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Charitable Giving

My surprising education in starting a charity

When a Globe Magazine reporter wrote about Boston boys using basketball to try to beat the odds, he was moved to act.

Keyana Washington was the first Alray Scholar to earn her degree.Vincent Auyeung/Vincent C Auyeung
Alray Taylor. File

TEN YEARS AGO, I introduced Globe Magazine readers to Ridley and Hood and the other boys from Roxbury, Dorchester, and Mattapan who traveled across Boston every day to attend Charlestown High School and play basketball for coach Jack O’Brien.

By the time the articles appeared in the magazine in 2005, I had already spent nearly an entire school year immersed in the lives of these young men. I had seen them bask in the triumph of a state championship and withstand the sting of setbacks and even tragedy. Along the way, I came to care deeply about what happened to them, even if I knew I had to resist any urge to intervene in their lives.


I was so taken by the story that I stuck with it for several years more, eventually turning it into a book called The Assist. I saw up-close just how narrow the margins are for young men growing up in urban America.

Journalists often boast that we get a front-row seat on life, and that’s true. But in important ways, we are restricted from straying beyond the sidelines.

When I sat in the back of a courtroom and witnessed Hood’s college scholarship and promising future being snuffed out over an incident involving little more than a busted windshield, I wanted to stand up and scream at the judge. Knowing how precarious the path out of the projects could be, I worried his overreaction to Hood’s poor judgment would set off a disastrous cascade. But the most I could do to convey outrage was to underline observations in my notebook.

It was only when the book was about to be published in 2008 that I realized I could finally do more, if not for the guys I was writing about, then at least for others like them. I decided to donate some proceeds to a Boston nonprofit. That’s where my own education began.


IN ADDITION TO BUILDING the winningest basketball program in the state, Jack O’Brien had steered more of his players to college than any other coach in the city. Yet I learned how easily Boston students could get off-track, leaving college before earning their degree.

I decided I would support an organization working specifically to help Boston students return to college. Slight problem: Although there were good programs helping launch Boston students into college, I couldn’t find a single one focused on the reality of reentry. The psychological, financial, and logistical burdens for these returning students could be overwhelming, yet somehow they were expected to shoulder them alone.

One afternoon, as O’Brien and I walked around the outdoor track at Charlestown High, I told him about my inability to find an appropriate nonprofit. Rounding the bend, he stopped. “What if you started one?” he asked, adding, “You know, in memory of Alray.”

Alray Taylor had been a star of three straight championship Charlestown squads. I had gotten to know him years after that run, as we sat in the stands watching O’Brien’s younger guys play. Alray had grown up on the streets of Mission Hill, the oldest of seven. He was 6-foot-3 and 220 pounds — so big and fierce under the boards that people called him “Horse.” Off the court, he was so gentle and friendly that the cafeteria ladies loved to slide him extra desserts.


He had given up a Division I college scholarship to transfer to a smaller school, and then left college altogether to help his siblings after both his parents died in the span of less than a year.

No moment in my book research was more wrenching than the September night in 2006 when I joined hundreds of mourners in the New Hope Baptist Church — including the Townie lunch ladies, now sitting together in a pew, dabbing their eyes with tissues.

Alray’s murder was a billboard for the senselessness of urban violence. A bighearted young guy walks into a Hyde Park convenience store in broad daylight and somehow gets into a scuffle with a thug. The scuffle turns into a fistfight that Alray is easily winning, until the thug pulls out a gun and shoots him dead.

I was immediately sold on the idea of creating something lasting in memory of Alray, who had been in the process of returning to college. But I have to admit that, at the time, I also thought this: How hard can it be to set up a small nonprofit?

There are nearly 1 million 501(c)(3) public charities in this country, with 42,000 new ones approved in just the first nine months of 2015. I wonder how big a role naivete plays in getting people off the sidelines, and in keeping those numbers high.

I worked with friends to found the Alray Taylor Second Chance Scholarship Fund, incorporating in 2009 and later rebranding it as the Alray Scholars Program ( If I had realized then how much time it would consume and how often I would feel in over my head, I doubt I would have gone forward with it. I’m grateful I was ignorant.


The Alray Scholars Program helps Boston students, like Rachel Regis (pictured with Neil Swidey), return to college.SARA DROWER

I grew up in a family that didn’t spend much time on the sidelines. My parents were both public educators who regularly opened our home to their neediest students. Getting involved is more complicated, though, when you’re a journalist because of the professional obligation to keep your distance. Still, I figured out how to walk this line.

For starters, the Alray Scholars mission — helping low-income students return to college and earn their degree — is not controversial. There’s no worse a college-debt bind than being saddled with lots of loans that have to be repaid but lacking a degree that would dramatically boost earning power.

I’ve had to steer clear of soliciting funds and grants, to avoid potential conflicts of interest in my reporter life. So early on, we relied on the initial seed money and support from friends and family. As the Alray organization matured, others on our team have overseen the work of securing grants, notably one that allowed this all-volunteer nonprofit to hire its first part-time director.

It wasn’t long before we realized we would need to provide more than just financial support for our scholars — most of them first-generation college students with no safety net. We decided to pair each scholar with a dedicated mentor and make Alray about mentoring as much as anything else.


BACK IN 2008, people were only faintly aware that two out of every three graduates of Boston Public Schools who started college failed to earn any type of degree. Awareness is higher today, and the numbers are moving in the right direction. But Boston’s college completion rate remains low — distressingly low for black and Latino students from poorer families.

The Alray Scholars Program is too small to reverse those numbers on its own. But the organization is making a real difference in the lives of our scholars. In just a few years, we’ve admitted more than 50 students. Already 13 have earned their degrees, and many more are poised to do the same. This year brought our biggest applicant pool yet, and a new group will be admitted later this month.

Despite the growth, we’ve forged what continues to feel like a big extended family. After friends made memorial donations to Alray following my father’s death last year, the board created a Finish Line Fund award in his name. It gives scholars an additional infusion of financial support in their final year, to help them clear the last hurdle.

The first two recipients of that award illustrate what makes me most hopeful about the future of this organization. Liz Cabrera got her bachelor’s degree from Northeastern with assistance from Alray, and then kept going to earn her master’s. Now a social worker, she serves as co-chair of the Alray applications committee, helping to select our new scholars. Rachel Regis started with Alray in 2009. She returned to Johnson & Wales and completed all her academic requirements for her bachelor’s, but a loan morass kept her degree out of reach for several years. She stuck with it, though, and Alray stuck with her.

Today, she has that framed degree and a good job. On top of that, she’s an Alray mentor, sharing her wisdom with one of our newest scholars.

I still cherish my front-row seat as a journalist. But sometimes there’s nothing like getting in the game.

Neil Swidey is a staff writer for the Globe Magazine. E-mail him at and follow him on Twitter @neilswidey.