Teacher inspired to educate prisoners to give them — and their communities — a shot at a better future

“He shared with the class that it was the greatest accomplishment of his life.”
Pictured left to right: Gayle, Woody, Judy, and Oprah

Pictured left to right: Gayle, Woody, Judy, and Oprah

Over the years, Judy Square has been blessed to spend time teaching in the Santa Rita Jail in Dublin, Alameda County, CA. Some of her most inspiring conversations have occurred in those rooms. In her conversations with incarcerated individuals, a common thread is that access to adult education offers them a chance to process their past and envision a new future. 

“Many students have told me that no one ever believed in them before, or thought they were smart,” says the San Leandro resident.  But working with Five Keys, they feel someone finally believes in them and is rooting for them.”

During the last 17 years she has taught at the now-closed North County Jail in Oakland and Santa Rita jail, one of the largest jails in the United States. Square says her favorite students to teach are inmates. For 13 years she worked at the jail through the Tri-Valley Regional Occupational Program and the last four through Five Keys.

“I've had a few students who have worked 8-10 hours a day on their schoolwork in their cramped cells, no desk, with stubs of pencils, sometimes with no erasers, pushing through all the obstacles and discomforts to earn their diploma,” she says.  

Of the about 200 students she has taught through Five Keys, one student, Nathan, especially stands out. 

“When I informed him that he earned his High School Equivalency Diploma, he jumped out of his seat and pounded the wall in celebration,” she says. “A deputy rushed in to see what was happening and I had to explain that everything was OK, and that Nathan was simply happy. Then the deputy left, and Nathan shed some tears in full view of his classmates even though that is usually avoided at all costs in jail culture. He shared with the class that it was the greatest accomplishment of his life.” 

For Square, teaching through Five Keys seems to be a natural extension of the ministry she shares with her husband Woody, who is pastor  and children, youth, and family minister at San Leandro Church of Christ.  The couple, who are parents of two young adults, spent six years in Papua New Guinea helping run a church leader training school.

When the pandemic hit the nation in March, Square and her teacher peers and principal were forced to rethink how they would provide service. The team quickly pivoted to salvage education for their students. 

Before the summer break, Square and other teachers typed letters every week, personalizing them for each student and sending them packets of educational materials to work on. An Inmate Services Deputy acted as a courier. He would deliver the letters and packets and bring back completed ones for Square and her fellow teachers to grade and record on the student's record. They also included feedback forms with their letters so the students could write back with questions or updates. 

“However, once things shut down, many students fell off the wagon and stopped completing schoolwork,” she says. “Because all of our students are high school dropouts and have struggled with their educational journey in the past, they really need the structure of classes and face-to-face interaction with teachers to keep them progressing.”

Teaching in COVID-19 has taught Square and other teachers how important the Five Keys mission is and vital to the future of inmates. 

Armed with a “yes-we-can-do-this,” they are planning to be back better than ever in August.  They will continue to deliver the packets of educational materials and keep the education going. 

“I can't wait until I can go back and work with my students in person,” says Square.

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A Walk in the Woods with Oprah

It’s not every day that campers at the Yosemite National Park run into talk show queen Oprah Winfrey on the trail.

But that’s what happened to Five Keys teacher, Judy Square, and her husband Woody, a minister, about 10 years ago, when they were on a visit to Yosemite.

The seasoned campers bumped into Oprah and her best friend Gayle King when the duo had hitched a pop-up camper to a Chevrolet Tahoe hybrid and hit the road to do a story about Shelton Johnson, a black park ranger who complained that few African-Americans were campers.

Not so, Oprah discovered. Oprah and Gayle ran into the Squares at their first stop in Yosemite and thought it would be fun to fly them out two weeks later to be in the audience when Oprah taped the Yosemite episode. At the end of the show, Oprah called them up on stage and surprised them with the keys to both her camper and the SUV that was used to pull it! Both vehicles were shipped from Chicago to San Leandro, and Judy and Woody still use the camper about three times a year and enjoy riding around town in their "Oprahmobile."