Douglas D. Drysdale is a Senior Counsel in Caplin & Drysdale's Washington, D.C. office. He has approximately 50 years of practice experience, primarily devoted to tax matters of all sorts. For more than twenty years, he taught a seminar at the University of Virginia Law School on the procedural aspects of tax practice.
Currently, Mr. Drysdale's practice emphasizes counseling of high net worth individuals, especially those with wealth centered in closely-held business interests, and advising tax-exempt organizations and their related persons on difficult tax issues. For example, in recent years he has obtained an IRS ruling accepting for income, estate, and generation-skipping tax purposes a local court's construction of an ambiguous inter vivos trust; advised a wealthy family on the conversion of their personal holding company to subchapter S status; assisted a large private foundation in resolving successfully (partly through a favorable IRS ruling) a potential excess business holdings tax liability to which it became exposed inadvertently; and advised on the resolution of various self-dealing tax issues for private foundations (especially those affecting a foundation's expectancy in an estate).
Mr. Drysdale has handled, in a planning or litigation context, dozens of matters involving valuation issues. He has also participated in negotiating the resolution of estate planning and other tax malpractice claims against other law firms.