Steven A. Felsenthal

Firm: Raines Feldman Littrell LLP.
Location: Chicago - IL

  • 30 North LaSalle Street, Suite 3100
    Chicago, Illinois 60602
  • Tel : (312) 704-9400
  • Fax : (312) 704-2180

Steven A. Felsenthal advises closely held companies, their owners, and their senior executives in virtually every aspect of their business and on personal tax and estate planning issues. His primary areas of focus, for the entirety of his career, have been income tax planning and controversies, sales and acquisitions, debt restructuring, estate planning, strategic planning, and real estate transactions (with a special focus on the acquisition, development and financing of subsidized housing.

Many of Steve’s clients have been with him for more than thirty years. His breath of experience in many facets of the law allows Steve to bring a unique perspective to creatively and effectively solving his clients’ problems. Steve has also served as an expert witness in cases involving tax disputes and accountant and attorney malpractice actions.

Steve continues to counsel many of the same clients he started advising more than three decades ago, as well as succeeding generations and successors in interest.


  • J.D., Harvard Law School
  • B.A., University of Illinois (Urbana),
      High Honors, Phi Beta Kappa

Honors & Awards

  • Premier Tax Lawyers – Exclusive Featured Attorney for Chicago 2020-2024
  • Martindale-Hubbell AV Preeminent Rated – Chicago’s Top Rated Lawyers, Business and Commercial
  • Leading Lawyers – Selected by peers in: Business and Individual Tax Law; Trust, Will & Estate Planning Law; Closely & Privately Held Business Law (2012-2018).  Chosen by peers as among top ten tax lawyers in Illinois, May 2019
  • Super Lawyers – Selected for inclusion in Illinois Super Lawyers 2005 – 2007, 2009 – 2012,  2023 – 2024
  • Leading Lawyers Magazine – Profiled in cover story, “Steven Felsenthal-Much More Than Just a Tax Lawyer,” August 2018


  • American Bar Association
  • Illinois State Bar Association
  • Chicago Bar Association
  • Chicago Council of Lawyers
  • Chicago Estate Planning Council


  • Represented substantial privately held agricultural company in structuring sale of business divisions.  Obtained an IRS private letter ruling for tax-free split-off of the two divisions and then handled tax planning and negotiation in subsequent sale of spun-off divisions to publicly traded strategic purchaser.
  • Obtained an IRS private ruling allowing a tax-free non-pro rata split off of two family owned businesses due to personality differences among third generation siblings.  Following split off, retained over long term for general corporate and tax representation by one company and numerous family members.
  • Represented manufacturing company in $35 million sale to strategic public buyer while retaining certain factories, including pre-sale restructuring to minimize state income taxes on transaction.  Assisted in subsequent sale of retained factories.
  • Defended a manufacturing company in IRS audit that resulted in U.S. Tax Court litigation in which adjustment for treatment of expenses related to product prototypes would have resulted in a $2.5 million adjustment and a change in accounting method that would have negatively affected the competitive position of the business going forward.  Resolved without trial for $35,000 without change in accounting method.
  • Advised partners in real estate partnership on capitalization of existing mortgage debt, structuring transaction so as to reduce taxable income from cancellation of indebtedness.
  • Defended real estate developer in IRS audit that resulted in U.S. Tax Court litigation in which his status as a qualified real estate professional for purposes of the passive activity loss rules was challenged.  Developed a strategy at the audit stage that resulted in settlement of a $6 million adjustment for $6,000 without trial.
  • Testified as expert witness about standards of tax practice in attorney malpractice case arising out of promotion of offshore trust tax shelter strategy.
  • Testified as expert witness about standards of tax practice in multiple accountant malpractice cases related to Son of BOSS and similar tax shelter transactions.  Assisted defense counsel in developing strategy that resulted in advantageous settlements for client.
  • Assisted manufacturing company in tax and corporate structuring for expansion of
  • Represented chief executive officer in negotiation of advantageous employment agreement with public consumer products company.  Advised company on tax and restructuring issues in face of financial difficulties.

