Dan Doctoroff, Sidewalk Labs CEO, Reckons With His Legacy

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On the day I meet Dan Doctoroff, I walk across Manhattan from the Shed, which he created, to the East River Esplanade, which he planned; catch a ferry, which he launched; get off at the Long Island City waterfront, which he reclaimed from industrial neglect; and enter a café overlooking Hunters Point South Park, where he once envisioned an Olympic Village. Eventually, I leave him by Citi Bike, which he dreamed up.

Those verbs are a shorthand, of course. He didn’t create, plan, launch, reclaim, envision, or dream up anything single-handedly. His role as deputy mayor for economic development and rebuilding in the Bloomberg administration was to adopt ideas (some his, many not), convince others that they were feasible and good, then maneuver those fantasies into reality. Even so, it would be hard to spend a day moving around New York and not encounter at least one item on his long list of urban accomplishments. Every time someone sees a show at the Whitney, scans a brain in Columbia’s Greene Science Center, runs a mile at the Ocean Breeze Athletic Complex on Staten Island, buys a saw at the Home Depot in Bronx Terminal Market, watches the Mets play at Citi Field, commutes by subway to Hudson Yards, boards a ferry to Governors Island, or watches the sunset from Brooklyn Bridge Park, that person is animating parts of the city that once existed only as documents on Doctoroff’s desk. His stint in government lasted from 2002 to 2008, surely among the most consequential half-dozen years of any city builder’s term in New York history. He wasn’t, as some have claimed, the 21st-century Robert Moses; he was Moses in a hurry.

Doctoroff was a 43-year-old finance guy with abundant self-confidence but zero experience in public service when he stepped into the second-most-powerful job in city government on January 1, 2002. He quickly developed a reputation for relentlessness. “He was a hard-charging guy who thought nothing of calling your cell phone at 2 a.m.,” recalls the architect Vishaan Chakrabarti, who was the Manhattan director of city planning during the Bloomberg years. He also had a temper. “He’d blow up 15 minutes into any meeting.” He argued with opponents, cajoled skeptics, shouted at staff, and recruited supporters to his vision of a future New York, which seemed obvious and urgent to him but infinitely postponable to many. The enemy was inertia, a toxic substance that asphyxiates good ideas. “We set deadlines, and I pushed,” Doctoroff acknowledges. “I pushed aggressively.”

Few people in government knew that Doctoroff’s father was dying from ALS. A few years later, his uncle was diagnosed as well, and he died in 2010. Both men had inherited a genetic predisposition to it; at the time, Doctoroff declined to have himself tested for that mutation. Then, in October 2021, he himself was diagnosed. Doctoroff has now set a goal of raising $250 million for Target ALS, the research foundation he co-founded after his uncle’s diagnosis. “Nobody’s ever raised that much money for ALS before,” he says with obvious pride.

Some symptoms of the disease are evident. The notoriously smooth talker enunciates more slowly than he used to, pauses for breath, and can walk only short distances with a brace on his right leg and hiking poles in his hands. He’s had to relearn his changing body, and when we leave the café, he pushes up from the table and propels himself to a waiting car like someone who has practiced a tricky maneuver until he knows he can nail it in public. He fends off pity with an anti-pathos shield of good cheer. Yet for someone who plotted out his own life and New York’s trajectory in multi-decade chunks, coping with a short time horizon has meant redefining the principle that shaped him: the future. “That was my dominant approach to life. I thought about it so much that I never enjoyed any accomplishment because I was on to the next thing.”

New York was in crisis when Doctoroff took office, and it is again now. The post-COVID city is still struggling with a dormant midtown, plummeting tax revenue from commercial real estate, a flood of migrants who have overwhelmed the shelter system, a housing drought, a retreating tech sector, soaring rates of fatal overdoses, and a magma of rage that regularly bursts through the crust of civilized mutuality. When Eric Adams and Kathy Hochul needed a strategy for coping with that pileup, Doctoroff was tapped to help formulate it along with Richard Buery, CEO of the Robin Hood Foundation and deputy mayor under Bill de Blasio. The result was New New York, a detailed survey of where people still walk, work, and shop in pre-pandemic numbers (everywhere except midtown and lower Manhattan), plus a litany of wishful thinking and small-bore items. It’s an action plan that might turn into actual action if only Doctoroff were available to carry it out.

