warned that his enemies “never stop thinking about new ways to harm our country and our people, and neither do we.” He observed that “you can’t get fooled again.” And above all he gave the language “misunderestimated,” a word that does not exist but absolutely should, capturing as it does the specific experience of being both underestimated and misjudged at the same time. To his detractors, the Bushisms were proof of a simple thesis: the man was not bright, an accidental president coasting on his family name and a folksy grin, and the malapropisms were evidence of a mind that could not quite assemble a sentence.
But the thesis was a trap, and Bush, on some level, knew it. The verbal stumbles were real, but they coexisted with a cunning political operator who won the governorship of the second-largest state, captured the presidency twice, and ran a disciplined, ruthless campaign organization. The folksy inarticulateness was partly genuine and partly a costume, one that let opponents and pundits dismiss him right up until the moment he beat them, which is the oldest trick in Texas politics. The culture, meanwhile, built an entire satire economy on top of him. Will Ferrell’s impression on Saturday Night Live gave the language “strategery,” a word Bush never actually said but that everyone assumed he had, which is the perfect measure of how completely the cartoon had outrun the man. Comedy Central ran not one but two sitcoms built around mocking him. The jokes were relentless, and they were also, quietly, a gift, because being underestimated is an asset if you are the one doing the winning, and the Misunderestimated President spent a career letting people believe he was the dim one in the room while he counted the votes. Whether the goofiness was the truth of him or a mask over something sharper is a question that has never been fully settled, which is exactly how he seemed to like it.
The Texas Rangers
Before any of it, before the governorship and the presidency and the easel, Bush was a baseball man, and it was baseball that made him rich and famous enough to become everything else. His business career to that point had been a string of underwhelming oil ventures in Midland that mostly lost money, propped up by his family’s name and connections, the kind of résumé that gets a man polite questions from securities regulators about a well-timed stock sale. Then, in 1989, he assembled a group of investors to buy the Texas Rangers, and as the George W. Bush Presidential Library records the pivotal move, he served as the team’s managing general partner for the next five years. The remarkable part is how little of his own money was involved; he put up a borrowed five hundred thousand dollars for a stake of under two percent, while wealthier partners financed the roughly eighty-six-million-dollar purchase. Asked why a man with such a small share was made the public face and managing partner, he answered with disarming honesty: “Because I put the deal together.”
His actual job was mostly to show up. He sat in the stands with the fans rather than a luxury box, handed out baseball cards of himself, learned the names of the ushers, and became, in the process, a recognizable face across Texas, which was rather the point of the whole exercise. He presided over the franchise’s run-of-the-mill years, the era that traded away a young Sammy Sosa before he became a home-run king and signed the aging Nolan Ryan in time to witness his five-thousandth strikeout, and he pushed hard for a new stadium, which the team got through a publicly financed deal and the aggressive use of eminent domain that critics found rather rich for a self-described free-market conservative. When the partners sold the team in 1998, Bush’s borrowed stake turned into roughly fifteen million dollars, a return that transformed his finances and handed him the personal fortune and statewide fame that launched his run for governor. He would later say that the job he might have wanted most in life was commissioner of baseball. He had to settle for president.
The baseball never left him, and it produced one of the genuinely transcendent images of his presidency. Weeks after the September 11 attacks, the Misunderestimated President walked to the mound at Yankee Stadium to throw the ceremonial first pitch before Game 3 of the 2001 World Series, wearing a bulletproof vest under his jacket against the very real threat of assassination, in a wounded city desperate for a sign of normalcy. He climbed onto the rubber, ignored the catcher’s suggestion that he throw from in front of it, and fired a clean strike down the middle as fifty-seven thousand people roared. The former managing partner of the Texas Rangers, the man whose entire pre-political identity had been built in ballparks, delivered the perfect pitch at the precise moment the country needed one, which is the kind of thing that keeps happening with a man everyone insists on underestimating.
The Wayward Son
To be misunderestimated, you have to start out looking like a disappointment, and for a long time George W. Bush obliged. He was the eldest son of a patrician New England political dynasty, grandson of a senator, son of a man who would become president, and for four decades he gave every appearance of being the family’s amiable screwup. He coasted through Yale, where he was better known for running the fraternity party circuit than for the classroom, and through Harvard Business School, served in the Texas Air National Guard during Vietnam in a manner that critics would spend decades questioning, ran for Congress in 1978 and lost, and developed a serious drinking problem that culminated in a 1976 arrest for driving under the influence, a fact kept quiet until the final days of the 2000 campaign, when it nearly cost him the election. He was the charming, aimless heir, the second son of a powerful clan working out his place in the family hierarchy, with no obvious destiny beyond the next drink and a vague sense that he was living in the long shadow of a more accomplished father.
