Leon Winston, an Advocate Committed to Ending Veteran Homelessness

written by naehblog
November 14, 2013

Like many people who work in the homeless assistance field, Leon Winston had his own personal experience with homelessness and hardship. He was homeless himself, more than once, and a veteran. Now he is chief operating officer and housing director at Swords to Plowshares, a nonprofit that serves homeless veterans in the San Francisco area. Today, as part of our Never Another Homeless Veteran Campaign, we’re sharing his remarkable story of how he got there, in his own words.

His story is unusual, but we believe it’s emblematic of the commitment we need from the public and our elected officials if we are to end veteran homelessness. That’s why the Alliance awarded him our Veterans Champion Award. And it was his kind of commitment we had in mind when we drafted the Never Another Homeless Veteran statement.

We commit to ensure the continued dignity of the men and women who have shown courage and resolve in the defense of our families, friends, and freedoms.

If you agree, please join the Alliance, The Home Depot Foundation, and the thousands of others around the country who have already signed the Never Another Homeless Veteran statement.

Yes, I'll sign the Never Another Homeless Veteran statement.

Here is Leon’s story.


I was homeless for a second time when, in 1993, I was referred to Swords to Plowshares’ transitional housing program upon discharge from inpatient treatment at the San Francisco VA Medical Center. I had been “down the rabbit hole” for about five years before my admission to the hospital, a period that was bookended by stretches of homelessness in Los Angeles and San Francisco. Self-medication for lifelong bouts of depression had turned into several years of methamphetamine addiction. It was far from pretty, and to this day often wonder how I managed to come out the other side.

Prior to that period I had worked in the financial services field for 13 years, something that I never liked but which I fell into for need of a job following my discharge from the Navy amid the recession of 1974. But to escape homelessness, to that field I returned before graduating from Swords’ program in early 1995. It afforded me an income sufficient to find a place to live – but I truly disliked it.

Within a few months’ time I contacted Maceo May, Swords’ Housing Director, and asked him if there was any possibility of my going to work for the agency. I came to understand that finding meaningful work was much more important than the paycheck itself, particularly so if I was to continue on my path of recovery. I had lost everything twice, prior to coming to this place in my life. One thing that losing everything allows someone is the freedom to reinvent oneself, and I needed reinventing. That included securing meaningful work.

A few weeks later, Maceo called me and asked if I would like to come in and interview for a Program Assistant position with the transitional housing program. It paid about half of what I was then earning, but I gladly began working for Swords in that capacity during August of 1995. Like many in early recovery looking for a new role in life, I thought that I wanted to become a counselor, and enrolled in Alcohol & Substance Abuse Studies curricula at U.C. Berkeley, concurrently with undergraduate courses in psychology elsewhere.

In time, I realized that I might not be well suited for the helping professions but that my business background could actually be of benefit to the nonprofit sector as I was experiencing it on a daily basis; I could do ‘good work’ supporting those that were working directly with clients. I realized that I might not be well suited for the helping professions but that my business background could actually be of benefit to the nonprofit sector as I was experiencing it on a daily basis; I could do ‘good work’ supporting those that were working directly with clients.

I set about to be as impactful as I could with this new found direction and, built upon the foundation of understanding the substance abuse and mental health nature of the work, designed a course of study towards that end. In so doing completing a BA in Public Administration followed by a Masters in Nonprofit Administration and Organizational Development, all while working up the ladder of progressive responsibility at Swords to Plowshares.

During the last 18 years, effectively addressing homelessness – veteran homelessness in particular - has become my life’s work.