McLane Middleton understands that taxes directly affect the bottom line of every business.

Our tax law department is knowledgeable and experienced in assisting clients on a variety of tax-related transactions and business and tax planning matters, including:

  • Corporations
  • Individuals
  • Small, closely held businesses
  • Multinational conglomerates
  • Shareholders
  • Tax Exempt Entities
  • Buyers and Sellers

Our tax law attorneys provide clients with creative and individually tailored solutions that are specially designed to help them achieve their business and financial objectives.  Our tax attorneys have the unique perspective of frequently participating in the drafting of New Hampshire’s tax legislation.

Federal Tax Planning

McLane Middleton tax attorneys advise clients on a broad range of federal tax planning issues, including:

  • Choice of Entity: We help clients select the form of entity that suits their needs, which could include: proprietorship, partnership, S corporation, C corporation, limited liability company, limited partnership, limited liability partnership, or trust.
  • Mergers & Acquisitions: Businesses expanding through mergers or acquisitions seek our representation for our knowledge of the tax impact on their transactions. These can include the allocation of basis among acquired assets, consideration of non-competes or consulting agreements, and assessing the form of the acquired entity.
  • Spin-offs, Liquidations & Restructuring: To help our clients avoid tax penalties to the corporation or shareholders, our attorneys assist with preserving net operating losses.
  • Sale or Divisions: Our attorneys help determine whether the transaction can or should be accomplished on a tax-free basis and, if not, whether assets or stock should be sold.
  • Termination of Business: McLane Middleton’s tax attorneys know our clients want to pay as little tax as possible, and we assist in providing an appropriate legal entity to receive the assets of the business upon termination or liquidation.
  • Tax Qualified Retirement Plans: We draft and advise clients on all types of retirement plans, including: 401(k), pension, profit sharing, and ESOPs.
  • Financing Transactions: We facilitate structured borrowings, venture capital, private placements and public offerings, and the review of loan documentation from a state and federal tax perspective.
  • Stock Options and Executive Compensation: McLane Middleton lawyers help employers implement and administer stock option and all other types of nonqualified deferred compensation plans.  We also help with worker classification determinations.
  • Real Estate Transactions: We aid in structuring like-kind exchanges, sale/leasebacks, real estate investment trusts, and conservation property easements.
  • Self-Directed IRAs: We assist clients in utilizing their IRAs for real estate investments and closely held businesses.
  • Tax Return Preparation and Review: Our tax department prepares federal and state tax returns for individuals and business trusts and estates, and is often asked to review returns to aid in minimizing taxes.

Retirement Plans and Employee Benefits

McLane Middleton provides a range of employee benefit advice to help clients select, implement, and administer employee benefit plans. Our attorneys are experts in:

  • 401(k), Defined Benefit, and Profit Sharing Plans: Our attorneys assists clients in selecting the plan that best fits their needs. We assist them to administer and maintain their plans in compliance with all tax qualification and ERISA required demands.
  • Plan Termination: McLane Middleton expertly advises our clients through the plan termination process whenever the plan’s continuation become too burdensome, the retirement plan is no longer cost-justified, or it otherwise becomes necessary to terminate the business.
  • Voluntary Correction Programs Submission: Our attorneys have substantial experience assisting clients to bring their plans back into agreement with the tax code and ERISA requirements, and when necessary, utilize the appropriate IRS or U.S. Department of Labor programs.
  • Benefit Plans and Corporate Transactions: Our attorneys advise clients buying and selling businesses on how the rules governing benefit plans will impact the transaction.
  • QDRO: McLane Middleton attorneys review Qualified Domestic Relations Orders (QDRO) to ensure they meet tax code, ERISA and court requirements, to ensure that the retirement plans are protected from future claims.
  • Health Insurance and Welfare Plans: McLane Middleton attorneys have substantial experience with the ACA and other laws and regulations impacting health insurance, disability insurance, and other employer-provided benefits.

Employee Stock Ownership Plans (ESOPs)

Our tax attorneys capably structure Employee Stock Ownership Plan (ESOP) transactions, particularly from the perspective of plan sponsors, fiduciaries, and selling equity holders, and draft documentation for all aspects of those transactions.

McLane Middleton’s lawyers advise our clients on structuring the ESOP and draft associated documents. We also assist shareholders with the tax-deferred rollover of sale proceeds.

Executive Compensation Planning

McLane Middleton’s Tax Group designs all types of nonqualified plans for corporate and tax exempt entities.  Common types of nonqualified plans include:

  • Stock option and restructure stock
  • Deferred compensation
  • Stock appreciation rights and phantom stock
  • Bonus plans
  • Supplemental executive retirement plans (SERPs)
  • Change of control plans
  • 457(b) and 457(f) plans

Our attorneys regularly review executive employment agreements in transactions to avoid unnecessary tax liability for golden parachutes, deferred compensation, and other executive arrangements.  We also regularly advise clients in navigating the complex rules of Tax Code Section 409A that governs deferred compensation.  McLane Middleton attorneys stay current on fast-breaking issues and are frequent speakers on executive compensation developments.

