Bill de Blasio Has Some Regrets

BROOKLYN, N.Y.—The mayor likes to walk in the middle of the day, preferably around 2:30 p.m. This is the best time, when the sun has traveled across Prospect Park, just beginning its descent west, and when, on weekdays, the shaded trails are empty and still. When most New Yorkers, at home or at work, have someplace else to be.

On Thursday, Bill de Blasio’s city-issued black SUV pulls to the curb. “Can we go get a hot dog?” he asks his staff inside the darkened car. I stand waiting outside. The mayor, nearing his final months in office as the city decides who will replace him in City Hall, has agreed to show off his regular route, a private routine he’s guarded for himself the last year. “If I was doing my walk, I’d go get a hot dog and then go to the restroom,” he tells the staff. Five minutes later, de Blasio is out of the car with his press secretary, a scheduler and a single member of his security detail, all of whom fall back a perfect five paces behind.

“Once we get the hot dog,” he tells me, “I will then take you on the authentic route.”

After walking to 9th Street to acquire the hot dog, we double back two blocks to 11th Street, where he and his wife Chirlane McCray live nearby. “Okay, so you see the proper entry?” he asks. “I go into the 11th Street entrance, because that’s my street. I wouldn’t go to just any entrance. That’s my entrance. We could go through another entrance, but if you want authenticity, we’ll go to 11th Street.”

After the start of the pandemic, this long walk replaced de Blasio’s visits to the YMCA in Park Slope, a neighborhood gym where he has been a member since 1986. The Y became something of a problem: He’d come 11 miles from the mayor’s residence at Gracie Mansion just to “come home.” The papers mocked his workouts as extended stretches. In 2019, when de Blasio made his disastrous run for president, infuriating New Yorkers, police unions regularly protested de Blasio outside the gym. Inside the lobby, anonymous leaflets read, “By entering these premises you agree not to run for president.” When Covid arrived, a deeply anxious city wasn’t entirely thrilled with his replacement activity: The walks appeared self-indulgent and disconnected from the nightmare unfolding around him. The tabloids followed him through the park—“De Blasio goes for aimless strolls as city struggles to get by,” a New York Post headline read—and in the photos de Blasio appears as a solitary figure, hunched and alone, making calls on his cell phone.

If these walks seemed aimless and lost to the outward gaze of his own city, it’s clear as we walk, with de Blasio narrating the route as he goes, that they felt like something else entirely to the mayor himself. But only on the eve of the next mayoral race does he seem more ready to share more of himself, of his enjoyment of the city he governs. Eight years into his tenure, de Blasio has arrived at a moment of clarity about the distance that colored his relationship with New York—that he let “tighten him,” he says—and that, by his own admission, hurt him on the job.

New York is a city of daily rituals, enmeshing its residents’ private moments and memories, the secret history of 8.4 million people, with the public sprawl of an otherwise anonymous city. One of the great mysteries and frustrations of the de Blasio era were the many moments in which New York’s chief executive, the emblem of the city, seemed to resist that emotional connection, when he had as much of it to share as anyone. De Blasio fell in love here, raised his kids here, found a home here, has decades of New York politics under his belt and now talks freely about the “enthralling” lure of a city in recovery. He has his park entrance, his hot dog order (hot sausage with sauerkraut, mustard), the special route he seems proud to show off to a reporter. “All right,” he says, moving to a lane of dirt running parallel to the paved road inside the park. “So now what we specifically do: We go to the dirt. Because it’s nicer to walk on dirt than grass.”

Right away, we pass the baseball diamond where he coached his kids in Little League. The route, usually about three miles long, always leads past the Picnic House at the center of the park, where he and McCray were married in 1994 beneath a tall pin oak tree.

“Every field is a story to me. I have memories all along the way. It’s like we’re humans, who happened at some point to get elected to something? And then that point ends, thanks to God and term limits. And you resume human life,” he says.

“This is where my life played out. Family, marriage, becoming an adult—everything was here. And it’s grounding in a way that’s very particular. If I really want to try to find balance, I could go anywhere, but there’s nothing like doing it here. So that’s why I always did it. I didn’t make it up. It wasn’t like, ‘Oh, let me figure out something really inconvenient to do that people will be pissed off by.’”

He has, over time, developed a number of regular routes: One of his favorites is a walk through Green-Wood Cemetery, where the gravestones go for 478 acres. Another cuts through “some quiet streets” near his house in Park Slope. During the pandemic, he was seen walking alone in Murray Hill, a section of Manhattan filled with college bars, and the image seemed sad and solitary. But his favorite is Prospect Park, the massive public green space bordering at least six neighborhoods in Brooklyn. “It’s very egalitarian,” the mayor says. “It’s never had some of the elitism” of Central Park or Gramercy Park.

As we walk, most people don’t seem to recognize the mayor—his face partially obscured by a Russ & Daughters baseball hat, his 6’5” frame moving fast—or if they do, they stay quiet. As we move to a wooded path, the Bridle Trail, shaded by trees on either side and empty, there is a noticeable distance between the mayor and his people.

