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Deputy City Managers
Chief Deputy City Manager

Wynter Benda, Assistant City ManagerWynter Benda has been an integral part of Team Norfolk for over six years and during that time has taken on many roles within the City Manager’s Office, including working across city departments as an Assistant to the City Manager, leading city departments as the Deputy City Manager for Health, Cultural Amenities and Legislative Services beginning in 2013, and transitioning to Deputy City Manager of Planning and Infrastructure in fall 2016.  

Mr. Benda previously served as Senior Assistant City Attorney for the City of Hampton. He also held the position of In-House Council for the Chesapeake Treasurer’s Office and served as a Judicial Law Clerk for the 7th Judicial Circuit.

Mr. Benda received a Bachelor of Arts degree from Hampden-Sydney College, a Masters of Divinity degree and a Masters of Theology degree from Union Presbyterian Seminary and a Juris Doctor from Regent University School of Law.

Mr. Benda was born in Norfolk and raised in Virginia Beach. He and his wife Shannon and three daughters now call Norfolk home. Mr. Benda is an active member of First Presbyterian Church and spends his free time chasing after his girls. He is well known for his array of bow ties.


Deputy City Managers

Michael GoldsmithMichael Goldsmith served as Chief of Police prior to his appointment as Deputy City Manager overseeing public safety. Mr. Goldsmith began his public service career as a Norfolk Police Officer. Throughout his 27-year career with the Norfolk Police Department he expanded training and implemented national best practices in fair and impartial policing.  He also spearheaded the development of the department’s first Crisis Intervention Team (CIT) and enriched the partnership with the Norfolk Community Services Board. 

Furthermore, Mr. Goldsmith worked collaboratively to enhance the Neighbors Building Neighborhoods program and bolstered community-policing efforts. Under his leadership, the Norfolk Police Department received its first national accreditation through the Commission on Accreditation for Law Enforcement Agencies.  

Mr. Goldsmith serves on several regional and national law enforcement boards. In addition, he served as the law enforcement subject matter expert at the North Atlantic Treaty Organization’s (NATO) Urbanization Experiment at the NATO Defense College in Italy.

Mr. Goldsmith and his wife Karen have 3 children, Zach, Rachel and Ellie.  Mr. Goldsmith loves to vacation at Walt Disney World and spends his free time reading. 


James RogersJames Rogers served as Director of Neighborhood Development prior to his appointment as Deputy City Manager overseeing a portfolio of community-oriented city departments.

Mr. Rogers has more than 20 years of leadership experience in the private and public sector.  For the past 12 years, he has been an integral leader in the City of Norfolk.   As Director of Neighborhood Development, Mr. Rogers increased partnerships and collaboration between city departments, civic leagues and community-based agencies.  He implemented a holistic approach to community relations addressing health, housing and public safety needs of Norfolk neighborhoods.  As Special Assistant to the City Manager, Mr. Rogers built community-based initiatives and increased outreach with Norfolk residents to build trust and engagement.

Prior to Norfolk. Mr. Rogers served as Vice President of Operations for the “Y” of Metropolitan Washington; Executive Media & Public Relations Coordinator and Deputy Director of the Office of Central Services for Prince George County’s Maryland; and Vice President of National Sales for School Specialty, the nation’s largest marketer of non-textbook educational materials.

Mr. Rogers is the 2015 recipient of the American Society of Public Administration Association’s Julian F. Hurst Award for Distinguished Public Service, served on the Mayor’s Commission on Poverty Reduction and currently serves as a board member of the Granby Street YMCA.

Mr. Rogers is a veteran of the U.S. Air Force and recipient of the Meritorious Service Medal for Outstanding Service and Commendation Medal.  

Mr. Rogers lives in Norfolk with his wife, Vickie.  They enjoy traveling and visiting their children and their 5 grandchildren.  


Catheryn WhitesellCatheryn Whitesell
 Catheryn Whitesell has more than 30 years of experience in the public sector.  As Deputy City Manager, Ms. Whitesell oversees Finance and Administration.  Previously, she served as the Chief Solutions Officer of Strategy, Transparency, Innovation and Resiliency in the City of Virginia Beach.  She championed the use of innovation, collaboration and open data within city government and with its citizenry. 

In addition, Ms. Whitesell served as Director of Budget and Management Services for 15 years where she worked collaboratively across city departments to meet their missions and services in the community.  She implemented a Biennial Budget, increased resident engagement in budget development and revitalized the process for performance measurements.

Ms. Whitesell received her Master’s degree in Public Administration from the University of Tennessee and Bachelor of Arts in Political Science from Lenoir-Rhyne College.