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Robert A. Bedore

Bob Bedore is a tax lawyer with extensive experience representing both business and individual taxpayers at every phase of the administrative and judicial tax controversy process. Bob’s clients include large multinational public and privately-held companies subject to the IRS Large Business and International (LB&I) examination program, partnerships and joint ventures, entrepreneurs, affluent families and individuals, trusts and estates, and tax exempt organizations, and his competencies run the gamut, from audit through administrative appeals and post-appeals mediation of contested tax disputes, at trial when tax litigation becomes necessary, obtaining private letter rulings and all forms of technical guidance and advice from the IRS National Office, negotiating compromised alternatives to the immediate and enforced collection of unpaid tax assessments under threat of federal tax lien, levy, asset seizure or forfeiture, and the abatement of civil tax penalties and additions to tax.

Bob has achieved notable recognition within the legal and professional tax community including being recognized as a leader in Chambers USA: America’s Leading Lawyers in Business (recommended in “Tax”) since 2008, being recommended in the 2014 edition of The Legal 500 United States, being included in the Leading Lawyers Network (Tax Law: Business), and being AV Peer Review Rated, Martindale-Hubbell’s highest peer recognition for ethical standards and legal ability.  

Bob is a former IRS senior trial attorney with the Office of Chief Counsel, and has been a Certified Public Accountant in the state of Illinois since 1975. Bob also is a member of the adjunct faculty at Loyola University’s School of Law, where he has taught coursework in the area of Federal Tax Procedure and Litigation for more than 20 years. 

Bob received his Juris Doctor degree in 1980 from DePaul University College of Law, and his Bachelor of Science in Commerce (Accountancy) degree with highest honors in 1975, also from DePaul University. Bob is admitted to practice in Illinois, the United States Tax Court, the United States Court of Federal Claims, the United States District Court for the Northern District of Illinois, the Seventh Circuit Court of Appeals and the Supreme Court of the United States.

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For the past 30 years, Bob has managed the resolution of literally hundreds of federal income, estate, gift and employment tax cases involving an array of highly complex factual and legal issues, and the collective exposure to additional tax, penalties and interest in excess of $10 billion. The following is a list of representative matters which Bob has handled:

