Christopher "Kip" Cawley


I help my clients to develop and implement tax-efficient investments, transactions and structures.

Christopher (“Kip”) advises clients on tax matters relating to private investments, business transactions and structures. He works closely with clients to tailor, and then implement, creative, practical and tax-efficient solutions to complex matters.

Kip represents private investment fund managers in connection with the tax aspects of fund formation, portfolio acquisitions and exits, negotiations with investors, management company operations, compliance and information reporting. 

He also regularly advises investors on tax considerations relating to private investments, including eligibility for benefits under income tax treaties and structuring tax-efficient investments for non-U.S. and U.S. tax-exempt investors.

Kip has extensive experience advising partnerships, LLCs, C corporations, S corporations and individuals on tax considerations relating to domestic and cross-border mergers, acquisitions, restructurings, financings and other business transactions.

Kip also advises clients in cannabis-related businesses on federal and state tax considerations relating to mergers, acquisitions, business structuring and operations, and other related matters.


  • Syracuse University College of Law, J.D., cum laude, 2002
  • Denison University, B.A., cum laude, 1999

Bar and Court Admissions

  • Massachusetts
  • Pennsylvania
  • U.S. Court of Appeals for the First Circuit
  • U.S. Tax Court


  • MDxHealth SA (Nasdaq/Euronext: MDXH), a foreign private issuer, in its acquisition of the OncoType DX Genomic Prostate Score business from Exact Sciences Corporation (Nasdaq: EXAS) for cash and equity consideration of up to $100 million, including a multi-year earn-out arrangement.

  • Served as a legal extern to the Hon. Susan Pierson Sonderby of the U.S. Bankruptcy Court for the Northern District of Illinois.


  • Massachusetts May “Decouple” From Section 280E June 16, 2022
  • EIN Processing on Hold April 9, 2020
  • FBAR Filing Deadline: October 15, 2018 September 25, 2018
  • Cayman Islands FATCA/CRS Reporting Deadlines Extended May 31, 2018 

Honors & Involvement

  • The Best Lawyers in America (2023)
  • Boston Bar Association Tax Section, Steering Committee Member (2015-2017), Federal Tax and Business Transactions Committee Co-Chair (2015-2017)
  • Massachusetts Bar Association Taxation Law Section Council, Council Member (2011-2017)
  • Boston Bar Association, Member
  • Massachusetts Bar Association, Member
  • American Bar Association, Member

Speaking Engagements

  • Panelist, "Tax Reform Update," The Concord Vine (April 2018)
  • Panelist, "Tax Update," Small Business Institute Investor Alliance Pre-conference Luncheon, Foley Hoag (February 2018)
  • Panelist, "Partnership Audit Reform and Private Funds," American Bar Association (September 2016)
  • Moderator, "Offshore Asset Disclosure: Practical Tips for the Unwary," Massachusetts Bar Association (May 2016)
  • Panelist, "A Quick Spin Through Spin-Offs," New England M&A Forum, Foley Hoag (April 2016)
  • Panelist, "Tax Law Update (PATH Act of 2015)," Boston Bar Association (February 2016)
  • Panelist, "An Introduction to the Practice of Tax Law," Boston Bar Association (January 2016)
  • Panelist, “Covering the Bases: FATCA Resources,” Foley Hoag (April 2014)
  • Speaker, “Getting Ready for FATCA,” Lex Mundi (October 2014)
  • Speaker, “FATCA Compliance for Hedge Fund Managers,” Financial Executives Alliance (May 2012)    
  • Speaker, “FATCA Compliance for Investment Managers,” Operational Risk Breakfast Club (April 2012)