In this series

I’ve been writing about issues of poverty for four decades. My brief period of television presence came in the 1990s as the sower of “compassionate conservatism,” a plant that sprang up quickly only to have a thorn-choked death in the early 2000s. But for the past four years, the problem of homelessness has really bugged me.

One reason why is that while I’ve briefly interviewed homeless people since the 1980s, only recently have I spent extended time with individuals who have lived for many years on the streets.

My home on Edwards Mountain in Austin, Texas, has a 20-mile view to the west that encourages me not to think about homelessness, but I can close my eyes and picture 65-year-old “Cowboy.” I met him during my six-day stay in a Missouri village for the recently homeless where his tiny home was next to mine. He told me his wife, daughter, and two grandkids died when the Interstate 40 bridge over the Arkansas River collapsed in 2004. After that, he got drunk and stayed that way, he said, becoming “a missing person for nine or ten years.” 

I dug into old newspapers and saw that a 600-foot span of the Interstate 40 bridge over the Arkansas River did collapse on May 27, 2002, after a barge hit one of the bridge’s piers. But the Associated Press list of the dead did not include Cowboy’s family. A Christian staffer at the homeless village, saying Cowboy was melding reality and disappointment, suggested I not ask him about it anymore.

Another resident on my mind, Miranda, was in her 30s. (I’ll be using first names and nicknames throughout this series for the sake of its subjects’ future job prospects.) Miranda wore an ankle brace and spoke of her stays in foster care—the first, she said, came after her dad threw her older brother through the windshield. In 2017, she said, Miranda was walking along, six months pregnant, when a Dodge Ram 2500 hit her, injuring her and killing her unborn child. After that, she lived for the two years in the woods, using blankets a homeless outreach gave her to keep from freezing.

The 19th-century Scottish pastor Alexander Maclaren said, “The Christian life is not merely to unfold itself in peace and order, but through conflict.” Miranda has had plenty of conflict, but she is making progress despite a diagnosis of bipolar disorder.

The story is not so positive for homelessness generally. The world and the US have seen statistical improvement on many poverty issues, but homelessness has gone the other way. In 1970, the UN Food and Agriculture Organization estimated that one-third of those in developing countries lived in hunger. Now it’s one in 12 worldwide, and an estimated one in eight if we look only at poorer lands: still a tragedy, but less bad in a world with a history of sin and misery.

Domestically, while disaster headlines hit daily, we also have a partial success story. The Supplemental Poverty Measure suggests that from 1967 through 2018, US poverty dropped from 26 percent to 14 percent—less than 5 percent as measured by the Federal Reserve’s “full income” calculations. Many people don’t feel better off, but they are better off materially.

Homelessness statistics, however, have gotten worse. Before the surge of the past half century, Chicago’s “Skid Row” had a population of 12,000, but only about 110 of that number slept outside. As reported in The Men on Skid Row, Temple University medical students canvassing Philadelphia in 1960 found 2,000 homeless people in small rooms or barracks, and only 64 were on the streets. By 1965, the nationwide number had grown to 100,000 or so, according to Samuel Wallace, a University of Minnesota scholar who didn’t just study homelessness academically but lived with the unhoused to put faces to numbers. Others suggested 150,000 around the same time.

To come up with more accurate numbers, the Department of Housing and Urban Development (HUD) in 2007 began conducting “point-in-time” surveys each year, where on the same night researchers fan out in city after city to get an accurate count of the homeless. The 2025 count estimated that an average of 746,000 people were unhoused on any given night of the year. 

About two-thirds of them had some roof over their heads, often in unsafe government-funded warehouses. One-third were unsheltered, sleeping on sidewalks or among bushes. Programs and promises have come and gone during the 19 years since that first point-in-time count, but the number hasn’t diminished: Roughly a quarter million people are sleeping rough each night in America. 

Unless those people are living in the greenbelt behind your house, or on the sidewalk near your shop, or under the bridge near your place of work, or near the trail where you run, the homeless can become an abstraction. This makes it easy to look away. The problem may seem unsolvable—too big, too complicated, or maybe even too unpleasant.

Meeting people like Cowboy and Mary made it hard for me to think about “the homeless.” I now see particular human faces. I can no longer look away. And it’s left me with lots of questions that I’ll organize into four parts in this series: 

  1. Personal responsibility: Who are the people living on the edge? 
  2. Societal realities: What are the effects of demographic change and housing supply?
  3. Failures: What bright ideas have we tried, only to find they don’t work?
  4. Solutions: What are we (and Christians in particular) doing that works?

Because of the low-income-housing shortage that I’ll examine in my second section of columns, millions of Americans are at the edge of homelessness. My first question, though, is why some fall off the cliff. Please stick with me and I’ll show how the motto of one group that’s helping, #NoOneSleepsOutside, can become more than a hashtag. 

I’m learning about practical and proven ways to reverse the curses of the past generation in a manner that is humanely and financially sustainable. I want CT readers to learn about those too.

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