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Richard A. Sugar organizes the legal affairs of his clients to minimize risks, maximize returns, and preserve wealth. With the benefit of more than 39 years of legal experience, Richard approaches every client engagement providing highly personal service while searching for fresh, innovative ideas to solve his clients’ most pressing problems quickly.  

Richard advises clients in many industries, including professional practices, health care, financial services, technology, manufacturing and wholesale businesses and non-profit organizations.

Richard’s forte is in counseling clients to preserve wealth and afford security to the current generation while planning to pass that wealth to future generations in ways that maximize benefits, minimize costs, and avoid corrupting future generations. Richard has been privileged to advise a number of client families over a span of three generations.

Significant Engagements & Transactions

  • Represented a father and helped him to organize a family enterprise.  Because of careful estate, tax, and business planning, the enterprise successfully transitioned to two sons, after the death of the father, with no disputes involving other family members, no business disruption, and little tax cost.  The engagement continued as the enterprise grew to many times its original size, ultimately being sold to a public company in a heavily negotiated transaction for a great deal of money, and the sons retained key positions with the acquirer.
  • Assisted a first generation family-owned industrial parts distribution company in passing the business successfully to second generation family members, with sound financial and tax consequences and no intra-family controversy.
  • Represented a singularly renowned professional practice that grew from a single professional to a multi-member professional group, creating an equity and compensation structure that balanced interests of founders and newcomers, and furthered the progress of the practice after the founders began to retire.
  • Assisted an entrepreneur in creating an IT company, assisted the entrepreneur in obtaining funding, and negotiated a long term license, support, and development relationship with a public company which is dominant in its industry.
  • Helped an out of state food manufacturer to enter the local regional market, establishing and owning local production facilities.
  • Represented developers and managers of real estate, including shopping centers. Doing so included obtaining financing for the projects, title clearance for the projects, and structuring of ownership for maximum tax advantage.
  • Strategically managed the prosecution of enforcement of restrictive covenants against employees who terminated employment with their employer and then violated their employment agreements by diverting customers and business.
  • Negotiated high level, key executive employment contracts for employees in connection with their employment by public institutions and major public companies, paying attention to such issues as incentive compensation, options, deferred compensation, fringe benefits, and restraints on post-employment behavior.
  • Strategically managed Federal court action against the U.S. Government for breach of a supplier contract.  The strategy not only was successful in favor of the supplier, but the supplier recovered attorneys’ fees from the Government, for the Government’s unreasonable defense of the supplier’s action.
  • Prepared an estate tax return for a wealthy decedent client with a large array of assets, and then defended the tax return at IRS audit.  The audit was unagreed and ended up in tax court, where a favorable result for the taxpayer and the taxpayer’s family, over the issues of valuations and tax deductions, was obtained through a negotiated settlement.

Publications, Recognitions and Speaking Engagements


  • Selected by peers as a Leading Lawyer in: Closely & Privately Held Business Law; Individual and Business Tax Law; Trust, Will & Estate Planning Law (2012-2020)

  • Selected for inclusion in Illinois Super Lawyers in Estate Planning & Probate; Business/Corporate, Mergers & Acquisitions (2005-2013, 2015-2020)

  • Martindale-Hubbell AV Preeminent Rated, Chicago’s Top Rated Lawyers, Business and Commercial (2012); 5.0/5.0 Overall Client Rating –

Professional Affiliations

  • Business Advisors Network, Lake Forest Business Accelerator
  • Monthly Columnist, Chicago Tribune Media Group, A Spoonful of Sugar – Tastings of Money, Taxes, and the Law.
  • American Technion Society – Planned Giving Committee
  • Ann and Robert H. Lurie Children’s Hospital of Chicago Legacy Partners
  • Midwest Young Artists, President Emeritus, Former President, and Board of Directors
  • Formerly Chicago Society of Clubs, Governing Board, Chairman of Community Public School Improvement Committee
  • Formerly Commerce magazine, Small Business Division Editorial Board
  • Formerly Illinois Small Business Growth Corporation, board of directors (nominated by Governor Thompson)
  • Formerly Independent Business Association of Illinois, Executive Vice President and Board of Directors
  • Formerly U.S. Securities and Exchange Commission, Government Business Forum on Small Business Capital Formation, Delegate
  • Formerly White House Conference on Small Business, Alternate Delegate
  • Formerly Illinois Lieutenant Governors Conference on Small Business, Delegate and Legal Counsel