No one really knows how many homeless people there are in New York City, and no one ever has. The city’s official “daily census” tallies the population in the homeless-shelter system, but fails to count thousands of other New Yorkers living under borrowed roofs or open sky: people in domestic-violence shelters and temporary veterans’ housing, emergency shelters for people with HIV/AIDS, facilities operated by religious entities, shelters for runaway youth, or short-term beds attached to the correction system. It also omits the street homeless population, not to mention people who are housed only because they are briefly in a city jail, or found temporary refuge in a hospital, or are doubled up—for now, but probably not forever—with family and friends. All told, these categories could add up to 15,000 to 20,000 people.

Still, the official census is the go-to barometer of homelessness in the city, and it soared in the final years of Michael Bloomberg’s mayoralty. After Bill de Blasio’s stunning victory in 2013—a victory which he won, in part, by attacking Bloomberg’s failed record on inequality—The New York Times published a harrowing feature story on the journey of one girl, Dasani Coates, made through the city’s shelter system during the Bloomberg era. On Inauguration Day in 2014, Dasani held the Bible as the city’s new Public Advocate Letitia James took her oath of office, and the little girl looked on as de Blasio took his. Within two months of becoming mayor, de Blasio removed families from two of the notorious family shelters, including one where Dasani had been forced to dwell. “The transition at the Auburn and Catherine Street shelters is our first public step in a larger strategy to improve homeless services,” the mayor said in a statement, “while we address the underlying causes that have left a record-number of adults and children living in New York City shelters.”

Now, as de Blasio prepares his case for reelection, he presides over a shelter system that has set new records on his watch. As of Tuesday, May 2, there were 58,702 people in the system—over 8,000 more than the day Bloomberg left City Hall. Incomplete as it is, the shelter census is stark proof of the “tale of two cities” reality de Blasio condemned as a candidate and of the challenges the mayor has faced—some external, some of his own making—in trying to create a more inclusive New York.

There’s been no lack of activity on the mayor’s part. He has created new housing subsidies, spent generously on legal services to prevent evictions, taken steps to improve shelter security, and reorganized the homeless-services bureaucracy. Still, the numbers have climbed.

So the mayor hit the reset button in February, unveiling a plan that includes, among its central proposals, building up to 90 new shelters in the next five years while improving shelter operations and ending the city’s reliance on hotels and private apartments to shelter people. The plan also promises to whittle the numbers of homeless New Yorkers by 2,500—or a very modest 500 a year.

“This is a commitment to do something different….,” the mayor said when he announced the plan. “We will make progress, but it will be incremental. It will be slow, and I hope, and I believe it will be steady.”

Credit de Blasio with courage: Not every politician would open an election year with a vow to build seven dozen of the very facilities that have triggered ugly homeowner opposition in more than one city neighborhood.

Yet de Blasio’s plan manages to be dangerous without being daring. Building new shelters entails steep political risks for him. But it does not fundamentally change the course the city has traveled for nearly 40 years when it comes to people without homes: providing a crisis response to a permanent problem with a clear—though costly—solution.

As indictments of our economic system go, it’s hard to get more potent than homelessness. When people are sleeping under bridges, toting their life’s possessions around in a couple bags, begging on subway cars for cash to feed their kids—while others spend their days flipping real estate, either for profit or as hobby—something has clearly gone very, very wrong.

During the last 35 years, the evidence of something deeply amiss has mounted in New York City—and it has mounted despite near-constant lamentations over the breadth of the crisis and the efforts of five successive mayors to “do something” about it. What those mayors have done, more often than not, is apply the instinctive American response to poverty: blame it on personal failings and deny even the possibility of a systemic flaw. So, for much of the past few decades, city homelessness policy has been dominated by the notion that, if you made decent shelter too easy to get, people would leap out of the woodwork to fill up city beds. Homelessness, from this dominant viewpoint, was not a systemic problem—the result of rents that have soared too high, wages that have dropped too low, and a social safety net so tattered it fails to catch the most vulnerable—but a personal problem of which homelessness was merely a symptom. The issue has been behavior, not economics.

Ed Koch was the first mayor to deal with a large increase in homeless people—an increase that we have since come to recognize as the first wave of contemporary urban homelessness. While Koch is best remembered for an affordable housing plan that rejuvenated dozens of neighborhoods—and did set aside 10 percent of that new housing for homeless families—Koch was generally opposed to making it too easy for people to move from shelters to permanent housing. After all, the popular explanation for homelessness at the time was that state mental institutions had released too many people to the streets. (A better explanation for the crisis: the Reagan administration’s radical cuts to affordable housing coupled with rising rents, and falling incomes.)

