Douglas Pessefall
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Douglas A. Pessefall is a shareholder in Reinhart’s Tax, Litigation, and Corporate Law practices. Doug represents and advises taxpayers in connection with state and local tax (SALT) planning; state, local and federal tax controversy; tax exempt organizations; and general business matters. He provides legal representation to clients on the nature or extent of their tax reporting obligations, tax compliance or tax liabilities arising from exemptions, audits, assessments, voluntary disclosures or claims for refund, which include sales and use tax, property tax, ad valorem tax, gross receipts tax, franchise tax and income tax.

Prior to establishing a successful law practice, Doug led community and economic development, public relations and tax recovery initiatives for local governments and worked as an executive director for two nonprofit business improvement districts. He also worked with the Internal Revenue Service Office of Chief Counsel for the Tax Exempt/Government Entities Division in Chicago.

Doug’s collective professional and legal experiences prove to be invaluable to his clients as he brings an in-depth and unique understanding of issues facing them from both sides the table. Doug’s ability to view matters from multiple angles enables him to effectively represent individuals, businesses and nonprofit organizations before state, local and federal tax authorities.

Clients appreciate Doug’s ability to draw on his vast knowledge and experience base to provide creative, cost-effective and practical solutions for a wide array of complex legal issues. In addition to his legal practice, Doug is a frequent speaker and publisher on tax matters.


Education

J.D., cum laude, The John Marshall Law School (Chicago)
B.A., University of Dayton

Bar Admissions

Wisconsin

Court Admissions

U.S. Tax Court
U.S. District Court, Eastern District of Wisconsin

  • Represented property owners in successful challenges to property tax assessments, achieving significant annual tax savings, including a $2.3 million reduction in the assessment of a medical office building based on functional obsolescence, a $4.7 million reduction in the assessment of a multi-family residential rental property when the municipality failed to recognized the purchase price accepted by the U.S. Bankruptcy Court as indicative of fair market value, and a $1.8 million reduction in the assessment of manufacturing property based on functional and economic obsolescence
  • Represented clients in connection with sales and use tax planning, audits and appeals, including creation of wholly-owned or affiliated transportation subsidiaries to allow tax free purchase of motor vehicles used by contract or common carriers; supply companies to allow tax free purchases by real property construction contractors on behalf of exempt organizations; and/or aircraft companies to allow tax free purchases of corporate aircraft for lease to reduce potential business liabilities associated with operation of aircraft and to defer the payment of sales tax
  • Represented clients in connection with compliance and/or reporting of previously undisclosed foreign bank and financial accounts, including participation in and opting out of the Internal Revenue Service’s Offshore Voluntary Disclosure Initiative, and Streamline Domestic Offshore Procedure
  • Represented international air carrier in connection with ad valorem tax audit defense and counterclaim for hub facility exemption
  • Represented Wisconsin-based insurance companies in connection with refund claim litigation involving the calculation of license fees based on gross premiums received
  • Represented Wisconsin trade association in successful effort to obtain an informal prior letter ruling that reversed an administrative decision relating to a multimillion dollar annual sales and use tax issue
  • Represented clients in connection with the preparation and litigation of property tax exemption requests, including property owned and used by colleges and universities in excess of the 80-acre limitation, cemeteries, religious organizations for student housing and hospital for an outpatient medical center
  • Represented numerous partnerships, corporations and individuals in connection with federal and state tax audits, criminal tax investigations, summons enforcement, administrative appeals, audit reconsideration, refund claims and tax litigation before the U.S. Tax Court, U.S. District Court, Wisconsin Tax Appeals Commission and Wisconsin Supreme Court, including issues relating to passive activities, reasonableness of compensation, unreported income and business deductions
  • Represented hundreds of tax exempt and nonprofit organizations in connection with formation, tax compliance and audits, and management and governance issues, including charitable and religious organizations, private foundations, health care and social service organizations, trade associations, social clubs, sports and amateur athletic organizations, arts and cultural organizations, charter schools, community and economic development corporations, affordable housing corporations, governments and other tax exempt organizations

Honors

  • Named to The Best Lawyers in America® in Litigation & Controversy-Tax and Tax Law (2013-2015)
  • Named a “Leading Lawyer” by M, Milwaukee’s Lifestyle Magazine (2012-2015)
  • Named a “Rising Star” by Wisconsin Super Lawyers (2012)