New York teems with smart, well-connected, civic-minded people with ideas for improving the city. Few of them, though, have Doctoroff’s talent for hurling himself at apparently immovable walls. For all the visionary talk, New York usually opts for the status quo until some crisis or other — a cholera epidemic, a terrorist attack, economic calamity — obliges it to adapt. Expediency rules. Doctoroff was different: From the time he turned his attention to the urban machine, nothing he did was easy. Consequently, he’s had plenty of experience of failure. When I ask what prompted him to keep taking the path of greatest resistance, he tells me he never thought to wonder about that until he went into therapy a few years ago: “I started remembering conversations that I wasn’t meant to hear between my parents, and my mother badgering my father about not being ambitious enough.” (She had exacting standards: Her husband was chief judge of the Michigan Court of Appeals.) “I realized that I didn’t want to disappoint my mother the way my father had. The major motivating force of my entire adult life, and I wasn’t even aware of it.”

The other motivating force was what he saw happening to cities, especially Detroit during his childhood nearby. Ask Doctoroff about it, and he fleshes out that grim history not in vivid anecdotes but in his preferred language of numbers. “When I was born, there were 1.85 million people in Detroit. Today there’s maybe 650,000. New York, same thing. In one decade, we lost 800,000 people, services declined, the subway was eviscerated, crime spiked, and more people left. It took us 25 years to get those people back.”

It took him a while to find his career groove. After Harvard and the University of Chicago Law School, Doctoroff drifted into a finance job to which he devoted more energy than heart. He got married; he and his wife of 40 years, Alisa, have three children. The moment that jolted him out of his lucrative rut has acquired the status of an origin myth. Though it eventually led to his most visible failure, he still relishes telling the story of how a friend dragged him to the 1994 World Cup semifinals between Bulgaria and Italy at the Meadowlands. “I had no interest in soccer or in either team, but I walked into the stadium and it was the most amazing event I’d ever seen,” he says. “I said to myself, Why has New York, the most international city in the world, never hosted the most international event in the world? The Olympics!” Doctoroff had no experience in international sports, urban management, transportation, event planning, or anything even tangentially related to the issue. But he did have money, connections, a sudden passion, and a limitless capacity for homework. While still working full time at the private-equity firm Oak Hill, he spent evenings and weekends learning everything he could about the Games, cities, real estate, and their zones of overlap. He eventually set his sights on the 2012 Games. He teamed up with Jay Kriegel, a political insider who’d come out of the Lindsay administration, and Alexander Garvin, a longtime Yale professor and sage of New York urbanism, and gave himself a crash course in the history of a city he had once detested. (His rare youthful visits made him “feel small and insignificant,” he recalls.) Doctoroff and Garvin roamed the five boroughs hunting for depressed waterfront locations that could be pressed into service for a stadium, an athletes’ village, and all the other infrastructure the Games would require.

At bottom, though, he saw the Games as a means, not an end. “I saw that cities had used the Olympics to get done things that they had been talking about for decades or sometimes generations,” Doctoroff says. He narrates this period in the mid-1990s like an old soldier telling war stories: how, meeting by meeting, he gradually ratcheted up enthusiasm until rooms full of men in suits roared. “They were blown away,” he says of his very first sales pitch. “It was amazing. I got a standing ovation.” Then, in the fall of 2001, just seven weeks after 9/11, Michael Bloomberg won an election for mayor that virtually everyone else thought he would lose and asked Doctoroff to be his right-hand man. Doctoroff declined. Bloomberg asked again, and again Doctoroff turned him down, until his old Lehman Brothers boss and longtime mentor Peter Solomon sent him an eight-page handwritten letter urging him to say “yes” and pointing out that taking the job would add power to zeal in his quest to land the Olympics.

Doctoroff’s years of renegade planning meant that the new mayor could walk into office with a fully formed vision for the future of the physical city. With or without the Olympics, Bloomberg saw that there could be a gleaming waterfront laced with parks, bright new towers going up in business districts that would be sprinkled around the city to ease the rush-hour commute, and grander university campuses bristling with new biotech-research centers.

The destruction of the World Trade Center focused the public’s attention on city building. Suddenly, New Yorkers who had been content to chime in only after the wrapping came off a new tower were poring over master plans and debating the merits of the superblock. It also empowered the mayor — and his No. 1 deputy — to go on an emergency footing and argue that the city’s best defense against catastrophe was grand ambition.