“I think what I failed to do was to recognize how important it was to let people into [this experience]. And not, particularly in the tougher times, lose that piece of yourself and fail to show it to people,” he says as we go deeper into the woods. “Because I now realize I had known it intellectually, but I didn’t really get it,” says de Blasio, who was a political strategist before he became a candidate and likened the point to “that thing where you might be really good at giving relationship advice to a friend” but can’t take that advice yourself.

“I think I sort of once was lost and now I’m found. I lived my authentic life a long time. I think this job tightened me too much. Or I let it tighten me. I think I’m going back to who I am. That’s also a joyous moment. It really is. This is how I want to live. This is the right way to live.”

Down the hill, a clearing opens in the woods. Two kids are playing on a fallen tree. Smoke rises from a nearby grill pit where a family is cooking. The path leads out of the trees and back onto the lawn to Prospect Park Lake, a sudden wash of blue up ahead. To the right, across the road, past another stretch of green, about 100 yards away, a father and his young son are playing catch with a miniature football. De Blasio is barely in sight before the father stops, spots the mayor, and yells: “No one wants you! You’re the worst. You’re the WORST!” His son watches in silence. “I CAN’T WAIT FOR YOU TO GET OUT.”

De Blasio turns, as if saying goodbye to a cashier. “Have a nice day!” he says, then plows ahead on the trail.

Halfway down the path, like a kid, de Blasio darts to the left, turning off the dirt into a gap in the woods that steeps upward. The opening is tall and narrow, de Blasio-sized, and his tall frame slides through the leaves. “So you have to—” he gestures, ducking. “Come here!”

“Where are we going, what’s happening,” he says, his voice pitched and suddenly ethereal. He’s the guide in a game. “We’re in a mystical paradise. You turn away and everyone is gone! Come with me to a magical place!” The mayor returns. “I didn’t fully get this piece of the park until the pandemic: these inland trails,” de Blasio says, “I kept walking around and one day I saw it, and I was like, ‘What’s that? I gotta go check that out.’”

“Doesn’t it feel different?” He looks around at the trees.

The mayor, the local press agrees, appears to be finally having fun in his job. He is doing daily morning press conferences that take odd and irreverent turns. He is riding the Cyclone at Coney Island, visiting the top of the Empire State Building, eating on camera, enjoying the city. He is acting, as Slate put it, “lighthearted and weird.” His hang-up, as former aides describe it, about not appearing frivolous has not entirely faded, but something has shifted. The “spring of Bill,” which then became the “summer of Bill,” as his City Hall press shop has packaged it to reporters, is perplexing not only because it took so long, too late to change minds, but because it took so very little to make the change.

“Hey, better late than never,” he told the hosts of HOT 97’s “Ebro In The Morning” last week.

The mayor attributes this new energy in part to the city’s recovery—“It’s like everything about New York City is super concentrated in this moment,” he says—and to the piece of him that has let go. He’s learned to “just be,” he says multiple times as he strides through the forested path, ducking past branches. There are other contributing factors: Gov. Andrew Cuomo, beset by scandal over Covid deaths and sexual harassment, is hovering less over the city and its mayor. And the field of candidates in Tuesday’s mayoral race is so totally “petty” and “lacking in a compelling vision”—his words—that not one of them excites de Blasio enough to lock in his vote until Election Day. (When I suggest that people all but assume he is supporting Eric Adams, the Brooklyn borough president and former cop, de Blasio says, “They can say that all they want.”)

This might be bad for the people of New York City, but de Blasio seems to think it’s good for him, for the sureness of his legacy, for the influence of his voice and, maybe most of all, for his peace of mind.

“Look at last night for God’s sakes. Jesus! That was like bad high school debate. It was just so petty,” he says of the final mayoral debate that aired the night before. “It was like, is this really healthy? Is this really as good as it gets?”

De Blasio traces the perimeter of Prospect Park Lake, the cars from Parkside Avenue visible through the trees, moving from one dirt path to the next, heading north past the boathouse. The next person de Blasio passes, a 30-something guy, spots the mayor from afar and averts his gaze, craning his head to the left as he walks. Another woman passes and does a double take, placing the mayor before walking ahead without comment. Only one person stops de Blasio on his walk that day, a young musician who asks de Blasio about arts and culture in the city.

“I mean, the folks who are corrupt, and the folks who really are not in it to help people, go get ’em. But there’s a lot of decent people. And don’t try and like find things that aren’t there,” de Blasio says, turning the conversation back to himself. “So if my sin is, I go for walks, I’m like, really? Think about that! The thing that makes people upset is [me] going for walks.”

There is, of course, more than the walks: de Blasio spent much of the pandemic in his own petty battles with Cuomo. He frustrated parents with a confusing and shifting plan to reopen public schools. After the killing of George Floyd last summer, former City Hall employees staged a series of major protests outside his office and he is now facing a worrying spike in crime in his final months. One public opinion survey in May showed his approval rating above 50 percent, a rare moment above water still touted by his staff. Recent polls show him well below that figure.

