Grant McCorkhill is a partner in Holland & Knight's Chicago office. He specializes in representing privately held companies, trustees and lenders in all aspects of ESOP transactions. He has worked for many years representing companies and ESOP trustees in structuring, negotiating and closing ESOP transactions. He also represents both lenders and borrowers in basic and advanced corporate finance transactions and ESOP loan transactions, including single bank and syndicated transactions for asset-based, structured financing and venture capital transactions. He works in a wide variety of industries, including banking, manufacturing, professional service corporations, healthcare companies, government contractors and franchisees. He frequently speaks at ESOP conferences on transaction structuring, fiduciary issues and ESOP finance transactions.

Recent Transactions.

  • Representation of an ESOP trustee in connection with the ESOP becoming the 100% owner of a company through a redemption of all non-ESOP owned shares for $357 million.
  • Representation of a healthcare services company in the structuring and execution of a sale of 100% of the company’s stock to an ESOP for $70 million, with subsequent conversion to an S corporation, in a transaction involving a redemption, ESOP purchase, senior bank financing.
  • Representation of the agent lender in a $190 million senior secured credit facility to a national dental practice management service provider, for purposes of selling the company to an ESOP, in a transaction involving mezzanine debt and subordinated seller financing.
  • Representation of an ESOP trustee in connection with the sale of an ESOP company to another ESOP company for $62 million acquisition of another ESOP company, including a merger and a merger of the ESOP plans.


  • Case Western Reserve University School of Law, J.D.
  • The College of Wooster, B.A.
Bar Admissions/Licenses
  • Illinois
Court Admissions
  • U.S. District Court for the Northern District of Illinois
  • American Bar Association
  • Chicago Bar Association, Employee Benefits Committee
  • ESOP Association, Member of Finance Committee and Member of Interdisciplinary Advisory Committee on Fiduciary Issues
  • National Center for Employee Ownership (NCEO)
  • American Bar Association, Commercial Lending Section
Honors & Awards
  • Debt Financing of the Year, 20th Annual M&A Advisor Awards, 2021
  • ESOP Deal of the Year ($100 Million +), 2nd Annual U.S.A M&A Atlas Award for Middle Markets


Speaking Engagements