Rolley attended Rutgers College and was admitted into the school’s Honors Program. At Rutgers, he was a James Dickson Carr Scholar and a recipient of the Buttonwood Scholarship. In his junior year at Rutgers College, Rolley was accepted into the Eagleton Institute of Politics as an Undergraduate Associate. In 1995 Rolley was also accepted into the Woodrow Wilson Fellowship Program, and after the successful completion of Princeton University’s Woodrow Wilson School of Public and International Affairs Summer Institute, he was granted the prestigious Woodrow Wilson Fellowship. In 1996, Rolley graduated with honors from Rutgers College with a B.A. in Political Science and Africana Studies and went on to attend the Massachusetts Institute of Technology for graduate studies in City Planning with a concentration in housing and community economic development. While in graduate school, he worked as an Urban Development Technician for the Jersey City Department of Housing, Economic Development and Commerce. In 1998, upon completion of his master’s thesis, “The Role of Faith based Institutions in Promoting and Sustaining Local Economies”, he graduated MIT with a Master in City Planning.