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Robert M. Romashko

Robert M. Romashko

Associate
Chicago
office: 312.662.4665
fax: 312.655.1501
Overview

Robert counsels for-profit and non-profit clients on tax planning and compliance issues and represents them before federal and state taxing authorities and in court.

Robert also defends clients in white collar matters, government investigations, and related litigation. As an advisor and representative, he understands that each client’s situation is unique and requires a solution tailored to the client's individual business needs and goals.

Robert is a former senior attorney with the U.S. Internal Revenue Service (IRS) Office of Chief Counsel. As such, he has a unique understanding of how to best navigate government tax agencies, as well as valuable insight into the IRS’ strategies in tax investigations and litigation. In his role at the IRS, Robert litigated cases involving valuation disputes, estate and gift taxation, transferee liability and civil tax fraud. He also advised IRS examination and appeals functions on the conduct of audits and development of cases.

Robert also has experience in:

  • Repatriation of foreign earnings using tax-efficient techniques
  • Debt-equity issues
  • Reconstruction of income via indirect methods of proof
  • Corporate tax shelters
  • Bad debt deductions
  • Federal tax issues in Chapter 7, 11 and 13 bankruptcies
  • Tax consequences of judgments and settlements
  • Research and development credits
  • Passive activity loss

Prior to working for the IRS, Robert was a staff law clerk at the U.S. Court of Appeals for the Seventh Circuit. He has also conducted numerous trainings for the IRS; spoken before the Federal Taxation, Practice and Procedure Division of the Chicago Bar Association; and taught moot court as an adjunct professor at DePaul University College of Law.

Before becoming a lawyer, Robert worked for two years in the nonprofit sector.


Industries

Services

Recognition

  • IRS Office of Chief Counsel Lucite Award, 2013
  • IRS Bronze Litigation Medallion

Education

  • J.D., University of Illinois College of Law
      • Order of the Coif
      • CALI Excellence for the Future Awards in Bankruptcy, Contracts, Criminal Procedure, and Property
  • B.A., Michigan State University

Admissions

  • Illinois
  • U.S. Court of Appeals, Seventh Circuit
  • U.S. Tax Court
  • Wisconsin
  • U.S. District Court, Northern District of Illinois
  • U.S. District Court, Northern District of Illinois (Trial Bar)

Professional Associations and Memberships

  • American Bar Association
  • American Health Lawyers Association
  • Chicago Bar Association, Federal Taxation Committee
  • Federal Bar Association, Section on Taxation
  • State Bar of Wisconsin
Experience
  • Persuaded IRS to completely concede $780,000 in penalties and interest related to final tax return filing for a dissolved entity.
  • Represented client as co-counsel in eight-day trial before United States Tax Court concerning debt versus equity issues under Internal Revenue Code section 385 and write-offs of partially worthless bad debt totaling $92 million over nine tax years.
  • Advised client on tax implications of amended employment contract and how to make I.R.C. Section 83(b) election in relation to stock granted under new employment contract.
  • As co-counsel, obtained favorable results in federal tax audit, reducing total tax and penalties due and obtaining favorable adjustments not initially proposed by examiner in relation to real property disposition.
  • Represented clients before the Internal Revenue Service before both Examination and Appeals.
  • Obtained withdrawal of federal tax lien filed against client in relation to employment tax liabilities.
  • Advised multiple nonprofit clients on obtaining federal tax exempt status.
  • Advised nonprofit clients on state tax and compliance issues related to matters including real property transfers and joint ventures.
  • Defended multiple clients in Securities Exchange Commission investigations regarding accounting and investment practices.
  • Advised nonprofit clients on various state and local tax compliance issues, including applicability of state transfer and real property taxes, and effects of state tax compliance issues on local tax.
  • Counsel healthcare clients in False Claims Act and similar investigations.