Estate Planning and Administration

  • Counseled estate on treatment of investment in Madoff ponzi scheme for federal income and estate tax purposes.
  • In connection with transaction to take private a manufacturing company, integrated estate planning for principal shareholders into the transaction in order to pass ownership of the company to next generation at significant estate and gift tax savings.

Represented numerous wealthy families in estate and tax matters and family relations issues

Raines Feldman Littrell LLP.

Tax planning has been a core strength of the legal services provided by Raines Feldman Littrell LLP. The firm’s tax attorneys draw on broad practical experience and deep technical knowledge to structure tax-efficient transactions for clients. The tax group helps clients effectively respond to audits and, if necessary, pursue administrative appeals and tax litigation.

We know that tax efficiency can affect our clients’ return on investment and that strategic tax planning is essential to giving our clients the best opportunity to succeed in their businesses. We advise our clients in all aspects of the business lifecycle from formation to operations and expansion to sale and restructuring or even retirement and succession. We believe that our clients are best served by involving our tax attorneys early in the process of planning transactions. Our approach is to explain the tax consequences of our clients’ various business decisions so they may choose the best way to achieve their business goals with the minimum tax burden. Because our advice is both technical and practical, our clients have learned to call us first – while the deal is still in the conceptual stage.

As part of our integrated approach, our tax attorneys work with attorneys from other practice areas to address all types of business needs. Some common examples include: the financing of subsidized housing projects or the purchase or lease of a factory, the purchase or sale of a business, the design of a family business succession plan, and the structuring of the settlement of a lawsuit.

Other law firms turn to Raines Feldman Littrell LLP for tax advice. We serve as tax co-counsel to a number of other law firms that rely on us to help structure and review tax issues for their clients’ transactions as well as litigation settlements. Our attorneys have also served as consulting and testifying expert witnesses in cases involving complex tax issues.

The attorneys of Raines Feldman Littrell LLP have extensive experience in dealing with the IRS. We understand that when the IRS calls, the competitiveness of our clients’ businesses can potentially be at risk. Our clients rely on us for our judgment in understanding when to negotiate with the IRS and when to challenge the IRS in court. We collaborate with our clients and their accountants to help navigate the complexities of the audit and appeal process. We can help prepare for an audit, deal with revenue agents, negotiate a settlement, and, when necessary, develop a strategy for litigation and for taking a case to trial.

We also have deep experience in working through the subtleties of trust law.  Our Estate Planning and Administration attorneys integrate that knowledge with such other areas of the law as asset protection, retirement planning, real estate, business and corporate structures, divorce and family law, charitable organizations and foundations.  We not only stay abreast of current law, as all attorneys are required to do; we also teach – law students, financial planners, and other lawyers.

We know what wealth transfer methods work most effectively. We also understand how to shepherd complex estates through the probate courts or an IRS audit.  That experience enables us to work efficiently and effectively, drawing on the skills of our corporate attorneys, our bankruptcy attorneys and our litigation attorneys, as needed.

Estate planning can involve a variety of sensitive family situations ranging from multiple marriages, feuding children, disappointed parents, great expectations and brutal economic realities.  To deal with such situations, our Estate Planning and Administration lawyers go beyond our technical knowledge and considerable experience, bringing compassion and understanding in helping our clients find solutions that feel right for them. Through our technically sophisticated planning, we help our clients minimize the chances of their well-meaning intentions fostering family dissension, or, worse, litigation.

Each of our Estate Planning and Administration attorneys has become a trusted advisor for his or her clients and their families. Beyond wills, trusts, and tax advice, the families we serve have relied on us for counseling across multiple generations.  In bad times, we have helped our clients cope when things go wrong with failing businesses, failing marriages and failing health.  In good times, we advise our clients on growing, preserving and making productive use of their wealth and in creating charitable and educational legacies that embody their families’ values.

Because of the way the firm is organized, we provide a far more holistic approach to the representation of its clients than many other law firms. This results in greater efficiencies and far more effective representation than firms that are organized with silo-ed practice areas.