Affiliations

  • State Bar of Wisconsin, Taxation Section Board of Directors, Immediate Past Chairperson
  • 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 Institute of Certified Public Accountants
  • American Bar Association
  • Top 10 State and Local Tax Issues, Reinhart CLE Seminar, November 15, 2016 (Presenter) 
  • Recent Developments in Wisconsin State and Local Tax, Schenck S.C., Webinar, November 8, 2016 (Presenter)
  • Recent Developments for Nonprofit Organizations, Wisconsin Institute of Certified Public Accountants Annual Tax Conference, Milwaukee, November 4, 2016 (Presenter)
  • Clarifying Nexus Confusion and Reviewing Recent Developments, Sales and Use Tax in Wisconsin, National Business Institute, Milwaukee, Wisconsin, November 18, 2015 (Presenter); Middleton, Wisconsin, November 17, 2015 (Presenter)
  • Emerging Tax and Governance Issues for Nonprofit Organizations, Wisconsin Institute of Certified Public Accountants, Waukesha, Wisconsin, November 18, 2015 (Presenter); Eau Claire, Wisconsin, September 16, 2015 (Presenter); Appleton, Wisconsin, September 11, 2015 (Presenter)
  • Unrelated Business Taxable Income and Advising on Operational Issues, Tax Exempt Organizations from Start to Finish, National Business Institute, Pewaukee, Wisconsin, August 11, 2015 (Presenter)
  • Emerging Tax and Governance Issues for Nonprofit Organizations, State Bar of Wisconsin Annual Conference, Lake Geneva, Wisconsin, June 25, 2015 (Presenter)
  • State and Local Tax Updates, Wisconsin State and Local Tax Club, Milwaukee, March 18, 2015 (Presenter)
  • State and Local Tax Updates, Milwaukee Tax Club, Milwaukee, February 9, 2015 (Presenter)
  • Wisconsin Tax Update, Wisconsin Institute of Certified Public Accountants Annual Conference, Milwaukee, November 7, 2014 (Presenter)
  • Wisconsin State and Local Tax Issues that Arise in Deals, Professional Institute of Tax Study, Inc., Milwaukee, October 8, 2014 (Presenter)
  • Reporting Offshore Accounts, 64th Annual Tax School, Taxation Section of the State Bar of Wisconsin, Milwaukee, December 6, 2013 (Presenter)
  • Sales and Use Tax in Wisconsin, National Business Institute, Madison, Milwaukee and Green Bay, October 2013 (Presenter)
  • Nonprofit Governance Issues, Wisconsin Institute of Certified Public Accountants, Madison, October 18, 2013 (Presenter)
  • Tax Exempt Organizations from Start to Finish, National Business Institute, Pewaukee, August 15, 2013 (Presenter)
  • Top 10 State and Federal Tax Issues for Nonprofit Organizations, Wisconsin Institute of Certified Public Accountants, Appleton, May 17, 2013 (Presenter)
  • Top 10 State and Federal Tax Issues for Nonprofit Organizations, Wisconsin Institute of Certified Public Accountants, Madison, November 9, 2012 (Presenter)
  • Policymaking: Nuances of Lobbying, Educating, Advocating – What You Can and Can’t Do From Where You Sit, 9th Annual Wisconsin Comprehensive Cancer Control Summit, March 29, 2012 (Presenter)
  • State and Local Tax Traps, Wisconsin Institute of Certified Public Accountants, March 16, 2012 (Presenter)
  • IRS Attacks on Taxpayers with Offshore Accounts: The Saga Continues, State Bar of Wisconsin PINNACLE Seminar, March 8, 2012 (Presenter)
  • Property Tax Valuation & Exemption: Opportunities and Obligations for 2012 and Future Years, Wisconsin State and Local Tax Club, January 2012 (Presenter)
  • Nonprofit Property Tax Exemption and PILOTs Panel, Wisconsin Nonprofits Association Annual Summit, September 14, 2011 (Presenter)
  • From the State Rotunda to the U.S. Capitol: The Top 10 Tax Issues for 2011 and Beyond, Kiwanis Club of Milwaukee, March 9, 2011
  • Advocacy Nuts & Bolts, Wisconsin Nonprofits Association Annual Summit, May 18, 2010 (Presenter)
  • Illinois to Allow the Organization of Low-Profit Limited Liability Companies, Business Law News (State Bar of Wisconsin), September 2009
  • Wisconsin Tax Updates, Institute for Professionals in Taxation-Milwaukee, June 4, 2009 (Presenter)
  • State Bar of Wisconsin 59th Annual Tax School, Madison, WI, December 2008 (Program Chair)
  • Wisconsin State Tax Update 2008, Professional Education Systems Institute, LLC, September 2008 (Presenter)
  • Wisconsin Property Tax Update, State and Local Tax Club, Inc., Milwaukee, January 2008 (Presenter)
  • What’s It Worth? Practical Perspectives on Charitable Giving, Planned Giving Council of Eastern Wisconsin, Milwaukee, September 2007 (Presenter)
  • Practical Perspectives on Private Foundations, Planned Giving Council of Eastern Wisconsin, Milwaukee, March 2006 (Presenter)