The turn came at forty. The morning after a boozy birthday celebration in 1986, Bush quit drinking, and he never started again, crediting a renewed evangelical Christian faith for pulling him out of a decade-long slide. It is the most genuinely admirable thing about him and the hinge on which his whole story turns: the wayward son disciplined himself, found religion and sobriety, and channeled the same appetites that had nearly wrecked him into politics. He came out of the world of Texas oil and the energy fortunes that shaped his family and his state, a milieu in which the price of a barrel of crude or the security of a strategic resource was simply the air everyone breathed, the same extractive economy that built the modern Sunbelt. Nobody who knew him in his thirties would have bet on what came next, which is, of course, the entire pattern of his life.
The Accidental Election
He reached the White House by the narrowest and most disputed margin in modern history. The 2000 election against Vice President Al Gore came down to Florida, where the count was so close that the outcome of the entire presidency hinged on a few hundred contested ballots, on hanging chads and butterfly ballots and a recount that ground through the courts for thirty-six days. The Supreme Court ultimately halted the Florida recount in the decision known as Bush v. Gore, leaving Bush the winner of the state by some five hundred and thirty-seven votes and, with it, the presidency, even though he had lost the national popular vote to Gore by more than half a million. It was an outcome whose legitimacy a large share of the country never fully accepted, and it meant that the Misunderestimated President arrived in office under a cloud, regarded by his opponents as a usurper installed by the courts rather than chosen by the people.
He governed his first months accordingly, a minority-vote president pushing a modest domestic agenda of tax cuts and education reform, his approval ratings ordinary, his presidency shaping up to be a cautious and unremarkable one. The pundits had him filed away as a caretaker, a one-term placeholder coasting on his name, a man who would be lucky to win reelection. They had, once again, misunderestimated both the man and the moment, because the presidency that history would actually hand him bore no resemblance to the one he was elected to. The cautious domestic president nobody feared was about to become a wartime leader who reshaped the map of the world, and the Misunderestimated President was about to be tested in a way no peacetime résumé could have predicted. Everything changed on a clear Tuesday morning in September.
September 11
On September 11, 2001, nineteen hijackers flew passenger jets into the World Trade Center and the Pentagon and, after a passenger revolt, into a field in Pennsylvania, killing nearly three thousand people in a single morning and ending the long American holiday from history. Bush was reading to schoolchildren in Florida when an aide whispered the news in his ear, and the footage of his face in those seconds, frozen and uncertain, would be argued over for years. But three days later he stood atop the rubble at Ground Zero with a bullhorn and his arm around a retired firefighter, and when the crowd shouted that they could not hear him, he answered that he could hear them, and that the people who knocked these buildings down would hear from all of them soon. It was the finest moment of his presidency, a surge of national unity that pushed his approval rating to ninety percent, nearly the entire country rallying behind a president half of it had refused to recognize ten months earlier.
The man transformed by that morning was no longer the genial baseball owner or the tongue-tied governor. The attacks gave the presidency a singular, consuming purpose, and they gave Bush a clarity and a conviction that admirers called moral courage and critics called dangerous certainty, and which were probably, like most things about him, both at once. The misunderestimated lightweight became a wartime president overnight, and the decisions he made in the following years, made with the absolute confidence of a man who believed he was protecting his country from the next catastrophe, would define his presidency, reshape the world, and divide the country more deeply than anything since Vietnam. The unity of that September did not last. Almost nothing built on the foundation of that day did.
Mission Accomplished
The response to the attacks began with broad support and ended in the longest and most contested chapter of his presidency. The invasion of Afghanistan in late 2001 to topple the Taliban and pursue al-Qaeda commanded near-unanimous backing. The 2003 invasion of Iraq did not, and it became the defining and most disputed act of his time in office. The administration made its case for war on the grounds that Saddam Hussein possessed weapons of mass destruction, including the claim, built into the 2003 State of the Union, that Iraq had sought uranium ore from Africa for a nuclear program, an assertion that rested on documents later shown to be forged. After the invasion, the stockpiles that had justified the entire enterprise were never found, because they did not exist, and the question of how the intelligence had been so wrong, and how much the administration had shaped it to fit a decision already made, remains one of the most bitterly argued questions in American life.
In May 2003, weeks after the invasion, Bush landed a fighter jet on the deck of an aircraft carrier, strode across it in a flight suit, and declared major combat operations over beneath a banner reading “Mission Accomplished.” The war would grind on for nearly eight more years. The banner became the single most enduring emblem of premature triumph in modern politics, a symbol that haunted him as the country slid into a brutal insurgency, as the work of private military contractors and the clandestine machinery of renditions, black sites, and the war on terror drew condemnation around the world, and as the deployment of an entire generation’s military technology failed to produce the swift, clean victory that had been promised. The cost was staggering and is still counted: more than four thousand American troops killed, tens of thousands wounded, and Iraqi deaths estimated in the hundreds of thousands, a toll that no flight suit could ever square. As the Miller Center’s account of his presidency lays out, the war remade the Middle East and the American standing in it, and the argument over whether it was a noble blunder or a catastrophic deception has never been resolved, and may never be. It is the heaviest weight on his record, and he has never disowned the decision.
