Mr. Brennan graduated from the University of Maryland School of Law, and began to practice law in 1992.  Mr. Brennan began his practice of law at a large firm in Baltimore, where he remained until April, 1995.  In 1995, Mr. Brennan left the large law firm to join Kathleen Howard Meredith and Charles E. Iliff, Jr., the co-founders of the firm which is now named Iliff, Meredith, Wildberger & Brennan, P.C., in the formation of a small litigation firm where his primary areas of practice concentration would be professional liability defense of attorneys in civil and disciplinary cases and appellate litigation.  Mr. Brennan became a shareholder of the firm which is now named Iliff, Meredith, Wildberger & Brennan, P.C. in 2003.  Mr. Brennan is currently the managing shareholder of Iliff, Meredith, Wildberger & Brennan, P.C.

Since 1992, Mr. Brennan’s practice has emphasized representation of attorneys in  defense of professional liability civil cases and attorney discipline cases.    Mr. Brennan’s practice also regularly includes appellate litigation, insurance coverage disputes and litigation, and commercial and business litigation.   Mr. Brennan has been counsel in many cases that have contributed to the development of the law, in his various areas of practice, through reported opinions. 

Mr. Brennan is active in the legal community and in the community at large.  Mr. Brennan has served as Treasurer (2010-11), President-Elect (2011-12) and President (2012-13) of the James C. Cawood, Jr. American Inn of Court, and he has been a member of the Inn’s Board of Trustees since 2008.  Mr. Brennan is a member of several ABA committees and sections, including ABA Lawyers Professional Liability Consortium, ABA Center for Professional Responsibility, ABA Torts and Insurance Practice Section, Professionals’, Officers’ and Directors’ Liability Committee, and ABA Litigation Section, Appellate Practice Committee.  Mr. Brennan is also active in the Maryland State Bar Association, as a member of the Maryland Pattern Jury Instruction, Civil, Committee, and as a Member of the Litigation Section, Appellate Practice Committee.  Mr. Brennan has also served on the Professional Ethics Committee of the Bar Association of Baltimore City.   In terms of his involvement in the community at large, Mr. Brennan has served for many years as a member of the Board of Directors of the Arc Central Chesapeake Region, a non-profit organization that provides services to people with intellectual and developmental disabilities and their families, and he has also served as an officer of this organization.  Mr. Brennan has also served on the Board of Trustees of St. Margaret’s Day School and as a member of the Vestry of St. Margaret’s Episcopal Church.

Mr. Brennan has written articles or presentations on a number of topics, including “Role of Expert Witnesses in Legal Malpractice Cases,” “Fee Disputes: Things to Think About,” “Settlement Recommendations: High Risk Behavior for Maryland Attorneys,” “Ex Parte Communications with Former Employees of an Adverse Party: Maryland Lawyers Proceed at Their Own Risk,” “Risk Management for Attorneys,” “Expert Testimony Under Maryland and Federal Law,” “Perils of E-Discovery,” and “Managing Your Statute of Limitations (and What to Do When You Screw Up).”