David Dinkins initially rejected that approach and sought to make permanent housing easier to get—but when the 1990–91 recession flooded the shelter system, his administration was overwhelmed and he pulled back. Rudy Giuliani fully embraced the behaviorist approach, pursuing punitive policy against people in the shelters, including a bid late in his second term to force families to work for their shelter and throw homeless children into foster care if their parents didn’t comply.

Fortunately, the thinking about homelessness wasn’t confined to City Hall—and those academics and social-service professionals doing more thoughtful work didn’t see the homeless population as a monolith, a reality that underpinned a more sophisticated and humane set of policy ideas. They recognized that most homeless families—driven to the streets by forces like domestic violence, rising rents and stagnant wages—were different from most homeless individuals, who might be suffering from substance abuse or mental illness. In either case, according to  this new thinking, the proper response was not to punish people for their desperation but rather to get them the help they needed—namely, housing.

Progressive policy ideas emerged from this: “supportive housing,” which combines a stable place to live and treatment for individuals with mental-health or drug or alcohol issues; “housing first,” which focuses on getting those individuals a place to live before worrying about sobriety or treatment; and “rapid rehousing,” which aims to get homeless families out of shelters and into stable housing fast.

This thinking influenced Bloomberg’s approach to homelessness, although the billionaire mayor—owner of at least five homes at the time—was so clearly captured by the behaviorist view that it undermined his more enlightened policies. Bloomberg primarily saw homelessness as a management problem—one he promised to dramatically reduce—but he bought into the idea that perverse incentives were what made the status quo unmanageable. So, while Bloomberg did sensible things like increasing funding for homelessness prevention, he also fought to try to loosen the legal restraints that required the city to shelter people in need, and he cut off shelter residents’ priority access to public housing and federal-rent vouchers. Most frustrating, he created city-rent subsidies to get people out of shelters and into permanent housing, but so encumbered the program with time limits and other restrictions that some advocates cheered when a state funding cut killed it during Bloomberg’s third term.

Those choices, coupled with the devastating impact of the Great Recession and the displacement wave triggered by real-estate development that Bloomberg fostered at every turn, were big reasons why Bloomberg left office not having solved homelessness but instead bequeathing a much more severe crisis to his successor. The numbers of homeless New Yorkers initially bounced around under Bloomberg, from a nightly shelter census of just over 31,000 when he took office in 2002 to more than 36,000 in January 2004 and then back down by mid-2006. But it was up to 50,370 by the time he left office.

His successor, de Blasio, has certainly struggled to project command of homeless policy, beset as he has been by headlines about street encampments and deaths in the shelter system, ordering a major policy and personnel shakeup in late 2015 only to have to unveil the new one in February. But de Blasio has never embraced the behaviorist theory of homelessness that hampered Koch and Dinkins, defined Giuliani and underlay Bloomberg’s approach. He has consistently treated homelessness as a problem largely beyond the control of the families affected—one in which evictions and domestic violence are by far the biggest drivers of demand for shelter beds.

“Since the Great Recession, this has become a different and deeper problem because it’s more and more an economic problem,” de Blasio said in February. “Working people becoming homeless; families in record numbers ending up in shelter; people who don’t have any mental-health challenges or substance-abuse challenges, never been incarcerated, still ending up in shelter—that’s what we’re seeing more and more—that’s a more fundamental structural problem.”

The statistics speak for themselves. Over the 14 years before de Blasio took power, median rents in the city went up 19 percent while real incomes fell 6.3 percent. Republican-engineered deregulation sucked some 150,000 apartments out of the rent-stabilization system from 1994 to 2012. And half a million New Yorkers now shoulder rent burdens that are considered unsustainable. It ain’t rocket science. What the homeless need is housing.

A recurring irony of de Blasio’s mayoralty is that, while the mayor clearly outshines his predecessors on many scores—the extent of his policing reforms, the degree of his financial support for public housing, the strength of his efforts to welcome and protect immigrants—he is often seen as falling short, thanks to the scale of the problems facing the city and of the expectations built by his own grand rhetoric.

It’s arguable that de Blasio has done more to address homelessness than any other mayor who faced the problem—a feat that’s all the more impressive given the paltriness of support from the two major players that should be his partners: the federal and state governments.

