Gould + Ratner




Chair, Tax and Wealth Transfer Practice

Jennifer Tolsky advises businesses, families and individuals in complex estate planning, wealth transfer, business succession planning and taxation matters. Jennifer’s experience includes analyzing income tax and estate tax implications, and reviewing business transactions to determine the income tax implications. Her wealth and succession planning experience strikes the strategic balance between executing her client’s vision and providing tax efficient solutions.

Before joining Gould & Ratner, Jennifer was a tax associate with RSM US LLP, where she prepared complex individual, trust, partnership and gift tax returns.

Jennifer is an active member of the Chicago Bar Association, Illinois Bar Association and the Chicago Estate Planning Council (CEPC). She also frequently writes articles related to changes in tax law.

Jennifer earned her J.D. from UIC John Marshall Law School, and received her bachelor’s degree in economics from the University of Illinois at Urbana-Champaign.

Jennifer is a Certified Public Accountant and is fluent in Korean.


Connect with Jennifer

(312) 899-1648 Office
Jennifer Tolsky
Rated by Super Lawyers

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Connect with Jennifer

(312) 899-1648 Office
Jennifer Tolsky
Rated by Super Lawyers

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  • University of Illinois Chicago School of Law, J.D., 2008
  • DePaul University, Accounting Studies (non-degree), 2010
  • University of Illinois at Urbana-Champaign, B.A., Economics, 2005

Bar Admissions

  • Illinois

Key Cases or Transactions

  • Represented a family estate in planning strategies, including the sales of interests in entities and creation of trusts beneficial for estate tax purposes.
  • Represented an oil and gas company in a restructure of certain tax benefits.
  • Represented a family estate in the simplification of business holdings and estate planning.
  • Represented various high net worth individuals in drafting estate plans, including revocable trusts, wills and powers of attorney for property and healthcare.
  • Advised one of the nation’s largest operators for barges in tax structure and tax research related to purchases and acquisitions.
  • Advised various entities with respect to the BE-10 disclosure requirements.
  • Represented several high net worth individuals in the creation of private foundations and charitable trusts, including ensuring they meet certain requirements under the IRS.
  • Assisted a high net worth individual with navigating 1031 exchange requirements.
  • Represented a Chicago-based digital healthcare agency in its sale to a global commercialization partner for the life sciences industry.


More than just legal advisors, our lawyers consistently demonstrate the care and commitment that set us apart from much larger law firms.