Once at City Hall, Doctoroff stormed out of the gate, trying to run his Olympic dream and the administration’s long-term goals in sync. The procedural grind to keep New York’s candidacy in play — rezonings, land acquisitions, environmental cleanup of toxic sites, funding planning for transit links, and an endless gauntlet of approvals — had to begin immediately. City Council members would have to be wooed or strong-armed, opponents placated. He led with the manic intensity of a Wall Street boiler room, mixed with a burning sense of mission and impatience with hurt feelings.

It was always difficult to separate Doctoroff’s ideas from his personality. Those who opposed him found him high-handed and arrogant; those who joined him thought he was flexible and forward looking. “I was prepared not to like Dan at all,” the urbanist scholar Richard Florida says. “My image of him was a Machiavelli in a suit. When I met him, though, I thought, I really like this guy. He’s smart, and he cares about cities. Dan was two steps ahead of his time. When you look at his quote-unquote failures, they’re because he was pushing too much and too far.”

That approach also yielded a fresh crop of enemies, most prominently Sheldon Silver, the Godfather-like Speaker of the State Assembly. Silver loathed Doctoroff and objected to any project that might draw money and glory away from his Lower East Side district (or himself). He tanked the West Side stadium proposal weeks before the International Olympic Committee vote on the 2012 Games. (Doctoroff hurriedly shifted the site to Flushing.) He blocked the MTA from paying for so much as a turnstile in the extension of the No. 7 subway line. (Doctoroff came up with an independent way to fund it with projected taxes.) Silver quashed congestion pricing for a long time too. (Only after he was convicted on federal corruption charges and driven out of office did it pass the State Legislature; Silver died in prison in 2022.)

Doctoroff’s focus on targets and trend lines could make the lives of actual New Yorkers seem like irksome anecdotes or irrelevant outliers. In communities such as the South Bronx that were both dependent on and suspicious of government, he and his staff came off as only pro forma listeners. Majora Carter, a MacArthur fellow and the founder of the organization Sustainable South Bronx, perceived him as elusive and dismissive. “He came to visit the neighborhood and didn’t even talk to us. That was rude,” she says. Carter recalls Doctoroff’s team as tone-deaf, especially when she asked for the city’s support in creating Hunts Point Riverside Park. “They said they wouldn’t do it because we didn’t have a maintenance plan the way that the High Line and Central Park Conservancy did. I was just like, ‘You expect that from one of the poorest congressional districts in the country? You want me to go to the bodegas and the auto-parts stores and get a conservancy done?’”

Doctoroff insists that his diagnosis has changed him. “I’m more patient, more present, probably a bit nicer.” But he suspects that today’s mellower version of himself might have been a less effective executive. “I don’t think we could have done what we did if I had been the way I am today.”

The ailing Doctoroff occasionally sounds like his younger self. He still uses aggressive as a term of praise and fires off figures archived in his brain (the number of city employees at the beginning of the Bloomberg administration: 314,000. At the end: 298,000). A conversation with him can feel like chatting with a TED Talk. The cascade of bullet points and smiling asides, building up to an inevitable conclusion — it all presents you with the binary choice of responding “Of course!” or “Wait, but …” He’s constantly making his case, striving to win interlocutors over through some combination of charm, insistence, logic, and data — always the data. He has weighed every objection, and — disconcertingly for an interviewer — he’s already formulated his response before I can even ask the question. Does he have any regrets? Has he reconsidered any of his Bloomberg-era priorities? He nods. “We could have focused more aggressively on things like child care and minority-owned businesses. We could have been more aggressive in thinking about how to finance entrepreneurs from disadvantaged communities.” He adds in a follow-up email, “My biggest regret is not being more aggressive in building more housing.” But, he implies, acknowledging a mistake doesn’t mean he was seriously wrong. He pivots as always into justifications and exceptions — credit markets! — and lands on an analysis in which, as anti-gentrification progressives acquired more power and stopped more projects, “the city lost faith in growth.”

In July 2005, the IOC awarded the 2012 Games to London, an outcome that many New Yorkers shrugged off and Bloomberg’s political opponents cheered. The New York Times’ Jim Rutenberg described the mission as “embarrassing” and “quixotic,” a “dead-end” folly that the mayor insisted perversely on selling as a triumph. Doctoroff set a fresh deadline: Earth Day 2007, when the Bloomberg administration would announce its comprehensive strategy for the next 25 years. (Bloomberg would have to win reelection first, but that was a minor obstacle.) This time, the catalyst was a vivid statistical projection. Demographers estimated that New York’s population could hit 9 million by 2030; Doctoroff wanted to be ready. That impetus crystallized into PlaNYC, a shopping list of transformations united by Doctoroff’s philosophy of growth and supercharged by the fresh realization that the virtuous cycle must also be green.

