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Ryan Holmes represents clients in estate tax planning, probate and guardianship administration, and probate, trust, and guardianship litigation. He also assists clients in both residential and commercial real estate matters.

Ryan represents a number of business owners, entrepreneurs, C-suite executives at public companies, and physicians. Ryan has 20 years of experience in advising clients regarding estate and tax planning, asset protection, and techniques to minimize estate, gift tax, and income tax. Ryan also represents individual executors and trustees, including corporate fiduciaries. He administers trusts and estates at any stage, including through controversies both inside and outside of court. Ryan also assists taxpayers with contested tax matters, including federal and state audits and administrative appeals. Ryan represents clients in several states and around the world and has assisted his global clients with cross-border issues.

Charitable foundations and nonprofit entities seek Ryan’s counsel as they aim to maximize the impact of charitable planning. He utilizes compliant domestic and foreign trust planning to achieve proper asset protection. In addition to planning, Ryan oversees the probate and administration of estates and trusts.

Business and Real Estate

Ryan combines his estate planning practice with the disciplines of business, corporate, and real estate law to assist clients with business structuring, succession planning, and exit strategies for businesses of all sizes. Corporate clients work with Ryan as they tackle merger and acquisition transactions, employment agreements, and buy-sell, operating, and other organizational documentation. His clients represent a wide spectrum of industries, including physicians, media and marketing, transportation and logistics, insurance, investment management, food brokerage, real estate development, industrial and chemical, business consulting, publishing, and retail sales. He serves as “outside general counsel” for several of his business clients.

Ryan also focuses his practice on commercial and residential real estate acquisitions and dispositions, including multifamily apartment buildings, condominium properties, vacant land, office buildings, shopping centers, and hotels. He counsels small and medium-sized businesses with respect to formation and capitalization issues, operating issues, acquisitions, financing, and succession planning.


J.D., Northern Illinois University College of Law, Dekalb, Illinois, 2003
B.A., Knox College, Galesburg, Illinois, 2000


Illinois Super Lawyers “Rising Star” 2014-2017


Chicago Bar Association

Illinois Bar Association

Wisconsin Bar Association

Michigan Bar Association

Chicago Estate Planning Council (CEPC), Public Outreach Committee

American Trial Lawyers Association

Forest Park Chamber of Commerce

Northern Illinois University,College of Law Alumni Council

State Bar Licenses

Illinois, Wisconsin, Michigan, Iowa

Court Admissions

U.S. District Ct., N.D. of Illinois
U.S. Court of Appeals, 7th Circuit
U.S. District Ct., N.D. of Indiana
U.S. Supreme Court
  • Co-Author of “Succession Planning – The Importance of Succession Planning for Closely Held Business Owners” Published in the 2015 Illinois Banker’s Resource Guide (2015)
  • In 2015, Ryan and MacKenzie A. Hyde of Clark Hill PLC updated the chapter entitled “Roth Individual Retirement Accounts” in 2015 Update to the book Retirement Benefits Issues in Estate Planning
  • “Estate Planning For Non-Traditional Families” – DuPage County Estate Planning council (April 12, 2017)
  • “CBA Trust Law Committee Program on Non-Traditional Clients” Co-Presenter (April 10, 2017)
  • Presented “Planning for Non-Traditional Families” at the Michigan Association of CPAs West Michigan Tax Symposium on November 9th at the L.V. Eberhard Center on the campus of Grand Valley State University in Grand Rapids
  • Presented “Planning for Non-Traditional Families” at the Michigan Association of CPAs Small Firm Practitioners Conference on Friday August 19, 2016 in Battle Creek, Michigan
  • Multiple presentations to cpa firms for cpe credit on “Fiduciary Income Tax Return Preparation. Tips and Tricks. (2015-2016)
  • Co-Presenter at “Exit Strategy: Positioning Your Firm, Your Estate, and Your Investment for Success” CoHosted by Clark Hill PLC and The Northern Trust Company (June 5, 2015)
  • Co-Presenter on “Income Tax in Elder Law” at the 2014 IICLE Elder Law Short Course (IICLE 2014)
  • “Estate Planning for Beneficiaries with Special Needs” (2009)
  • Multiple “lunch and learn” presentations to financial advisors, accountants, and other wealth management professionals on estate planning, business succession, and income, gift, generational, and estate tax planning
  • “Tax Issues When Settling Employment Claims – Are Your Settlement Agreements in Compliance?” – DuPage County Employment/Tax Committee Meeting (January 2012)