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Clayton H. Hale, Jr.

Partner and Co General Counsel

Clayton H. Hale, Jr. joined Mackenzie Hughes in 1974 and concentrates his practice in the areas of, business, tax and health care law. His tax and accounting background enables him to assist the firm’s clients in planning and structuring sophisticated acquisition and divestiture transactions; structuring employee benefit plans to comply with the complex ERISA rules and regulations; and planning for the transition of business ownership and preservation of accumulated wealth through sophisticated estate planning. Clayton also renders tax opinions in support of tax exempt bond financings. Having represented numerous members of the medical community, Clayton has developed an expertise in health care law to assist his clients in complying with the rapidly expanding body of law regulating health care compliance and fraud and abuse. The primary focus of Clayton’s practice is to assist clients in planning business transactions that comply with the applicable rules and regulations. However, for those who have not properly planned, Clayton’s extensive knowledge and expertise enable him to provide valuable assistance with state and federal tax, Department of Health, Department of Labor and other regulatory audit issues.

Clayton is also a member of the firm’s immigration law practice group where he counsels individuals and business entities regarding federal US tax regulations impacting their immigration status. Clayton served for twelve years as a member of the firm’s executive committee.

In addition to representing clients, Clayton serves as Co General Counsel to the Firm.  In this capacity, he focuses on advising the Firms attorneys on complicated ethical and professional issues.

When Clayton has a few moments to spare, he spends his time golfing, skiing and sailing.

  • Spent six years as a Tax Specialist in Coopers & Lybrand’ New York City Tax Department providing tax planning for large corporations, partnerships, private foundations and high net worth individuals
  • Represented local savings bank in its conversion to stock form bank, formation of bank holding company, acquisition of commercial banks and eventual sale to a large regional bank
  • Represented large corporate clients in the drafting and IRS qualification of defined contribution retirement plans including ESOPs
  • Represented clients in drafting non-qualified retirement plans for highly compensated executives including IRC Section 457(f) plans for executives of credit unions and other tax-exempt entities
  • Drafted organizational documents for all forms of business entities and not-for-profit organizations
  • Advised on the tax planning for the restructuring of several large engineering firms
  • Successfully appealed as a violation of the interstate commerce clause the imposition of New York Sales Tax on entire cost of hazardous waste disposal services performed for a New York plant of a multinational, Virginia corporation where a large portion of the services were performed out of New York State.
  • Represented several fraternities in tax planning for the forced sale of their chapter houses to a local college to ensure the proceeds of the sale would be received tax free. Established charitable foundations for the purpose of utilizing the sales proceeds to support the educational activities of the continuing chapters.
  • Represented numerous medical groups in all phases of their businesses, including advising on the Stark and Anti-Kickback regulations applicable to Medicare and Medicaid services and the purchase and sale of medical practices
  • Assisted numerous physicians in negotiating their first employment contract with their chosen medical group
  • Provides assistance to trust and estate attorneys on specialized tax issues involved in minimizing estate and gift taxes and administering estates and trusts
  • Provides advice to partners and partnerships on tax planning for the purchase and sale of partnership interests and other partnership transactions
  • Provides services in assisting with the audits of business entities and personal income tax returns and structuring payment arrangements for delinquent taxes


  • American Bar Association
  • New York Bar Association
  • Onondaga County Bar Association



  • Served on Executive Committee of Tax Section of New York Bar Association
  • Served on various committees of Onondaga County Bar Association
  • Frequent lecturer at New York Bar Association CLE programs
  • Lectured on Health Care topics at CLE programs sponsored by National Business Institute
  • Served twelve years on Mackenzie Hughes LLP’s Executive Committee
  • The Best Lawyers’ Syracuse Tax Lawyer of the Year 2011
  • The Best Lawyers in America, Tax Law, thirty-one years (1987-2018)
  • Martindale Hubbell “AV” Peer Review Rated for Very High to Preeminent Ethical Standards and Legal Ability
  • Selected by peer review for inclusion in Super Lawyers Directory 2007-2012


  • Dartmouth College, AB 1964
  • Syracuse University Graduate School of Business, Finance 1965
  • Syracuse University College of Law JD 1968
  • New York University School of Law LLM Taxation 1974
  • Pace College -Accounting 1968-1973


  • New York State Bar
  • United States Tax Court
  • New York State Certified Public Accountant


Seven Mackenzie Hughes Attorneys Recognized as “Best Lawyers in America”

SYRACUSE, N.Y. – Mackenzie Hughes LLP is proud to announce that seven of its attorneys have been named to the 2018 edition of Best Lawyers in America, the oldest and most respected peer-review publication in the legal profession. Recognized for their work: Clayton H. Hale, Jr., tax; Stephen T. Helmer, commercial litigation, insurance law, personal…

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Eight Mackenzie Hughes Attorneys Recognized as “Best Lawyers in America”

Mackenzie Hughes LLP is proud to announce that eight of its attorneys have been named to the 2016 edition of Best Lawyers in America, the oldest and most respected peer-review publication in the legal profession. Recognized for their work: Clayton H. Hale, Jr., Tax; Elizabeth A. Hartnett and Gay M. Pomeroy, Trusts and Estates; Stephen…

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Mackenzie Hughes LLP Attorneys Recognized

Mackenzie Hughes LLP is pleased to announce that eleven of its partners have been named as Super Lawyers in the 2011 edition of New York Super Lawyers Upstate magazine. The list includes: Clayton H. Hale, Jr., Tax; Elizabeth A. Hartnett, Estate Planning & Probate, Stephen T. Helmer, Business Litigation, Civil Litigation, Defense, Personal Injury; Ami…

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Review Of Partnership And LLC Operating Agreements Needed Prior To January 1, 2018

In the past partnerships and limited liability companies that have elected to be taxed as partnerships[1]  have rarely faced an Internal Revenue Service (“IRS”) audit. In part, this is because of the administrative burden faced by the IRS in attempting to collect tax resulting from partnership audit adjustments. The current partnership audit scheme requires partnership…

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2015 Action Required To Maintain Qualified Status Of Prototype Defined Contribution Plans

Maintaining up to date documentation for your retirement plan is extremely important and not something employers should take lightly. During a plan audit the first thing the IRS auditor asks for is a signed copy of the Plan Document with all amendments. If these do not contain provisions timely reflecting the latest legislative and/or regulatory…

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Excluding Gain on the Sale of a Home

As the size of a family increases, families traditionally seek to replace the home they are outgrowing with a larger one. As time goes by and parents become empty nesters it is not uncommon for thoughts to turn to downsizing or perhaps becoming snowbirds and moving to a warmer climate. These, as well as other…

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