Dense cities like New York are environmentally both good and bad: Apartment dwellers who commute by public transit consume much less energy per person than suburbanites who have large houses to heat and cool and run errands by SUV. Cumulatively, though, cities churn out vast quantities of greenhouse gases. To Bloomberg and Doctoroff, this contradiction meant that cities had an outsize role to play in combating climate change. Rather than simply wait for sclerotic national governments to regulate polluters and subsidize wind-turbine manufacturers, New York could move more nimbly and with greater immediate effect. PlaNYC rested on a new principle: All sustainability is local.

“The two things that made Dan most successful were that he had a program for the entirety of the city and that he looked at it holistically,” says the developer Jed Walentas. In the new regime, sustainability got linked to density and affordable housing, which brought bike lanes, street trees, waterfront access, and outdoor seating. Private interests had to pitch in to enrich the public realm. Still, the suspicion has always lurked that Doctoroff had the clout to demand — and obtain — many more public benefits from developers who stood to make fortunes from his nod.

The Bloomberg administration is easy to caricature as a club of petulant and self-regarding overachievers who left the city shiny on top, rotten below, and overpriced throughout. It was criticized for tossing the keys to developers and corporations in a neoliberal power grab, even though, like a gang of old-fashioned lefties, it also hugely increased government spending. It was attacked for caring only about Manhattan, although its planning was vastly broader in sweep and scope. Critics complained that it was building a city for out-of-towners, when Doctoroff saw visitors as a renewable resource, a way to fund libraries and schools. (“What is tourism?” asks Walentas. “It’s people who work 50 weeks a year, then put all their money in a bag, come here, and throw it in the air. Then they go home without consuming health care or education or anything. It’s the greatest return on investment you could ask for.”) De Blasio ran against the caricature and peddled it for years, even as his administration expanded policies he inherited. Nilda Mesa, a Columbia professor who acted as the de Blasio administration’s sustainability expert, says that her predecessors’ shortcomings laid the groundwork for later success. “They were ambitious, but it was too new, so they’d get pushback and have to drop back. By the time we came in, there was less resistance, so we could take some of the stuff they couldn’t complete and propose it again.”

Doctoroff had some good failures (the West Side stadium), bad successes (Hudson Yards), and partial accomplishments. Rezoning Downtown Brooklyn did not produce the new office district that he insisted New York needed in order to compete. It did create a high-rise residential neighborhood but whiffed the opportunity to include abundant affordable housing. Doctoroff was also on the right side in some of the biggest battles he lost. If he had been able to pilot congestion pricing through a recalcitrant Assembly, today’s MTA would be in better fiscal shape and Manhattan traffic would be lighter.

It’s illuminating to read the coverage from the time and see how regularly Doctoroff was hammered for moving too slowly. “When the economy was burning white hot, as it did for several years, the mayor’s plan appeared to be bold and forward-looking,” the Times reported in 2009, when the city was starting to stagger back from the financial crisis. “But that vitality is missing in some sections of New York today, where developments spurred in part by easy credit and in part by city initiatives are now stalled or in danger of collapse.” The article was accompanied by a photo of a waterlogged construction site at City Point in Brooklyn. Today, it contains more than 1,000 apartments.

In early 2007, Doctoroff gave a speech to mark the Museum of the City of New York’s exhibition “Robert Moses and the Modern City.” By that point, both critics and admirers had anointed him the new Moses, and by speaking there, he was courting the comparison. You can detect a trace of envy in his declaration that “the degree of difficulty in completing a public project is a mathematical function of the number of governmental entities involved,” an idea he called Doctoroff’s Law. He added a corollary: “The chance of getting something done is a function of the length of time from conception to construction.” Unite those two principles, and you get the twin desiderata of the urban technocrat, agility and control. In the speech, he wrestled to balance the urge to move fast (by city-building standards, anyway) with a post-Moses democratic reality. He quoted Moses’s retort to Robert Caro’s The Power Broker: “The cities and second-guessers say we were sometimes rude, arbitrary, and high-handed. Maybe so, but suppose we had waited?”

Doctoroff must have been tempted to borrow that line often in the years since he gave that talk. He still thinks the city could use a little more Doctorovian whip cracking. “My experience in government is that anything temporary is permanent unless you act aggressively to change things. Look at restaurant sheds: They were great, yet here we are three years later and we haven’t been able to pass legislation to replace them with more flexible structures that are beautiful and can serve multiple purposes. Which is what we should do.”

