Back to Professionals

Avi’s practice is focused in taxation. His primary goal is to translate the complex, obscure tax code into business English so that our clients can make intelligent decisions aimed at achieving their financial, social, and personal goals. His clients include established and emerging companies, professional service firms, real estate and private equity investors, and tax-exempt non-profit organizations.

A key focus of Avi’s practice is the tax-efficient structuring of business transactions. Avi advises clients on methods to reduce taxes overall – and to minimize tax risks – in sales of assets and equities, mergers, acquisitions, and reorganizations. Avi addresses the tax treatment of: earn-outs, contingent payments, escrows, security arrangements, management incentives and employee benefits.

Avi provides federal tax advice throughout the lifecycle of a business, at the earliest planning stages, during operations, and at exit. Avi counsels as to tax aspects of employment, hiring and termination; he develops alternatives for equity incentives, deferred compensation, and golden parachute arrangements. At the state level, he advises as to state and local income taxation, nexus and residency issues, and sales and use taxes. Avi also provides advice to private investment entities as well as to real estate investors, and helps to structure Section 1031 like kind exchanges.

Avi represents taxpayers in audits, controversies, and litigation with the IRS and with state tax authorities.

A significant part of Avi’s practice is assisting non-profit associations with tax compliance, corporate governance, and for-profit partnerships. His tax-exempt clients include hospitals and healthcare organizations, museums, churches, temples, schools and universities, public charities, foundations, trade associations, and Native American tribes.

Avi has taught federal taxation in the Graduate Tax Program at the Boston University School of Law and elsewhere, and has served as an expert witness in tax litigation.


Representative Transactions

Corporate, Partnership and Business Transactions

  • Guide aircraft owners and operators in purchasing and managing business airplanes tax-efficiently and in compliance with FCC regulations.
  • Design tax-saving structures for stock sales and asset sales, taxable and tax-free mergers, acquisitions and spin-offs.
  • Plan and execute Section 1031 exchanges of real property.
  • Develop plans for executive compensation, using stock options, restricted stock, dividend equivalent rights, and other forms of deferred compensation.
  • Help a well-known public broadcasting company reorganize, enhancing its endowment function.
  • Help the buyers of a 167-foot yacht avoid state sales tax and maximize federal tax deductions.

International Taxation

  • Help a Boston venture capital firm establish a Luxembourg SICAR to facilitate foreign investment in its U.S.-based medical products companies.
  • Facilitate the expansion of a London-based bicycle distributor into the United States.
  • Organize Asian and European operations for a Boston-based technology company.
  • Provide tax underwriting for an insurance company that insures representations and warranties made by the sellers in corporate acquisitions.

Tax Controversy, Audit and Litigation

  • Successfully resolve a “nexus” issue for a Massachusetts taxpayer with an employee in New Jersey, avoiding New Jersey taxation of the employer’s income.
  • Obtain for a shipyard complete abatement of a six-figure property tax assessment.
  • Defend former Massachusetts residents, now living part-time in other states, against claims that they are still subject to Massachusetts personal income tax.
  • Assist the owner of a major-league baseball team with a tax controversy regarding amortization of player contracts.
  • Obtain a $700,000+ refund for a client who lived in one state but did business in another, where both states asserted primary jurisdiction to impose income tax.
  • Secure a “no change” audit result for an inventor, even though IRS has determined that his deductions should be disallowed as “hobby losses.”

 Tax Exempt / Non-Profit Entities

  • Obtain recognition of tax-exempt and public charity status for several non-profit entities, including museums, schools, churches, athletic clubs and community development groups. Assist with ongoing tax compliance.
  • Provide a formal tax opinion for the Attorney General of Massachusetts that the dissolution of a Boston-based Buddhist temple, and distribution of its assets to its sister temple in Japan, would not jeopardize its public charity status.
  • Help a tax-exempt university develop a cost sharing arrangement with a for-profit research facility.


Work Experience

  • Hinckley Allen
    • Chair, Tax
    • Partner (2012-Present)
  • Davis, Malm & D'Agostine, P.C.
    • Partner and Director (2010-2012)
    • Senior Tax Attorney (2006-2009)
  • PricewaterhouseCoopers, LLP
    • Senior Tax Associate (2005-2006)
  • Sullivan & Worcester, LLP
    • Tax Associate (2002-2005)
  • Houghton Mifflin Co.
    • In-House Counsel (2000-2002)
  • U.S. Bancorp
    • Associate General Counsel (1987-1994)

Honors & Awards

  • Internal Revenue Service, Outstanding Public Service Award

Charitable & Civic Involvement

  • Boston Bar Association, Senior Partners for Justice

Professional Affiliations

  • American Bar Association and Boston Bar Association, Tax Sections. Member

Bar Memberships

  • Massachusetts
  • Oregon
  • United States Tax Court
  • United States Court of Federal Claims

Speaking Engagements

  • Adjunct Professor, Boston University School of Law, Graduate Tax Program; “Federal Taxation II” 2012-2013; “Taxation of Individuals in Bankruptcy,” each Fall since 2005
  • Northeastern University, M.A. Taxation Program, “State and Local Tax Planning,” 2005, 2006
  • Portland Community College, “Business Law,” 1996, 1997, 1998, 1999
  • Strafford Legal Webinars CLE/CPE Program, “Final FATCA Deadline Approaches: Compliance & Implementation,” October 2013
  • New England Archivists Annual Meeting, “Value Appraisals,” Fall 2009
  • Massachusetts Continuing Legal Education (MCLE): “A Practical Guide to Organizing a Business,” November 2008; “Tax Issues for the Business Attorney” September, 2008; “Tax Aspects of Mergers & Acquisitions,” November 2007

