Mayor Wu Announces Award of $105,000 in Mini Grants to Reentry Organizations; Appoints Ashley Montgomery Executive Director for the Office of Returning Citizens

Mayor Michelle Wu announced the award of $105,000 in mini-grants to 21 Boston reentry organizations and the appointment of Ashley Montgomery as Executive Director for the Office of Returning Citizens (ORC). As Executive Director, Montgomery will lead the department's efforts to expand resources and services for returning citizens and assist the City of Boston in addressing the inequitable harms of incarceration. Montgomery will have the primary responsibility of driving the ORC’s vision and managing the day-to-day operations of an office charged with engaging, serving, and advocating for individuals returning to Boston from incarceration and impacted by CORI.

“We’re so grateful to have Ashley Montgomery stepping into leading the Office of Returning Citizens,” said Mayor Michelle Wu. “Her experience in supporting individuals with substance use disorder and her work to reduce recidivism proves her ability to advocate and improve the lives of people reentering society.”

The mission of the Office of Returning Citizens is to help returning citizens recover from the trauma of incarceration, reclaim their dignity and purpose, and rebuild their lives through positive choices, incentives, and opportunities. The ORC aims to empower its clients to break the cycle of recidivism through hands-on case management and an extensive provider referral network. Montgomery's dedication to public service and her impactful leadership has facilitated positive change in the lives of those reintegrating into society. The ORC is housed within the Mayor’s Office of Human Services, led by Chief José F. Massó. 

“We are excited to bring Ashley Montgomery on board as a seasoned leader for this Office,” said José F. Massó, Chief of Human Services. “Ashley’s deep experience in service delivery and her commitment to our City’s formerly incarcerated residents will be a significant benefit to the Office.”

"I am honored to accept the position of Executive Director for returning citizens. With compassion, dedication, and a commitment to restoring dignity and opportunities, I look forward to leading initiatives that empower individuals to thrive beyond their past challenges." said Ashley Montgomery. "As I step into this role, my commitment is to foster a collaborative environment where community partners unite to support formerly incarcerated individuals. By breaking down silos and pooling our resources, we can empower individuals on their journey to successful reintegration into society."

The ORC helps over 3,000 people who return to Boston each year from federal, state, and county prisons and jails take healthy steps in their lives through a variety of services. These services include in-person case management with program and intake coordinators, peer mentorships, and warm referrals to key programs and services, including transitional housing, employment, healthcare, education, and legal services. Between the Office’s inception in 2017 and today, the number of yearly clients served by the Office has increased by more than 700%. 

For Fiscal Year 2025, the Office of Returning Citizens has a $2.3 million operating budget. The Office has grown from two to seven staff in the past two fiscal years, and is in the process of hiring for four open positions. Since FY23, the Office has granted out over $2 million in city funds to community-based partners that serve individuals who are returning home to Boston from incarceration. This latest round of funding will support 21 non profit organizations in Boston that offer various supports and services to returning citizens, including housing, entrepreneurship education, clothing, family reunification and legal advocacy. The grants range in size from $3,500-$7,000. 

Prior to this appointment, Montgomery served as the Chief of Staff and Interim Executive Director of the Office of Returning Citizens. Before joining the administration, Ms. Montgomery worked for the Commonwealth of Massachusetts for thirteen years. Most recently, she was the Director of Regional Operations at the Bureau of Substance Addiction Services, showcasing her commitment to addressing complex societal challenges. Montgomery also worked as the Director of Data Analysis and Quality Management at the Massachusetts Department of Mental Health for eight years, where her work centered on program quality improvement, and as a Criminal Justice Research Analyst, where her focus was understanding barriers that lead to recidivism.