Finding the Light

A decade after “Hope and Change” — and a Pulitzer Prize — photojournalist Damon Winter ’97 feels freer than ever before.

A photo of photojournalist Damon Winter ’97


What do you do after “Hope and Change” gives way to fear and loathing?

For photojournalist Damon Winter ’97, the question wasn’t just political; it went to the core of his life and work. After joining The New York Times in 2007, where he quickly earned a reputation for marrying expert technique with vivid storytelling, Winter went on the road with candidate Barack Obama ’83 and brought home the 2009 Pulitzer Prize for feature photography. His indelible campaign pictures — of Obama pointing at a cloud, or greeting ecstatic children or addressing thousands as rain, sweat and tears coursed down his face — immortalized that season of light for the paper of record.

Ten years later, having covered Obama’s more earthbound reelection run, war in Afghanistan, devastation in Haiti and the 2016 campaign of Donald Trump, Winter would be forgiven for feeling sentimental about those earlier, sunnier days. But he doesn’t. When he revisits the photos that made his career, he sees work that is “naïve” and “simplistic.” In the years that followed, he says, “I felt like I had a little more to say.”

The moment that really made him reassess his earlier work shouldn’t surprise anyone who follows the news. The election of a President who doubled as Media Basher-in-Chief led the press to ask itself hard questions: What had they missed about the American voter? How could they defend themselves while remaining above the fray? How could they maintain an objective posture when so much of what the government was saying was objectively false? The dilemma was not limited to writers. We like to say the camera doesn’t lie, but that doesn’t mean it has no point of view. Photographers were no more immune to the jeers of MAGA crowds or the candidate himself than the rest of the press pack. Having borne it for months, Winter emerged from 2016 with “this feeling of futility” that he couldn’t shake.

Ultimately, that feeling has hardened him against nostalgia; it’s also left him freer to say more with his cameras than he’d ever thought possible. He’s traveled a journey parallel to his readers — witnessing Obama’s disillusionment, war and climate crisis, and a President who personifies chaos. Like many of us, including the newspaper nicknamed the “Gray Lady,” he’s become a digital native, a multimedia creator. He’s also grown more forthright about his opinions — especially during the past year, as the first in-house photographer for the Times’s Opinion section. He’s looking toward 2020 with a mixture of excitement and dread and, as ever, an exceptionally keen eye.

Winter’s home on the Upper West Side, which he shares with his longtime partner, photographer Béatrice de Géa, and their son, Noa, is a prewar duplex that Winter is slowly converting into a light-flooded haven of sliding doors and slatted wood. Oddly, only one photo is on display, in the bathroom. “Béa doesn’t want to have to look at the same photos every single day,” Winter explains, while scanning his vast portfolio on a laptop.

It may be de Géa’s preference, but the lack of work on display suits Winter’s reticence — a trait not normally associated with photojournalists (one colleague calls him “a silent assassin”). He started shooting pictures as an undergrad with a camera his mother gave him for his birthday, and fell instantly in love. He’d had an interest in environmental science, but says he’s never fit into any field or clique: “It’s a sort of personal feeling that I’m an outsider.” On our first meeting, he’d apologized in advance for being an uninteresting subject, and here in his home, he seems reluctant to pick his favorite photos, which was kind of the point of the visit.

Winter even casts his success as a lucky break. “It really is the beauty of photography that initially drew me to it,” he says. But “I don’t think I’m creative or crazy enough to live off the wiles of my own mind … I was just extremely lucky to have stumbled into photojournalism.” After the College, he worked at the Dallas Morning News and other papers before landing at the Los Angeles Times, where he was a Pulitzer finalist in 2005 for a photo essay on victims of sexual abuse in Alaska.

Two years later, The New York Times poached him, as part of a larger drive to give the paper more visual flair. “He has a real vision,” says New York Times deputy picture editor Beth Flynn. “When you look at an image made by Damon, it has all the elements that an image should have — light, composition — but it has the Damon Winter vision attached to it.” After he won the Pulitzer, he drew intensive feature assignments around the world.