State & Local Tax Planning

Our attorneys regularly represent clients confronting state and local tax issues, including:

  • State and Local Tax Audits: We represent clients before various tax agencies, and have been effective in minimizing taxes, penalties, and interest assessed.
  • Tax Litigation: Our attorneys have a history of success in representing clients before the U.S. Tax Court, New Hampshire Department of Revenue Administration, Massachusetts Department of Revenue, and Superior Courts.
  • Reasonable Compensation: McLane Middleton’s tax group has provided skilled representation of a variety of small business owners under audit by the State of New Hampshire for "reasonable compensation" issues.
  • Rulemaking and Legislation: Through lobbying activities, involvement in working groups, and working with clients, we assist in improving state tax laws and in the review and streamlining of state agency practices and procedures.
  • Real Estate Tax Appeals: We have a history of successful client appeals before the New Hampshire Superior Court and Board of Tax & Land Appeals.

Tax Controversy

McLane Middleton's tax law expertise includes representing clients involved in various federal and state tax controversies:

  • Tax Audits & Criminal Investigations: Our skilled attorneys represent businesses and individuals during audit, appeal, or in court to obtain the best possible resolution of matters with the Internal Revenue Service (IRS), New Hampshire Department of Revenue Administration, Massachusetts Department of Revenue, and other taxing authorities.
  • Tax Litigation: McLane Middleton maintains a successful track record in pursuing tax issues before the U.S. Tax Court, New Hampshire Department of Revenue Administration, Massachusetts Department of Revenue, and Superior Courts on behalf of our clients.
  • IRS Collections: We have extensive experience obtaining resolution of our clients’ tax problems through the use of Offers in Compromise and Installment Agreements.

Tax-Exempt Entities

McLane Middleton’s tax attorneys comprehensively guide our clients in forming and maintaining tax-exempt entities. We routinely assist our clients with:

  • Formation: Organizing and filing the documentation necessary to establish tax-exempt entities.
  • IRS Exemption Submissions: Preparing and filing necessary documentation to obtain tax-exempt status from the Internal Revenue Service.
  • Planning: Avoiding or minimizing the effects of private foundation status, minimizing unrelated business income tax, and helping with internal audits.
  • Audits: Advocating at both the state and federal level when authorities raise questions regarding tax-exempt status, assert unrelated business income, or seek to impose private foundation penalties
  • Charitable Giving: Structuring a program of charitable giving to ensure the organization retains philanthropic status, and provides donors with appropriate deductions/documentation
  • Governance: We help boards comply with state and federal requirements for proper oversight of tax-exempt organizations and help them manage risks inherent with service as trustees and directors.

International Tax Planning

McLane Middleton is accomplished in helping U.S. and non-U.S. clients conduct their international business operations. Our attorneys regularly advise companies on the following complex international tax issues:

  • Choosing the correct business entity and restructuring foreign operations to minimize U.S. and foreign taxation
  • Planning for and determining the correct source of business and non-business income
  • Minimizing taxation through proper employee compensation structures
  • Working with foreign tax systems
  • Understanding the impact of U.S. tax treaties
  • Maximizing allowable foreign tax credits
  • Intercompany (transfer) pricing matters
  • Foreign currency affairs
  • U.S. controlled foreign corporations (CFC) and passive foreign investment company (PFIC) regimes.

Our history of success includes the structuring of a sale between a U.S. business with foreign subsidiaries in Germany and the Netherlands. This case handles repatriation of foreign source income, foreign tax credit allocation, the applicability of various tax treaties, Netherlands real estate transfer taxes, withholding rules for corporate dividends, and several pension concerns.

McLane Middleton is a member of Terralex, a worldwide network of independent law firms helping domestic and foreign clients to do business globally. Our attorneys are frequently asked to provide tax guidance to clients of other member firms.

Integrity and trust

At McLane Middleton we establish and maintain long-standing relationships with our clients to help us better achieve their unique goals over time. This approach to building trust requires that our esteemed lawyers and professionals use their broad, in-depth knowledge and work together with integrity to ascertain sound resolutions to legal matters for their clients.

Strength in numbers

McLane Middleton is made up of more than 105 attorneys who represent a broad range of clients throughout the region, delivering customized solutions. As a firm we are recognized as having the highest legal ability rating. The firm is rated Preeminent by Martindale Hubbell and is recognized as one of the nation's leading law firms in Chambers USA. Our attorneys are distinguished leaders in their respective practice areas.

Meet Our People

Commitment and collaboration

McLane Middleton's versatile group of attorneys and paralegals become trusted authorities on each case through collaboration. We work with our clients to learn their individual needs first and foremost and, together, we develop comprehensive solutions to their specific legal matters. This approach helps us exceed our clients' expectations efficiently and effectively, client by client, case by case.

Practice Areas

A history of excellence

McLane Middleton was established in 1919 in New Hampshire, and has five offices across two states. However, deep historical roots don't allow you to become innate. Our firm is organized, technological, and knowledgeable. Our history means we are recognized. But our reputation is built on the highest quality of service and experience in very specific areas of law.

The Firm

Intelligence paired with action

Our team continuously seeks opportunities to enhance their professional development and put key learnings to action. The pursuit of further insight guides us to volunteer service opportunities, speaking engagements, and teaching roles. Our lawyers are sought after thought leaders across their industries, and recipients of leadership awards throughout the region.