Heck of a Job
If Iraq was the gravest failure of his presidency, Hurricane Katrina was the one that broke its spell. In late August 2005, the storm overwhelmed the levees protecting New Orleans, the failure of an aging system of flood-control infrastructure drowning much of the city and trapping tens of thousands of people, disproportionately poor and Black, on rooftops and in a fetid convention center for days while the federal response stalled. Roughly eighteen hundred people died. The images of a great American city left to the floodwater while help failed to arrive, and the spectacle of suffering that the wealthiest nation on earth seemed unable to relieve, were a wound to the national self-image that has never fully healed, and they fell, fairly or not, on the president.
Two moments crystallized the disaster around Bush personally. The first was a photograph of him peering down at the flooded city through the window of Air Force One as he flew over rather than landing, an image of detachment that his own aides later recognized as a catastrophic misjudgment. The second was a sentence. Visiting the region, Bush turned to the head of the Federal Emergency Management Agency, an overwhelmed appointee named Michael Brown, and praised him on camera: “Brownie, you’re doing a heck of a job.” Brown resigned days later amid the wreckage of the response, and the phrase entered the language as a byword for cluelessness rewarded, for the gap between an administration’s serene self-assessment and the disaster unfolding in plain view. The unity of September 2001 was, by the autumn of 2005, entirely gone. Bush’s approval ratings began a slide from which they never recovered, and he would leave office among the least popular presidents in the history of polling.
The Goofiest Moments
And yet the human being kept surfacing through the wreckage of the second term, and the unguarded moments accumulated into a portrait that, in hindsight, the country found oddly endearing. There was the day in Baghdad in December 2008 when an Iraqi journalist, in protest, hurled both of his shoes at the president’s head, one after the other, and Bush ducked them with the reflexes of a man who had once played a lot of dodgeball, then quipped to the stunned room that all he could report was that it had been a size ten. There was the time he tried to exit a press conference in China through a locked door, turning back to the cameras with a sheepish grin. There was the unsolicited shoulder rub he gave a visibly startled Angela Merkel at a summit, and the time he nearly fell off a Segway, and the goofy dancing with a drum troupe while waiting for John McCain on a stage. Each one fed the sense of a man fundamentally without pretension, a stream of viral, unguarded human moments that no amount of message discipline could contain.
The rehabilitation accelerated after he left office, and its emblem became a piece of candy. At a 2018 state funeral, cameras caught the former president discreetly passing a cough drop to Michelle Obama, seated beside him, and the small, warm gesture between a Republican and a Democratic first lady went around the world as a symbol of a more civil age that many Americans suddenly missed. The friendship between the two of them, the painting, the gentle talk-show appearances, the studied refusal to attack his successors by name, all of it combined to soften the Misunderestimated President into something like a beloved national grandfather, the goofball uncle of American politics. It helped that the contrast with what came after his party flattered him in retrospect; a certain kind of voter who had loathed him in 2006 found themselves, two decades later, feeling a strange nostalgia for the man who at least seemed to mean well and at least could laugh at himself. Whether this represents genuine grace or a comfortable amnesia about the wars and the dead is, like everything else about him, a matter on which the country cannot agree, and probably never will.
What 2026 Owes the Misunderestimated President
In the long gallery of presidencies and their stranger turns, Bush occupies a peculiar and instructive place, because the distance between how he is remembered and what he actually did is wider than for almost anyone else who held the office. He is the patron saint of the underestimated everyman in American politics, the proof that a folksy, plainspoken, even bumbling persona is not a weakness but a weapon, that letting your opponents think you are the dim one in the room is a strategy as much as an affliction. The whole apparatus of the relatable, anti-elitist, regular-guy candidate, the one you’d want to have a beer with, runs straight through him, and every politician since who has been dismissed as a lightweight and then won anyway is working in a tradition he perfected by accident.
But the deeper lesson is the one the painting keeps trying to tell. Here is a man of genuine personal warmth and real private decency, who beat addiction and loved his country and now spends his days honoring the wounded in oil paint, and who also launched a war on a false premise that killed hundreds of thousands of people and destabilized a region for a generation. Both of those things are true, and the unbearable difficulty of holding them together is the actual subject of his second act, whether he means it to be or not. The veterans he paints are the survivors of his own decisions; the candy he passes to Michelle Obama is offered by the hands that signed the orders. The country’s slow warming toward him is partly a tribute to his decency and partly a failure of memory, and it is not obvious which is winning. The Misunderestimated President turned out, every single time, to be more than the goofball the world took him for, sharper, more deliberate, more consequential, and that was exactly the problem, because the same man who could not say “misunderestimated” correctly could, and did, change the shape of the world. He is still out there painting, and the question of what those paintings are for, atonement or amnesia or simply a restless man filling his days, is the question of his whole presidency in miniature. Perhaps that is the final way he has been misunderestimated, by a culture that would rather remember the pretzel and the candy and the lovable, brush-wielding grandpa than reckon with the consequences of having handed enormous power to a man it never took seriously until it was far too late. The dogs are painted. The veterans are painted. The wars are over, mostly, and the man who started them is in his studio, mixing colors, and the country goes on arguing about whether to forgive him.