Winter was up for those adventures — most of the time. In his living room, he shows me a picture of troops evacuating a gravely injured soldier in Afghanistan; a helicopter downdraft throws sepia-toned dust over stoic soldiers, recalling iconic war photos like the Iwo Jima flag planting. Winter had had to walk through a minefield, and saw a tech lose his legs — knowing he might be next. “This is before I had Noa and realized it wasn’t worth it,” he says.

But after dodging mines on the battlefield, Winter caught flak from his peers. In order to capture the intimacy of life on the base, he took some pictures with a phone and a Hipstamatic filter (the precursor to Instagram), breaking Times precedent against digital tweaks. He addressed the backlash from purists in a long post on the paper’s Lens blog, arguing that it was the right tool for the job. “We are being naïve,” he wrote, “if we think aesthetics do not play an important role in the way photojournalists tell a story. We are not walking photocopiers. We are storytellers.”

In 2010, Winter spent many months visiting Haiti after its catastrophic earthquake, working on a series of stories that allowed the Times to transcend the grief tourism typical of disaster coverage. He sought “a way for people to connect, not just to be shocked or to get information, but to feel empathy for people who have gone through something really horrific.” Some of his work captures the carnage and raw grief, but his favorite picture is of a girl walking uphill in silhouette, a full water-cooler jug on her head. It’s not about mourning or poverty, but the Sisyphean task of recovery. “I felt like a different person when I came back,” Winter says. “I felt like I had done something worthwhile.”

“We are being naïve if we think aesthetics do not play
an important role in the way photojournalists tell a story.
We are not walking photocopiers. We are storytellers.”

By comparison, the next campaign was anticlimactic. The tone of Obama’s 2012 run was typified by a photo rich with subtext, in which the President speaks to a crowd: The glass of the teleprompter in front of him reflects an arrangement of flowers, while up in the sky — in the real world — storm clouds gather. After Winter compiled his coverage into a photo essay headlined “A Face More Careworn, a Crowd Less Joyful,” White House press secretary Jay Carney complained to a colleague of Winter’s: “Who the fuck is Damon Winter and why is he such a terrible writer?” Winter laughed it off. “It reinforced the fact that I was never his photographer,” he says.

Winter’s next campaign made the skirmishes of 2012 seem quaint. Discussing assignments in 2015, he’d told photo editor Jessica Dimson he wanted to cover Trump. “I think he was interested in the challenge,” says Dimson. “Nobody knew what kind of campaign it would be.” One of Winter’s colleagues, Times White House photographer Douglas Mills, believes he just knew a rich subject when he saw one. “Barack Obama was the most photogenic President,” says Mills, “but Donald Trump is the most iconic.”

Consider one of Winter’s most memorable shots (below): Trump stands in front of a murky American flag, every part of him obscured except a shock of that strange hair and a brightly lit hand pointing like a raised gun. Winter had been trapped for hours behind barricades along with dozens of other journalists, heckled by the crowd and ignored by hostile staff. “You’re stuck in this pen,” Winter says, “and you have time to really contemplate: ‘What is it that I want to say? What can I do within the confines of this situation?’” This particular situation was both more confined and more chaotic than usual, but the constraints worked to Winter’s advantage. He saw a fuzzy shadow — probably another reporter’s phone — obscuring most of Trump’s face, and started clicking and adjusting, knowing not only what the perfect picture would look like, but also what it would convey: “These sort of iconic big grand gestures that he makes, and his iconic hair — but there was nothing underneath.”

It was the kind of work that made even seasoned Washington photojournalists ask themselves, How’d he do that? “He just sees things differently,” says Mills. “Everyone is looking for the right face, but Damon found a spot in the light, and turned a well-lit photograph into a silhouette.” Mills is on a text chain with photojournalists, and the day before he spoke to me, one of them had linked to a Winter photo of Mitch McConnell and captioned it, “DAMON. AGAIN.”

For all the groundbreaking work, covering Trump took a psychic toll on Winter. De Géa noticed a shift in her partner’s moods; on his rare visits home from the trail, she told him he had the same “PTSD look” in his eyes he’d had after Afghanistan. “I would be angry and impatient,” Winter recalls. “You’re being mistreated by the people running the campaign, by the supporters and then by the candidate, and witnessing this shift in the mood in the country that you didn’t really understand … At least in Afghanistan there were long lulls in between the really intense stuff.”

