Kenneth is extensively involved in pro bono work. He serves as pro bono counsel, director and a volunteer for UMOJA Student Development Corporation. UMOJA links the educational efforts of many at-risk, under-resourced Chicago Public High School students to the broader community and serves as an advocate for young people, through academic, college preparation, leadership and life skills programming and support. In 2007, the Chicago Bar Association cited Kenneth's extraordinary pro bono service for UMOJA when it honored DLA Piper with the Abraham Lincoln Marovitz Lend-a-Hand program's Law Firm Partner of the Year Award. In 2013, he received the Pro Bono Champion award from Chicago Appleseed Fund for Justice.
Kenneth has co-authored three amicus curiae briefs with the United States Supreme Court on behalf of the American Bar Association on matters involving juvenile sentencing and juvenile justice issues. He co-authored the brief in the case of Miller v. Alabama (10-9646) and Jackson v. Hobbs (10-9647), in which the ABA—considering the unique vulnerabilities of children making them more impulsive, more vulnerable to peer pressure, less able to consider the long-term consequences of their actions, and with greater capacity for rehabilitation than adults—urged a ruling declaring unconstitutional the practice of sentencing children convicted of homicide offenses to life in prison without the possibility of parole.
Kenneth authored the amicus curiae brief on behalf of the American Bar Association submitted to the United States Supreme Court on December 23, 2010 in the case of J.D.B. v. State of North Carolina (No. 09-11121) urging the Court to consider the unique vulnerabilities of children subjected to police questioning for purposes of determining when a child facing police interrogation should have the right to counsel or the presence of a parent or guardian. In July 2011, the Washington Post quoted him commenting on the decision in that case, in "Supreme Court ruling, rising police presence in schools spur Miranda questions."
He also co-authored the amicus curiae brief submitted to the United States Supreme Court on behalf of the American Bar Association in Graham v. Florida, 130 S. Ct. 2011 (2010), in which the Supreme Court declared unconstitutional the sentencing of juveniles to life in prison without the possibility of parole.
Kenneth also served as a leader of DLA Piper's large-scale, long-term, innovative signature Juvenile Justice Project. As part of this effort, he served as the senior editor of From Juvenile Court to the Classroom: The Need for Effective Child Advocacy, a substantial policy study assessing and facilitating the reform of the process by which children transition from the juvenile court system back to school. The project was honored by the Illinois State Bar Association in 2005 and again in 2007 with the John C. McAndrews Pro Bono Service Award. In 2008, the success of this project also contributed strongly to the ABA's decision to award DLA Piper its Pro Bono Publico Award.
Kenneth has also represented several individuals in pro bono matters. He was named DLA Piper's Pro Bono Partner of the Year for the Chicago Office in 2004, 2006 and 2010.
Kenneth also serves as director of the National Juvenile Defender Center based in Washington D.C.