Bobbe Hirsh

Bobbe Hirsh

Of Counsel


Bobbe Hirsh concentrates on matters of U.S. federal and international tax law. She has over 35 years of experience providing tax advice to U.S. and foreign-based clients on a wide variety of matters, including structuring U.S. and foreign business operations, domestic and international mergers, acquisitions, start-ups and divestitures, U.S. and cross-border financings, joint ventures, transfer pricing and tax treaties. In addition to tax planning and advice, Bobbe represents clients at all levels of tax controversy, including audit, appeals, rulings, closing agreements, competent authority proceedings and litigation.

Bobbe’s practice includes advising on the taxation of alternative risk and captive insurance arrangements. She counsels both businesses and groups of insureds seeking to create their own insurance programs, insurers desiring to provide reinsurance programs for their producers, insurers looking to enter into various offshore arrangements for the pooling of risks and captive managers with respect to conducting operations in compliance with tax requirements. Bobbe has served as a tax advisor to the Commonwealth of Puerto Rico and its Office of Commissioner of Insurance, including assisting in the drafting of its tax-related law and regulations for international insurance operations. She also has advised many of the companies licensed under this regime.

Bobbe has acted as tax counsel to insurance companies on a wide range of financings, such as, offerings of foreign parent guaranteed hybrid step-up notes and the issuance of trust preferred securities and surplus notes in connection with securitizations. In addition to matters relating to income tax, Bobbe advises clients on the federal excise tax on premiums. She has designed compliance programs for brokers, obtained FET treaty exemption closing agreements for foreign reinsurance companies, represented foreign reinsurers and captives on examination by the Internal Revenue Service and received waivers of penalties for foreign insurers’ inadvertent noncompliance.

Prior to joining Skarzynski Black, Bobbe was a partner at an international law firm, headed the international tax practice of the fifth largest accounting firm, and was the manager of tax planning for PepsiCo, Inc.

Bobbe serves on the Boards of Advisors of the Journal of International Taxation and the Journal of Taxation of Financial Products. A frequent speaker for professional organizations, Bobbe is the author of over 50 tax publications, including the seminal captive insurance article for the Journal of Taxation, The Service Clarifies the Facts and Circumstances Approach to Captive Insurance Companies, 100 J.Tax 168 (2004). 

In addition to being an attorney, Bobbe is a Certified Public Accountant.


  • Illinois Super Lawyers, 2005 - 2011
  • Leading Lawyer in Tax Law and International Business and Trade Law, 2004-2015
  • 100 Leading Women Business Lawyers in Illinois, 2008
  • Martindale-Hubbell®, AV Preeminent Rated

  • The New Engine of Growth in Asia Conference: Investment and Technology, ABA Section of International Law (October 2018), Panelist.
  • Proposed Regs. Provide Little Relief to Donees and Heirs of Expatriates, 124 J. Tax'n 60 (2016), Co-Author.
  • Tax-Deferred Reorganization Acquisitions of U.S. Corporations by Foreign Corporations Under Treas. Reg. Sec. 1.367(a)-3(c), Tax Strategies for Acquisitions, Dispositions, Spin-Offs, Joint Ventures, Financings, Reorganizations and Restructurings, Practicing Law Institute (2010, revised through 2015). PLI Course Handbook No. 948, Co-Author.
  • New Reporting Obligations for Foreign Partnerships Require Careful Planning, Tax Planning for Domestic and Foreign Partnerships, LLCs, Joint Ventures & Other Strategic Alliances, Practicing Law institute (1999, revised through 2015). PLI Course Handbook No. 456, Co-Author.
  • PLC Cross Border Handbooks: Tax on Corporate Transactions, United States Chapter (Practical Law Company 2006/07, 2007/08, 2009/10, 2010/11), Co-Author.
  • The American Assault on Tax Havens—Status Report, 44 Int’l Law. 1141 (2010), Co-Author.
  • PLC Cross Border Handbooks: Tax on Finance Transactions, United States Chapter (Practical Law Company 2009/10). Prac Co-Author.
  • Planning for Outbound Transfers under The New Sec. 367(a) and Sec. 367(b) Regulations, Tax Strategies for Acquisitions, Dispositions, Spin-Offs, Joint Ventures, Financings, Reorganizations & Restructurings, Practicing Law Institute (2001, revised 2002 through 2009). PLI Course Handbook No. 516, Co-Author.
  • IRS Ramps Up Audit Initiative on Withholding From Foreigners, 109 J. Taxt'n 350 (2008), Co-Author.
  • Service Issues Guidelines for Repatriation Tax Holiday, 9 Prac. U.S./Int'l Tax Strategies 18, 1 (Oct. 2005), Co-Author.
  • The Service’s Guidelines for Enjoying the Section 965 Foreign Tax Holiday, 103 J. Tax'n 208 (2005), Co-Author. 
  • AJCA Replaces Tax Incentive for Exports with a Domestic Production Tax Break and a One-Time DRD, 102 J. Tax'n 6 (2005), Co-Author.
  • The Service Clarifies the Facts and Circumstances Approach to Captive Insurance Companies, 100 J. Tax'n 168 (2004), Co-Author.
  • The NAFTA Guide, (Harcourt Brace) (1995), Co-Author.

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