Chester H. Hobbs, IV, Esq.


Chester manages the Estate Planning, Estate and Trust Administration, and Bankruptcy departments of the firm. He also regularly advises clients regarding the establishment of business entities, including corporations, limited liability companies and partnerships. He represents businesses and individuals in estate planning and business continuation issues, as well as representing individuals and businesses in bankruptcy and credit workout situations. He frequently drafts Deeds to transfer real property when related to his other practice areas. In addition, he is a recognized title agent for Chicago Title Company, and is also a certified mediator for the Orphans’ Court for Baltimore County.

Prior to joining HWK Law Group, Chester was with Bodie, Dolina, Hobbs, Friddell, and Grenzer, P.C. from 1986-2024, and served as President of the firm from 2019 to 2024. From 1990 to 2003, Chester was a member of the faculty of Stevenson University (formerly Villa Julie College) in the Paralegal Department. He has lectured at seminars sponsored by the National Business Institute and has been a guest speaker at numerous educational events sponsored by accountants and financial planners in and around Baltimore. Mr. Hobbs frequently appeared as a guest on the Savvi Investor radio and television series.

When not practicing law, Chester enjoys playing golf and tennis, cycling, hiking, skiing, and playing guitar.

Maryland Bar
Washington D.C. Bar

University of Baltimore,  J.D. and LL.M in Taxation

Awards & Recognitions
10-Year Pro Bono Award, Maryland Volunteer Lawyer Service
Pro Bono Attorney of the Year, Baltimore County Bar Association
Client Distinction Award,
Named Maryland Super Lawyer, Maryland Super Lawyers
Named Super Lawyer, Thomas Reuters
Certificate of Appreciation, United States Bankruptcy Court
Nationally Ranked Top 10 Attorney Award, National Academy for Bankruptcy Attorneys
Client Satisfaction Award, American Institute for Bankruptcy Attorneys
AV Rated, Martindale-Hubbell
MVLS 10-Year Recognition

Professional & Community Affiliations
Baltimore County Foundation’s Professional Advisor Recognition Society
Rotary Club of Towsontowne-Hunt Valley, President-Elect
Chesapeake Planned Giving Council, Member
Maryland Estate Planning Council, Member
Baltimore Estate Planning Council, Board Member
Kennedy Krieger Planned Giving Council, Past Member
Baltimore County Bar Association Estates & Trusts, Past Chairperson