In 2008, he bowed out of the Bloomberg administration and into Bloomberg L.P., which he ran until 2014, when the now ex-mayor wanted his company back. The period that followed made Doctoroff’s six years in public office look even more fruitful. He took a job as CEO of the Google-affiliated smart-city start-up Sidewalk Labs, which hoped to develop a 12-acre slice of the Toronto waterfront. The site, called Quayside, adjoined a much more expansive stretch, dangling the promise that Sidewalk would start big, then go bigger.

The company’s plan for the new from-scratch neighborhood placed technology at the service of old-fashioned urban virtues. A network of plazas and pedestrian-first streets would be sprinkled with “lightweight, adjustable street furniture” — sort of like the peddlers’ carts and bicycle-powered knife-sharpening stations that are staples of improvised urban life across the developing world. Copenhagen-ish coziness would be upgraded with sensors and processors chewing through data and feeding it to a committee of artificially intelligent decision-makers. Messages would fly through the network, ordering sidewalks to melt snow, robots to deliver packages from central sorting facilities, streetlights to wait until a trudger has finished crossing, automatic vehicles to yield, electronic beacons to guide the blind.

Doctoroff overestimated his powers of persuasion. “At the beginning, he was regarded as a visionary guy from New York. Eventually, it became clear that he was so hell-bent on doing things his way that he wasn’t listening,” says Josh O’Kane, a Globe and Mail reporter who covered the project and wrote Sideways: The City Google Couldn’t Buy. “He made a lot of enemies with his working style. He likes to scream and yell, and we’re much more passive-aggressive in Canada. He really rubbed a lot of people the wrong way.”

It wasn’t just Doctoroff, who says he didn’t yell often. Sidewalk was staffed by veterans of some of New York’s most protracted and vitriolic real-estate battles, people who regarded negotiation between government and private developers as a contact sport with spittle and profanities flying on both sides. Marc Ricks, who was on Doctoroff’s staff-during the Bloomberg administration and later became a Sidewalk executive, recalls, “In New York, it was not uncommon for F-bombs to get tossed around in a meeting. In Toronto, we’d have a firm, modestly heated discussion, with no profanity, and you’d get a call afterward saying, ‘Whoa, your people were really aggressive.’ And I thought, You don’t know aggressive.”

In early 2020, Sidewalk killed the Toronto project; a year and a half later, Doctoroff received his ALS diagnosis and stepped down as CEO. It’s still not clear if, as some opponents claimed, the effort was doomed by a fundamental contradiction between the needs of a democratic society and those of a corporation intent on gathering proprietary data. Maybe it was just local developers and a homegrown tech industry closing ranks against an interloper. Possibly it was another instance of caricature being more effective than nuance. “Never have you seen a more significant disconnect between the way people saw themselves and the way others saw them,” Ricks says. “The technologists we attracted were the ones who were most geeked up about how you run cities, but to the outside world, we were big bad Google.”

One of my visits with Doctoroff at his home on Central Park West was a few days after Passover, the holiday when Jewish people rehearse their own history and don’t try to project any further into the future than the same time next year. His two Labradoodles, Sid and Ziggy, made an exuberant appearance, and Doctoroff told me they’re less interested in him since he can’t wrestle with them anymore. He has made a lot of small changes to his routine, sleeping with a ventilator, keeping a cough-assist machine at the ready, avoiding shoes with laces, holding a fork in his left hand. “You have to make adaptation into a fun challenge,” he says. “I’ve been really good about that.”

He has lived with the specter of the disease for a long time, but he says he doesn’t feel like fate singled him out. As he notes, ALS is not especially rare, and 90 percent of cases have no known genetic component. Doctoroff is the third member of his college class to be diagnosed — his roommate died in 2018 — and he’s pretty sure he won’t be the last. “I never believed I would get ALS, despite the genetic mutation in my family.” He refused to be tested, he says, because “if I knew I had it, I’d feel obligated to tell my kids, and I didn’t want to do that.” After his diagnosis, he learned that he doesn’t have the mutation. Had he been tested two decades ago, the result would have given him false reassurance. He kept the diagnosis to himself for a month and then called a family meeting. Tears were followed by gallows humor. “What’s been amazing to me is how emotionally intelligent my kids have been. They turned the dial up just perfectly in terms of responsiveness, affection, and presence without being overly emotional.” It’s hard to imagine such sustained clan harmony in the face of immense stress, but either Doctoroff has an extraordinary family or he wants to present it that way. He evidently draws strength from his children’s response — and takes some credit for it, too. “I do think to some extent they take their cues from me.”