  • H Group Holding, Inc. and Subsidiaries, formerly HG, Inc. and Subsidiaries, et al. v. Commissioner of Internal Revenue, T.C. Memo. 1999-334. Tax Court memorandum opinion resolving IRS allocation of income issues in connection with the use of Hyatt trade names and marks, and management services provided to foreign subsidiaries. 
  • Estate of A.N. Pritzker, Deceased, Jay A. Pritzker, Executor of Estate of A.N. Pritzker, Deceased v. Commissioner of Internal Revenue, United States Tax Court Docket No. 16867-90. Pre-trial settlement of estate and correlative income tax issues involving IRS determinations related to grantor trust income adjustments under the provisions of I.R.C. sections 671, 674 and 675, grantor trust income adjustments due to indirect transfers under the provisions of I.R.C. section 679, and Subpart F income adjustments under the provisions of I.R.C. section 7701.
  • Continental Illinois Corporation v. Commissioner of Internal Revenue, T.C. Memo. 1989-636. Tax Court memorandum opinion addressing whether the Commissioner abused his discretion under I.R.C. section 446(b) by determining that the bank’s income tax accounting method, which was in conformity with financial and regulatory accounting principles, did not clearly reflect interest income with respect to portfolio loans commonly referred to as “CAP Loans” and “Net Loans.”
  • Continental Illinois Corporation v. Commissioner of Internal Revenue, T.C. Memo 1989-468. Tax Court memorandum ruling on hearsay and competency objections raised with respect to various exhibits introduced at trial. 
  • Universal Manufacturing Co., Inc. and Subsidiaries, Successor by Merger of WNC Corp., v. Commissioner of Internal Revenue; Delbert W. Coleman v. Commissioner of Internal Revenue, 93 T.C. 589 (1989). Tax Court opinion dealing with petitioners’ motion for protective order regarding the use of testimony, documents or other information obtained pursuant to an administrative summons served by a special agent of the IRS’ Criminal Investigation Division subsequent to the commencement of the subject Tax Court proceedings.  
  • Edward Vanicek, Deceased, and Sara Vanicek v. Commissioner of Internal Revenue; John B. Moden and Ruth Moden v. Commissioner of Internal Revenue, 85 T.C. 731 (1985). Tax Court opinion involving whether the fair rental value of lodging furnished to petitioners by their employer, the Forest Preserve District of Cook County, Illinois, was excludable from gross income under the provisions of I.R.C. section 119.
  • Representation of multibillion dollar business and personal interests of high net worth ownership group for the past 25 years during the course of an ongoing LB&I examination process and the subsequent administrative resolution of disputed tax issues at IRS Appeals. 
  • Favorable resolution of all primary and alternative issues relating to the deductibility of several hundred million dollars in settlement payments arising out of the failure of a federally chartered banking institution.
  • Acting as principal tax controversy counsel, Bob achieved outstanding compromised settlements and often, 100% concessions from IRS Appeals on hundreds of tax issues involving billions of dollars of asserted deficiencies in tax, penalties and interest; for example:
    • Corporate adjustments to income and related constructive dividend adjustments in the amount of $130 million related to valuation disputes involving the disposition of several medical device manufacturing companies.    
    • Disallowance of $53 million of deferred financing fees, $10 million of loan prepayment penalties/premiums, and $10 million of bridge loan commitment fees incurred in connection with leveraged buy-out transaction. 
    • Disallowance of $100 million of worthless stock and bad debt deductions related to domestic and foreign based subsidiaries, a portion of which was resolved as a result of successful mediation proceedings with IRS Appeals.
    • Adjustments to income in the amount of approximately $70 million related to a dispute arising from the characterization of stock warrants that were issued to our client; it is noteworthy that this significant concession was achieved despite the prior issuance of adverse technical advice by the IRS National Office.
    • Disallowance of approximately $100 million of computer data base maintenance deductions related to the gathering, processing and reporting of personal and financial data for consumer credit evaluation purposes.
    • Negligence and valuation misstatement penalties with respect to a multi-million dollar charitable deduction for the donation of a historic facade easement on a well-known commercial building located in downtown Chicago.   
    • IRS And Virgin Islands Bureau of Inland Revenue determinations with respect to client’s status as a full time bona fide resident of the United States Virgin Islands and the proper sourcing of client's business income as from sources within the USVI resulting in several million dollars in tax savings.
    • Sizable proposed increases to income related to the business and personal income tax returns of a well-known television and film industry personality.
    • Multiple year understatement of income adjustments in excess of $2 million, and related exposure to criminal prosecution and substantial civil tax penalties.
    • Disallowance of depreciation and amortization deductions in the aggregate amount of $163 million with respect to the valuation and amortization of certain intangible assets related to product brands acquired and developed by a client in the smokeless tobacco industry.
    • Adjustments to income in the amount of $365 million related to pre-acquisition net operating losses incurred and accumulated by a major airline carrier.
    • Disallowance of magazine subscription cancellations, newsstand returns and discount deductions in the amount of $72 million related to several widely distributed and well known periodicals.
    • Disallowance of deductions, and correlative constructive dividend and constructive trust distribution adjustments, attributable to insurance premium payments made to Bermuda captive insurance companies in excess of $150 million.
    • Disallowance of deductions in the amount of approximately $250 million related to hundreds of railcar, aircraft, computer, telecommunications and other equipment leasing transactions.
    • Proposed revocation of the tax favored/exempt status of (i) a Foundation established and operated by the family of a well-known, now deceased former major league baseball player, and (ii) a client’s profit sharing plan and related trust agreement.
  • Achieved favorable penalty-free resolutions of employment tax examinations for clients involved in various industries, including the retail and mail order shipping, real estate appraisal, senior living and congregate care, food preparation and delivery, and promotional marketing industries, which involved an IRS determination of the proper employment tax status for several hundred workers as independent contractors (as claimed by the clients) v. common law employees. 
  • Successfully handled numerous requests for the abatement (elimination and/or reduction) of different types of civil additions to tax and penalties, including but not limited to accuracy related, late filing, late payment, failure to pay estimated tax, failure to file income tax and/or informational reporting forms and returns, valuation misstatement, promoter, intentional disregard, negligence and civil fraud penalties.
  • Successful representation of numerous clients who wished to limit their civil liability for past failures to file accurate income tax returns, and those making voluntary disclosures related to previously undisclosed foreign financial bank and similar accounts.