When he was in prison, Harold Bailey said, he would often think about the homicide that resulted in his 20-year incarceration and about how his criminal record might cost him opportunities for employment or education.

To continue the undergraduate education he had worked at for two years, Bailey would sit in his cell and voraciously read novels, autobiographies, academic texts — any work he could get his hands on.

Since his release in 2005, Bailey has earned two degrees, a bachelor's and a master's, from Coppin State University. Under a $60,000 grant to be announced Monday by the Open Society Institute of Baltimore, he plans to teach other formerly incarcerated black men reading, writing and re-entry techniques.

Bailey, whose program is called Re-entry Employment and Economic Empowerment, was one of 10 people to receive the OSI's annual grant for their work helping the underprivileged in Baltimore.

Pamela King, the organization's director of community fellowships and initiatives, said the grantees have often worked intimately with the communities they intend to aid, which affords them an inside view of the problems. Or, like Bailey, they have gained understanding by living in a marginalized community.

Policymakers may not have a complete understanding of the issues that affect these individuals, King said.

"Folks think they're addressing a problem," King said. "But it may not be addressed effectively. These individuals really understand the nuances of what's missing because they have some degree of independence and creative control."

When prisoners are released, Bailey said, they often return to the community where they committed the crime, which only increases the likelihood they will commit another.

"These people are helpless and hopeless," he said. "And toxic personalities will tell them they have dreams they can never hope to achieve."

While the program will be housed at Bailey's church, Heritage United Church of Christ, he will travel weekly to all three city locations of the Tuerk House, a substance abuse treatment and recovery center.

His curriculum will teach what he describes as life skills: developing a resume and professional portfolio. He will also work to adjust the former prisoners' attitudes.

"A little consideration goes a long way," he said. "I've told those I've worked with that 'please' should be the first thing out of your mouth and 'thank you' the last. I'll also incorporate nontraditional items like financial literacy, politics, whatever they need to be a well-rounded person that people like working with."

Eventually, he said, he would like to see some of the graduates of his program become instructors themselves.

"I want to achieve success and inspire and motivate these men to make a positive impact in their community," he said. "Maybe we can affect one to two, which in turn can affect three to four, and have a geometric impact. I am quite ambitious, and I hope to make this a national model."

King said several programs have grown significantly since their start. This past year, the OSI was also able to develop an alumni fund, granting up to $25,000 to initiatives that are already active.

One went to Hand in Hand Baltimore, a nonprofit that works in correctional facilities and in the surrounding communities to rehabilitate youth charged as adults in Maryland.

Since 2009, the program has served 140 young men — 90 inside the detention center and 50 in the community. Of those 50, 85 percent have not committed new offenses, 50 percent are employed and 90 percent have remained in their educational programs.

"There's an idea that you can only work at a certain place or if you're in detention you can only do certain careers, that you can only be a janitor," Jessica Turral, director of Hand in Hand Baltimore, said. "We introduce new career paths, encourage them to go to college."

Other grant winners this year include Akil Rahim, who wants to introduce parents of children living in poverty to science, art and mathematics programs for use at home; Anne Kotleba, a MICA graduate who wants to teach others to document social justice issues with various media; and Bashi Rose, whose program, D.R.A.M.A. (Direct Responses Alleviate Misdirected Aggression), will work within five Maryland prisons to teach incarcerated black men how to use theater and film to express their emotions in lieu of violence.

An earlier version of this article misstated the monetary amount of the grant awarded to Harold Bailey. The Sun regrets the error.