In spite of that, de Blasio has provided record numbers of permanent housing units under an array of new programs to people leaving shelters (most are part of a policy umbrella called LINC or Living in Communities) and introduced a uniquely aggressive street-outreach initiative called HOME-STAT. De Blasio also ramped up public support for legal services to prevent evictions—a major cause of homelessness—among low-income tenants, and statistics indicate that evictions have dropped significantly.

The problem is that de Blasio didn’t want his mayoralty to be about homelessness, so the issue never garnered the full-court press that universal pre-K or his neighborhood rezonings have received. It also seems that, while de Blasio understood the nature of the problem better than other mayors, he has been caught off guard by its degree. As a result de Blasio has been reactive when it came to homelessness, making policy in fits and starts.

His new, 114-page plan in February is called “Turning the Tide on Homelessness in New York City”—its cover picture showed someone handing a set of keys to someone else—is meant to be the last start.

“Somehow, we’ve been moving in the wrong direction for three-and-a-half decades,” de Blasio told the crowd as he unveiled the plan. He noted that he had already put forward a set of initiatives to combat homelessness, but acknowledged, “we needed something bigger and stronger, and better, and that’s what this plan is meant to be.” He was not promising nirvana, the mayor said. “This is a blood and guts war strategy because we’ll be fighting this war for a long time. But I do believe we can do better. I do believe we can disrupt the status quo.”

It’s certainly a big deal to move away from the city’s use of private apartments and hotel rooms to house about 18,000 people at around 350 sites—although that process will take between five and six years under de Blasio’s plan. The move to start 90 new shelters, while also consolidate the existing shelter network, is a big haul too.

But for a plan triggered by the continued growth of the city’s shelter census, de Blasio’s program only aims to reduce the shelter population by 2,500 over five years—basically to where it was by mid-2015. It makes no provision at all for moving more people to permanent housing than de Blasio was already moving.

It remains unclear how many apartments created through the mayor’s 10-year, 200,000-unit, $41 billion housing plan will still be set aside for homeless families. The 176,000-apartment public-housing system, where thousands of units turnover each year, will still only offer 1,800 units to people coming out of shelters. The same goes for Section 8 vouchers. His LINC program of rent subsidies will continue at the same level.

It’s simply not enough. “At this critical juncture, the principal focus of City and State homeless policy must be on rapidly reducing the need for shelters by bringing permanent housing solutions for families and individuals to scale,” the Coalition for the Homeless said in an annual report released shortly after the mayor’s new plan. Other advocates concur. “The program they announced the other day is really merely a program to move people from scatter-site and hotel properties to shelters,” says Jeff Foreman, director of policy and advocacy at Care for the Homeless. “That’s what that program is about. It’s not a program to reduce homelessness.”

Accused often of being a visionary with lousy management skills, de Blasio seems intent on managing rather than really addressing a homelessness crisis that was bad when he arrived and grew worse under his watch. It’s certainly not the easy way out: Lawmakers are already clamoring to exempt their neighborhoods from de Blasio’s shelter-building plan, foreshadowing a nasty political fight ahead, while the price tag is unlikely to be less than the enormous $1.7 billion the city is spending this year.

The question is why he’s chosen this path.

De Blasio’s decision to fight for 90 new shelters rather than more permanent housing for the homeless connects to a foundational belief: that the city’s scarce housing resources have to be distributed across a range of needy groups. This is why his affordable-housing plan serves households making up to $138,435 for a family of four. The mayor’s people deny this effort to serve a broad range of income groups is motivated by politics. The mayor believes that housing need is so widespread in the city that government has a duty to extend a little help to as many sectors as it can. And he has argued that, for the poorest of the poor, the New York City Housing Authority  offers help that middle-class families cannot access.

Advocates, however, have pounded the mayor to shift more of the city’s housing resources from where they are helpful to where they are virtually the only hope. De Blasio has responded by adding low-income units to his housing plan. It’s unclear if, when it comes to homelessness, he is willing to be pushed. But de Blasio has shown remarkable flexibility in recent weeks, embracing the closure of the city’s sprawling jail complex, Rikers Island, mere weeks after dismissing the idea.

The 2017 campaign is now well underway. In most years it would create an opening to debate the thinking that guides de Blasio’s policies on the homeless. But so far no candidate has emerged to really challenge de Blasio. So he will have to figure it out on his own. When he says of his homeless plan, “This is a blood and guts war strategy, because we’ll be fighting this war for a long time,” he must ask himself, like any general, whether his target is worth all that carnage.