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Douglas A. Pessefall
555 East Wells Street
Suite 1900
Milwaukee, WI 53202-3819
Phone: (414) 978-5534
Fax: (414) 223-5000

Doug Pessefall is a shareholder in the Milwaukee office of Whyte Hirschboeck Dudek S.C. where he represents and advises corporations, partnerships and individuals in connection with complex federal and state tax audits, administrative appeals and tax litigation involving a wide variety of issues. Mr. Pessefall also leads the firm's Tax Exempt Organizations Team. He has more than 20 years professional, legal and management experience working with businesses and tax exempt organizations, having led downtown and economic development efforts prior to joining the legal profession. Mr. Pessefall has also worked with the Office of Chief Counsel for the Internal Revenue Service's Tax Exempt/Government Entities Division in Chicago and the Milwaukee County Circuit Court. He is a frequent speaker and publisher on tax matters.


  • The John Marshall Law School (Chicago), J.D., cum laude; Lead Articles Editor, John Marshall Law Review; Editor, John Marshall Ethics Case Notes & Comments; Francis D. Morrissey Scholar
  • University of Dayton, B.A., Political Science


  • State Bar of Wisconsin
  • U.S. Tax Court
  • U.S. District Court for the Eastern District of Wisconsin

Awards & Distinctions

  • Selected for inclusion in The Best Lawyers in America® in Litigation & Controversy – Tax and Tax Law (2013, 2014)
  • Named a "Leading Lawyer" by M, Milwaukee's Lifestyle Magazine (2012-2014)
  • Named a "Rising Star" on the Wisconsin Super Lawyers list (2012)

Representative Work

  • Represented numerous partnerships, corporations and individuals in connection with complex federal, state and property tax audits, criminal tax investigations, summons enforcement, administrative appeals, audit reconsideration and tax litigation before the U.S. Tax Court, U.S. District Court, Wisconsin Tax Appeals Commission and Wisconsin Supreme Court.
  • Represented clients in connection with the reporting of undisclosed foreign bank accounts and assets, including non-filing of the Report of Foreign Bank and Financial Account (FBAR), participation in and opting out of the Internal Revenue Service's 2011 Offshore Voluntary Disclosure Initiative.
  • Represented a real estate investment company in the acquisition of a $16 million commercial property involving senior secured and mezzanine loan financing, and $2 million in syndicated private equity, including equity held by Individual Retirement Accounts.
  • Represented a commercial lender in connection with New Markets Tax Credits and Rehabilitation Tax Credits, including advising the lender on loan structuring and pricing to avoid original issue discount issues, and advising the lender on recapture and placed in service issues arising in a Historic Tax Credit Pass Through Agreement.
  • Represented a Wisconsin real estate developer in connection with $5 million senior housing project utilizing $4 million in Low-Income Housing Tax Credits.
  • Represented a Wisconsin distributor of power generation equipment in connection with the formation of a limited partnership to develop a landfill gas electric generation facility and qualify for Renewable Electricity Tax Credits.
  • Represented companies in connection with the merger, acquisition, purchase, and/or proper classification of assets involving wind turbine, waste reduction, waste treatment, anaerobic digester, paper waste conversion, private utility, recycling, nuclear, ethanol and/or water distribution facilities.
  • Represented family-owned real estate partnerships in connection with the recapitalization and contribution of ownership interests to a real estate holding company that would simplify the gifting of ownership interests, including advising the client on the rules governing technical terminations and Low-Income Housing Tax Credits.
  • Represented numerous clients in tax-deferred exchanges involving real estate and personal property, including reverse exchanges, master exchange programs and the use of single member limited liability companies.

Professional Associations

  • State Bar of Wisconsin, Taxation Section Board of Directors, Immediate Past Chairperson
  • American Health Lawyers Association
  • Wisconsin Nonprofits Association
  • Milwaukee Bar Association, former Chair Taxation Section
  • Milwaukee Tax Club
  • Wisconsin State and Local Tax Club
  • Institute for Professionals in Taxation
  • Wisconsin Association of Assessing Officers
  • American Bar Association

Community Involvement

  • Future Milwaukee Class of 2008
  • North Avenue Community Development Corporation, former member Board of Directors
  • Milwaukee Kickers Soccer Club, Inc., former member Board of Directors and Treasurer
  • Tosa Baseball League, Umpire
  • Tosa Kickers Soccer Association, former Coach
  • Modjeska Youth Theatre, Inc., former member Board of Directors
  • Iron Angels, Inc., former member Board of Directors

Teaching Positions

  • Advisory Board Member, CCH Journal of State Taxation
  • Faculty, University of Wisconsin Law School, Administrative/Local Government Proceedings unit of the Lawyering Skills Course, January 23-25, 2013.
  • Former Adjunct Professor, University of Wisconsin-Milwaukee School of Business Administration, teaching "Multistate Income Taxation"

Articles and Presentations