Skip to main content

Second Chance Month Spotlight

Reynolds Allen Wintersmith
Reynolds Wintersmith

In honor of Second Chance Month, the Office of the Pardon Attorney would like to shine a light on clemency recipient Reynolds Allen Wintersmith, Jr. Mr. Wintersmith is a youth advocate and mentor and a partner in his community, who was granted commutation of a life sentence by President Obama on December 19, 2013. 

Reynolds Wintersmith, Jr. was 16 years old when his then-caretaker, his grandmother, was sentenced to prison and turned guardianship over to the founders of the cocaine and crack distribution conspiracy in which he would later be convicted of participating. He was tried at the age of 19 and was just 20 years old when he was convicted and sentenced to a term of life imprisonment under the then-mandatory Sentencing Guidelines; he had no prior convictions.

While incarcerated and with no promise of ever being released, Reynolds concentrated on making positive strides, achieving goals that included receipt of his GED and then completion of a 4,100-hour teacher’s aide program sponsored by the Department of Labor, which he then used to teach literacy and GED classes to other inmates. Additionally, he completed multiple vocational programs and successfully took on a host of educational coursework.

With clemency being his only apparent path of recourse, Reynolds’s counsel worked to spread awareness about his case, highlighting his youth, lack of criminal record, and the nonviolent nature of the offense. His story garnered a great deal of public support. After serving over 20 years in prison, he was granted commutation of his life sentence of imprisonment.

Reynolds has gone on to earn an associate’s degree in Child Psychology/Juvenile Criminal Justice and Sociology. He is a licensed professional educator and also maintains a special education program instructional license. He began working as a counselor at a Chicago alternative academy soon after his release, where he worked for eight years and was praised for reaching students in a manner that transcended classroom walls. He now operates a consulting company in Rockford, Illinois, through which he continues his outreach to young people in his community. He has also furthered his work with both youth and adults with special learning needs, working closely with Stepping Stones of Rockford, a nonprofit organization that provides residential mental health services. Reynolds has spoken openly about the experiences that shaped both his childhood and adulthood in various forums, including on Capitol Hill. 

Updated April 2, 2024