In January, de Blasio and aides had what they now refer to as a “reset” meeting. The mayor, worried about losing his “bully pulpit” during this summer’s mayoral race, said he wanted to re-run the “Tale of Two Cities” campaign that swept him into office in 2013 with a message about rampant inequality after 20 years under Michael Bloomberg and Rudy Giuliani, helping de Blasio build broad support from the Black community. His fear that one of the candidates would run as a viciously anti-de Blasio candidate, as he did with Bloomberg, never played out as sharply as he suspected, nor did, in his view, a candidate emerge with a clear and leading vision. “I think this has been an entirely amorphous election. If they embrace what I did, great. If they don’t, fine,” he says. “The question is: Did the things we started”—his signature issues of universal pre-K and paid sick leave, for example—“did they prove to continue to work and be meaningful, and I think they will. I think they’re going to have a long life, these ideas. And I’m at peace with it.”

To some degree, de Blasio has come to accept New York’s special relationship with its mayors, who function in public life as irrepressible and vivid personalities—figures to like, to dislike, to puzzle over and mock. It seems significant, as a matter of the city’s sensibility, that the next mayor might, for instance, be the city’s first smoker in decades (Kathryn Garcia) or a man who, as a means of self-critique, writes journal entries in the third person (Eric Adams). “This strange animal that is being mayor of New York, it is unlike anything else. I’ve worked with mayors around the country,” he says. “They come up to me and are like, ‘I can’t believe what’s going on, or that that’s happening to you.’ I mean, it’s almost like a sympathy line at every meeting to say: ‘What is going on?’”

Often during his time as mayor, that constant razor’s edge between love and hate, enthralling and impossible, seemed to annoy rather than enamor its mayor. Today it seems to delight him. There is a story he tells about a city council meeting to debate a proposed bike lane on 11th Street in Park Slope. De Blasio supported it, and one of the “old timers,” who didn’t, stood up in the meeting. “He points at me accusatory and says, ‘You don’t know what it’s like on 9th Street!’ I’m like, ‘Dude, I live two blocks from you, I really feel like I do know what it’s like on 9th Street!’”

“It was like I was from an entirely different nationality. I mean, he just thundered, ‘You! You! You interloper!’ It was fabulous!” he says.

A former City Hall staffer recently described Bill de Blasio’s mayoralty as an encapsulation of the human condition, which is less grand than it sounds. “The pendulum was always swinging,” the person said. “There were days when he was confident and days when he was riddled with self-doubt. There were days he felt he really embodied what New York City needed in a mayor. And there were days when he lost that.”

In 2013, during the first campaign, when de Blasio was at the bottom of the polls and free from the burden of expectations—“We were lovable losers,” he says—Bill Clinton called him one day after seeing a front-page photo of the candidate and his family dancing at a parade: “‘I saw the photo in the New York Times.’” De Blasio drops into a Clinton impression. “‘And you guys look like you’re having so much fun out there. That’s what people want from a candidate.’”

“He’s one of the great masters. You think I would have written it down,” the mayor says. “I think I heard it, but I didn’t take it in.”

“We are coming into the home stretch,” he says. “I’m giving you a warning. We will end at the stump.” It’s an hour and 15 minutes into the walk and de Blasio has covered 2.53 miles.

The official story of the stump, according to the New York City Parks Department’s forestry director, is that a large pin oak got sick and had to be felled at the height of the pandemic. The Parks Department suspected oak wilt disease, bacterial leaf scorch and symptoms of a disease called Hypoxylon canker. They tried to save the tree, but couldn’t, and it came down last August.

It was on one of his walks that de Blasio discovered what happened to the tree where he and McCray had their wedding.

“There was a tree,” he says. “It’s part of a tree now. I went one day in the middle of Covid and everything was horrible and I’m walking by my tree for solace and my tree’s not there anymore!” he says. “Recalling the great line from Chrissie Hynde and The Pretenders: ‘I went back to Ohio and my city was gone.’”

Navigating now to the marriage stump, the mayor takes a left off the main drag, turning into a densely wooded ravine billed by the Park Alliance as New York City’s “last forest.” We head down one trail, another left, then right, then up a steep path, then left again. A trace of sweat gathers on de Blasio’s temple as we emerge from the woods onto a rolling expanse of green leading to the Picnic House at the center of the park.

Even from a distance, the stump is huge. Multiple kids are playing on top of it. It measures five feet across.

The day de Blasio discovered the tree was gone, he called Chirlane from his walk. “It was like one of those weeks when things were going wrong and everything. We were still far from out of Covid. I said, ‘I gotta brace you for this.’” He didn’t want her to see it without warning. “She’s a very sane, mature person. But she was sad.’”

He gestured to the kids playing on the stump, the family picnics.

“But everything else is still here,” he says.