He stuck with it, literally, to the bitter end. Winter’s favorite photo from the campaign was one of his last. On election night, Trump campaign staffers, never expecting to actually win, got precipitously drunk. Around 4 a.m., a woman cut her bare foot on the shard of a wine glass, leaving a trail of blood on a MAKE AMERICA GREAT AGAIN poster. Winter started shooting the poster, and staffers berated him. “I said something back, like, ‘This is a really important picture,’” he says, laughing. “I felt like it really told the story of what had happened that night and what was to come.” In the end, it never ran. “The editors thought it was too provocative.”

It wasn’t just the existential crisis of the new administration that left Winter feeling adrift in 2017. The Times photo department was also going through a shakeup, which temporarily left staff photographers unsure of their beats and assignments. “It was easy to get lost in the shuffle,” Winter says. But then, in 2018, some good luck came his way. The Opinion Page had been looking to expand its online presence, and one idea was to assign a dedicated staff photographer to give it a coherent style and exclusive material. Winter’s photo essays were already straying into editorial waters, so why not loan him out?

The timing was perfect, not just for Winter but also for a paper trying to keep pace with the world. Old-school editorial pages, with their godlike tone and throwaway photos, could never compete in an online ecosystem of hot takes and visual flash. In order to build digital subscriptions after years of giving away content, newspapers have been forced to both grab browsers’ attention and earn their loyalty by distinguishing themselves from clickbait. Winter’s dynamic photography is leading the way on both fronts.

Winter’s first Opinion assignment was “sort of right up my alley,” he says — an eye-catching series of double-exposed portraits of transgender people, their bodies superimposed with artifacts of their lives. This kind of impressionistic trickery was “so different from what we generally do for a newspaper,” he says. Another creative foray was an essay about a perpetually flooded North Carolina town. Looking at his photos, it takes a minute to realize that every single one is a reflection — an underwater image of buildings or streets shot through stagnant floodwaters and flipped over. It was uncharted territory both aesthetically and thematically: art in the op-ed pages.

Shooting photos to accompany opinion pieces also meant grappling with writers’ points of view. Sometimes Winter was fully aligned with them; other times he layered on his own take. He’s done both while working with the somewhat controversial writer Bari Weiss ’07. Last year, he shot portraits for Weiss’s piece on a group of right-leaning iconoclasts who make up the so-called “Intellectual Dark Web.” He lit them dramatically in deep twilight, often in pompous poses, poking a bit of fun at their self-importance. “[Weiss] will probably hate me for saying this,” Winter says, “but I kind of wanted it to be a little bit of a check and a balance.”

Yet he and Weiss connected deeply on a truly dark assignment — covering the October 2018 mass shooting at the Pittsburgh synagogue Weiss had grown up attending. They tried to gain entry to the crime scene, to witness and convey what really happened inside. “I’d been thinking a lot about the way mass shootings are covered,” says Winter. “We have become so numbed by the rote imagery” — the antiseptic flowers and tears papering over the murder of innocents. They were denied access, so Winter chose to heighten the banality, making note of “this orchestrated dance that follows these horrific acts of gun violence,” inuring us to a scourge we keep on doing nothing about.

Winter has kept up a frantic travel schedule, even if his assignments are less dangerous and more contemplative than they used to be. When we met at his house, he’d just come back from several days in Hawaii, shooting 70 portraits of multiracial people for a story. Another recent shoot was for a piece titled “The Lessons of a Hideous Forest,” about the flora growing over Staten Island’s infamous Fresh Kills landfill. The pictures, juxtaposing strangling vines with relics of trash, were twisted and eerily beautiful. Their careful composition and abundant shadows were recognizably Damon.

“The whole dark thing — it’s not particular to Trump’s campaign,” Winter says. “I’m an equal opportunity offender.” It seems doubly strange, then, that his colleagues so often talk about how talented he is at “finding the light.” What does he make of the seeming contradiction?

“I’ve never been a fan of that National Geographic golden hour light,” he says. “It’s just kind of uniform and syrupy sweet.” He prefers the constraints of a darkening sky, sometimes even the flickering fluorescents of an auditorium. “You can find beautiful, interesting light in lots of different places.”