Robert Tomaszewski attained a Bachelor of Arts degree in Criminal Justice from Temple University in 1991.  He attended Saint Joseph's University and graduated with a Master of Science degree in Criminal Justice in December 2003.  At Saint Joseph's University, his concentration has been on Corrections, Victimology, and Restorative Justice.

Robert Tomaszewski began his career at the Philadelphia Prison System in 1984.  Serving at House of Correction, Holmesburg Prison, Philadelphia Industrial Correctional Center, Detention Center, and as Admissions and Diagnostics Manager for the Classification, Movement and Registration Division, Mr. Tomaszewski was promoted through the ranks, finally being promoted to the rank of Deputy Commissioner in April 2005.