His condition has been unexpectedly stable for almost a year, which allows him to continue sitting on the boards of three companies that spun off from Sidewalk, plus the Shed, Bloomberg Philanthropies, and the University of Chicago, as well as Target ALS. He schedules meetings on half-days: Mondays and Wednesdays from 8 a.m. to 1 p.m. and Tuesdays and Thursdays from 1 to 6 p.m. “I’ve been fortunate, and I can still learn, I can still make a contribution,” he says. “I’m probably busier than I want to be.”

At times, he can almost forget how temporary this reprieve is. “I’ve been almost completely independent, so it doesn’t always feel like it is what it is. It’s harder on my wife because she can’t help but think about what it’s going to be like to care for me or when I’m not around.” When I check in again a few months later, he’s spent the afternoon visiting the Roman aqueduct at Pont du Gard in Provence. He reels off the traveling he’s done since we last spoke: New Orleans, Knoxville, Florida, Puerto Rico, Detroit twice, Boston, and a bike trip with friends around Puglia. (He rode along on a Vespa.)

I begin to wonder if this family history might have been part of his drive to get things done in a hurry. Before I can even finish formulating the question, he’s deep into his pitch for Target ALS in power sales mode, the one he deployed for the Olympics, PlaNYC, Hudson Yards, and Quayside. “I’m optimistic — not that there will be a cure in my lifetime but that I’ll be able to choose between the best of not particularly great alternatives and live my life every day to the fullest.” For someone who claims not to be thinking about the future, Doctoroff sure spends a lot of time thinking about the future. “I’ve been debating what to do when I can’t really move,” he muses. “My wife and I are taking bridge lessons. Should I learn to play chess better? The eyes don’t go in ALS, so you can always look at a screen.”

New York, right now, is facing its own plight: Who needs Manhattan if everyone can work from home? Doctoroff expresses optimism on that front, too, partly because, to an astonishing extent, we’re all still living in his New York. Fifteen years after he walked out of government, the city is still working through his punch list and totting up its debt to him. Downtown Brooklyn’s first supertall was just completed. Affordable-housing towers are still going up at Hunters Point South. A new performing-arts venue, the Perelman Center, will open at the World Trade Center in the fall. Congestion pricing is finally on the way. Even Comptroller Brad Lander, who fought the subsidies for Hudson Yards back when he was a City Council member, recently acknowledged he’d been wrong: The development is sluicing tax revenue into the city’s reservoirs. Some fresh ideas, too, have Doctoroff’s fingerprints on them. The New New York panel recommends policies like the ones he wishes he had paid more attention to 20 years ago. It mentions child care 157 times.

And yet I wonder if he wishes he could do more — if, say, he had the time and wherewithal to stage another rescue. His brain trust is disappearing: Kriegel and Garvin, who trained him in the minutiae of New York politics and history, both died within the past few years. Two terms of the de Blasio administration failed to solve many of the problems it hoped to: Rents kept climbing, the homeless population grew, and big projects stalled. Now the rescue plan that Adams has ordered up reads like an old to-do list with more bus lanes, electric-vehicle charging stations, cargo e-bikes, better off-peak subway service — even “achieve clean streets.” They’ll all remain worthy bullet points unless they’re driven by an executive capable of single-mindedness about a thousand things at once. Adams just the other day announced his intention to carry out Initiative 12 from the New New York Plan: Reduce the number of sidewalk sheds. We’ll see. But is there anyone, I ask Doctoroff, who can deliver on the broad spectrum of magical thinking coming from City Hall? He answers with a highly diplomatic tautology. “There’s vision, but what really needs to happen is you have to execute.” I take him to mean that the Adams administration has appointed smart, clear-thinking people, including veterans of various Doctoroff enterprises. What’s missing is anyone with his maniacal focus, autonomy, and clout.

Photo-illustration (sources): Etienne Fossard/brooklynbridgepark.org, Courtesy of Highboro Concrete, Eloi_Omella/Getty Images, Diana Robinson Photograph/Getty Images, Noam Galai/Getty Images, Steven Ryan/Getty Images, Business Wire, Dansnguyen/Wikipedia, Dave Spencer/Splashnews

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