News & Insight


Qualified Opportunity Zones: Insights from the Government's New Guidance

November 21, 2018

Hinckley Allen published A Practical Guide to the Qualified Opportunity Zone Program, which details a promising new program contained in the 2017 Tax Cuts and Jobs Act that provides significant tax incentives for real estate investors in Qualified Opportun…


A Practical Guide to the Qualified Opportunity Zone Program

August 14, 2018

Among the many changes and incentives contained in the 2017 Tax Cuts and Jobs Act, one of the most promising is the Qualified Opportunity Zone (QOZ) program.[1] This program was created to encourage investment in distressed areas of the country. It aims to…


The Tax Cuts and Jobs Act: Implications for Tax-exempt Entities

July 12, 2018

The Tax Cuts and Jobs Act (TCJA) enacted at the end of 2017 had an immediate impact on all taxpayers, including tax-exempt entities. Nonprofits are faced with new excise taxes, changes to unrelated business taxes, and shifts in charitable giving incentives…


Real Estate & Tax Update: IRS Reverses Course on Partnership Tax Implications of Bad Boy Guarantees

April 22, 2016

Real estate investors will be relieved to know that the Internal Revenue Service (IRS) has reversed course on a controversial position.In our March client alert,[1] we reported that the IRS released Chief Counsel Advice (CCA) 201606027[2] on February 5,…


New Partnership Audit Procedures Create Uncertainty around Partnership Agreements

April 7, 2016

Every business in partnership form is affected by the recent signing[1] of the Bipartisan Budget Act of 2015 (the “Budget Act”) and should re-examine the tax provisions of its partnership agreements.Revenue Service (IRS) for all entities treated as …


IRS Advice on Bad Boy Guarantees Should Concern Real Estate Investors

March 28, 2016

The Internal Revenue Service (IRS) recently published advice that raises concerns for investors in real estate partnerships1. The published advice changes the tax implications for investing partners when a partnership’s real estate financing document inc…


Highway Funding Bill Brings Important Tax Changes

August 4, 2015

Among the important tax provisions of HR 3236 are the following.Certain US persons with foreign financial accounts are required to file FinCEN Form 114, Report of Foreign Bank and Financial Accounts (FBAR). The FBAR form originated under the Bank Secrecy A…


2014 Year-End Tax Planning for Businesses

December 4, 2014

As 2015 approaches, now is the time for businesses to assess their 2014 tax liabilities and take advantage of tax planning opportunities. This article is intended to inform you of important federal tax provisions to be aware of and federal tax planning str…


2014 Year-End Tax Planning for Individuals

December 4, 2014

As you get set to welcome 2015, now is the time to take steps toward managing your tax liability for 2014. Although you will not file your 2014 tax returns until 2015, many tax planning strategies need to be acted on prior to December 31, 2014. This articl…


2013 Developments in U.S. International Tax

April 11, 2014

U.S. international tax is a constantly evolving field, and this was certainly true in 2013.  This article highlights several of the developments during the past year.


Section 1202: Opportunity for Tax Savings upon the Sale of Small Business Stock

October 31, 2013

Small business owners often shun C Corporation status because of its various tax drawbacks, perhaps most significantly, the dreaded double tax.  However, in recent years, Congress has enacted tax provisions designed to incentivize new investment in small …


Planning for the Tax Hike

August 9, 2012

Anyone who owns, develops, or invests in real estate should note that dramatic changes in the tax landscape are likely, effective January 1, 2013. We cannot yet know the precise tax code changes, but we can predict that important windows of opportunity may…


No Good Deed Goes Unpunished? - Increased Responsibilities for Volunteer Board Members

May 15, 2012

For people who give their time and money to serve on non-profit boards, a recent ruling of the United States District Court should serve as a flashing yellow light. In Roy Don Bunch v. Commissioner of Revenue (No. 2:10-CV-122), the Court for the Eastern Di…


FIN 48 Creates Unexpected Risks in Business Sales

July 1, 2008

A Practical Approach to Avoiding the Golden Parachute Excise

March 1, 2007

Private Corporations and the New Golden Parachute Regulations

September 1, 2004

Voice Over IP: The Second Battle of the Internet Tax War

June 21, 2004

Offshore Migration of U.S. Intellectual Property: an Unintended Effect of Transfer Pricing Regulations

October 21, 2002
Show More Publications
Firm News

New Partner Joins Hinckley, Allen & Snyder’s Boston Office

March 9, 2012

BOSTON, MA: Hinckley, Allen & Snyder LLP announced that tax attorney Avi Lev has joined the firm as a partner in its Corporate and Business Law Group.Lev’s practice focuses on analyzing the tax impacts of various business transactions and representin…

Case Study

Hinckley Allen Represents Cynosure, Inc. in $287M Transaction

Hinckley Allen recently represented Cynosure, Inc. (NASDAQ: CYNO) in its acquisition of Palomar Medical Technologies, Inc. (formerly NASDAQ: PMTI), a leading researcher and developer of innovative aesthetic light-based systems for hair removal and other co…

Case Study

Hinckley Allen Represents Rockville Financial Inc. in $369 Million Transaction with United Financial Bancorp, Inc.

Hinckley Allen represented Rockville Financial Inc., and its subsidiary Rockville Bank in its historic merger of equals with United Financial Bancorp, Inc. and its subsidiary United Bank. Although the legal acquirer, Rockville adopted the United name. The …