Board of Directors

Maria Hayley

Founder & Board of Directors - President

Ms. Hayley, who holds a Master of Arts in Library Science from Dominican University (formerly Rosary College), has more than 30 years’ experience in the library field. She specialized in correctional librarianship, young adult services, children’s services, programming, product development, outreach and administration. She has a record of innovations in these areas of endeavor. Her work has had neighborhood, citywide and national exposure. Additionally, through her studies at the Erikson Institute, the National Teachers Academy and independent studies with Clinical Professor of Pediatrics Emeritus at Harvard Medical School, T. Berry Brazelton, M.D., she has added expertise in early childhood development. Ms. Hayley’s background is context for continued search for cutting edge information impacting the mission of The Freadom® Road Foundation which is to break the cycle of intergenerational incarceration.

During her ten years’ experience as administrative librarian at the Cook County Department of Corrections (Cook County Jail) in Chicago, Illinois, Maria Hayley realized that many of the children born to incarcerated parents would likely follow in their parents’ footsteps. She decided to dedicate her life to discover ways to prevent and alter these probable futures. The continued search for root causes and solutions to intergenerational incarceration is the work of The Freadom® Road Foundation which she founded.

Ms. Hayley has been an accreditation consultant to The Chicago Metropolitan Correctional Center Education Department for 20 years and served on various boards including: The Cook County Department of Corrections Literacy Board (which she founded), the Local School Council of The Cook County Jail High School, The (Chicago) North Avenue Business Association, The Kiwanis Club of Lake View Foundation for Physically and Mentally Challenged Children ,The Family Focus-Englewood-Lawndale Advisory Board and The Board of the Jessie “Ma” Houston Prison Outpost of Rainbow Push Coalition.

Ms. Hayley’s awards include: Librarian of the Year (Chicago Pubic Library), Malcolm X Chicago City College Award, Spirit of Sulzer Regional Library Award, Chicago Torch of Service Award (The Chicago Library Heritage Society), A Gateway Foundation Award and awards from organizations, agencies and businesses in various Chicago Neighborhoods she has served. Before retiring from the library profession she was awarded a Proclamation from the City Council.

Maurice Littlefield

Board of Directors - Treasurer

Maurice Littlefield has a history of leadership in higher education, student relationships and financial development.

Originally from the east coast, Mr. Littlefield has since lived in Lexington ,Virginia.

He has served in the following positions: Educational Leadership Consultant, Sigma Nu Fraternity; Assistant Dean of Students, University of Maine; Dean of Students, University of Southern Maine; Assistant Director of Alumni Relations, University of Maine; Associate Director of Development, University of Maine; Director of Development, Old Dominion University and Executive Vice President, Sigma Nu Educational Foundation.

Since his retirement from academia Mr. Littlefield has been active in civic, faith, community and not-for-profit organizations in Lexington, Virginia and Chicago, Illinois.

Queen Mother - Rev. Helen Sinclair

Board of Directors - Vice President

“Queen Mother” Rev. Helen Sinclair is a living legend. Born on July 14, 1920, she has followed in the footsteps of her famous mother Jessie “Ma” Houston. Like “Ma” she has dedicated her life to prison reform, correctional ministry and civil rights. Reverend Sinclair is National Director of Jessie “Ma” Houston Prison Outpost of Rainbow Push Coalition. The original Prison Outpost was founded by “Ma” in whose honor a Chicago Park was named.

An ordained worldwide prison minister, Reverend Sinclair was named the first and only female chaplain in adult male maximum security prisons in the Illinois Department of Corrections. She logs thousands of miles yearly visiting these prisoners. She listens to them, prays for them, counsels them and advocates for them. She has recruited others including Mayor Harold Washington, Minister Louis Farrakhan, Reverend Al Sharpton, Congressman Danny Davis, County Commissioner Bobbie Steele and Du Sable Museum of African American History Founder, Dr. Margaret Burroughs to minister to the prisoners with her.

In her international work she has serviced in Israel, the Peace Corps in Central Africa and Cuba.
She has marched with Dr. Martin Luther King, Jr., Dick Gregory, Al Raby, Reverend Jesse Jackson and many other Civil Rights Movement legends.

She holds a BA in Public Administration/Criminal Justice from Northeastern Illinois University and a Certificate in Early Childhood Development from Harry Truman Chicago City College which she earned at age 65!

She has won awards covering three walls of her home. Among these awards are several from three Illinois Governors!

Anna Crockett

Board of Directors - Secretary

Anna Crockett is the Founder of Executive Function Matters – a coaching, tutoring and consulting entity based on cutting edge research findings in the neuroscience and cognitive sciences related to learning and the brain. It transforms students who find themselves overwhelmed and doubting their ability to succeed.

Prior to founding Executive Matters, Ms. Crockett was Director of the Miller Academic Center, Director of Learning Programs and Associate Director of Disabilities Services at the Virginia Military Institute.

She has attracted invitations from The University of Richmond as External Program Reviewer, from Washington and Lee University as faculty trainer, The International Mentoring Association as Conference Presenter and the College Reading and Learning Association (CRLA) as Conference Evaluation Chair.

She has served in leadership capacities in many local, regional, national and international organizations including the College Reading and Learning Association (CRLA) and the International Mentoring Association where she has held numerous positions including Chair, Treasurer and Region Director.

Ms. Crockett’s publications include “Executive Functions and Self-Regulated Learning” in the Handbook for Training Peer Tutors and Mentors edited by K. Agee and R. Hodges (2012). She has recently designed “Executive Functions/Academic Coaching: The G.R.I.T. Model (Goals, Responsibility, Initiative, Tenacity) Flow Chart. Some of her other works are cited as references in the prestigious Cengage Learning Textbook.

Dr. Rita Simo

Board of Directors

Dr. Rita Simo, Founder of the only free music school of its kind in the United States -The People’s Music School in Chicago’s Uptown Neighborhood – was born in the Dominican Republic. Dr. Simo’s drive to build such a school in the United States stems from her conviction that – as is the case in the Dominican Republic – a quality classical music education should be available to all children regardless of ability to pay. Her dedication to this cause is evident in the multi-million dollar music school she grew from only a dream, $626, a one room storefront, and a piano donated by St. Thomas of Canterbury Catholic Church.

As former National Concert Pianist of the Dominican Republic and graduate of the Julliard School of Music in New York and of Boston University, she has taught master classes, played solo concerts, performed with numerous chamber music groups and soloed with orchestras on three continents.

Just a few of Dr. Simo’s numerous awards include Exito Newspaper’s 1997 Personage of the Year, Chicago Magazine’s “The New Centurion’s” 2001 Chicagoan of the Year, Mont Blanc de la Culture’s 2005 Patron of the Arts for North America and 2013 Chicago Aguijon Theater’s International Women’s Day Award.

Dr. Simo’s story is told in the book Music is a Gift: Pass It On: Rita Simo and The People’s Music School by Cynthia Willis Pinkerton.