Peter D. Randolph

"Our clients' lives don't stop at the state line; I take pride in advising clients comprehensively on issues that affect their lives and livelihoods across the entire region."


Peter Randolph is a Principal in Miller, Miller & Canby’s Business and Tax practice group. His multijurisdictional practice is focused on taxation, business, and probate and trust administration.

With nearly two decades of comprehensive experience, Peter provides in-depth knowledge and expertise to craft effective strategies tailored to each client’s individual needs. He takes particular pride in spotting risks his clients had not previously seen and in crafting solutions to mitigate those risks and advance client interests.

Peter advises small businesses on partnership and corporate taxation, corporate governance, buy-sell agreements, reclassification, restructuring and succession planning. He advises entrepreneurs and startups on business and taxation issues, including choice of entity, Qualified Small Business Stock, funding through equity and non-equity participation of investors, and compliance.  He also acts as outside general counsel to a number of businesses.

Peter regularly advises executors, trustees and beneficiaries in the areas of probate and trust administration, including pre and post-mortem planning, and estate, gift, and fiduciary income tax. He works with high net worth individuals and families, producing comprehensive estate plans to maximize the client’s family, business, and financial security.

Prior to joining Miller, Miller & Canby, Peter was a Managing Member at Lawless, Randolph & Dale, LLC., having started as an associate before moving to partner and subsequently managing member of the firm.

Peter is active in leadership roles with legal organizations, including serving as a Fellow in the American College of Tax Counsel, Vice Chair of the ABA Taxation Section’s Closely Held Business Committee, and Council Member of the MSBA Tax Section. He has volunteered his time in the legal community, including serving as a Pro Bono Attorney with the Montgomery County Bar Association Pro Bono Clinic, and participating in the DC Bar Pro Bono Assistance Program and Bankruptcy Clinic.

A native New Yorker, Peter resides in Montgomery County with his wife and children.

Bar Admissions

  • Maryland
  • District of Columbia
  • Virginia
  • New York
  • Pennsylvania
  • California
  • United States District Court for the District of Maryland
  • United States District Court for the District of Columbia
  • United States Tax Court


Professional Affiliations

  • American College of Tax Counsel, Fellow 2024-Present
  • American Bar Association, Member, 2012-Present
    – Section of Taxation, 2013-Present;
    Vice Chair, Closely Held Business Committee, 2021-Present
    – Section of Real Property, Estates & Trusts, 2012-Present
    – Business Law Section, 2016-Present
  • Maryland State Bar Association, Member, 2009-Present
    – Taxation Section, 2014-Present; Tax Council, 2023-Present
    – Estates & Trusts Section, 2009-Present
  • Montgomery County Bar Association, Member, 2009-Present
    – Estates & Trusts Section, 2009-Present
    – Law Firm Management Section, 2016-Present
  • Montgomery County Bar Association Pro Bono Clinic, Pro Bono Attorney, 2010-2012
  • DC Bar Pro Bono Assistance Program, 2010-2014
  • DC Bar Pro Bono Bankruptcy Clinic, 2010-2013 


  • New York University School of Law, New York, NY
    LLM in Taxation, Executive Program, May 2023
  • American University Washington College of Law, Washington, DC J.D., May 2007
  • University of California, Santa Barbara, Goleta, CA B.A., History, June 2003

Honors and Awards

  • Fellow, American College of Tax Counsel

Speaking Engagements

  • Maryland State Bar Association Legal Summit (Upcoming); MSBA Tax Section/Trusts & Estates Section, Ocean City, MD; June 7, 2024.
  • ABA Section of Taxation 2024 Annual Meeting (Upcoming); Hot Topics for Closely Held Businesses, Closely Held Business Committee; Washington, DC; May __, 2024.
  • ABA Section of Taxation 2024 Midyear Tax Meeting
Hot Topics for Closely Held Businesses,
Closely Held Business Committee; San Francisco, CA; January 19, 2024
  • ABA Section of Taxation 2023 Fall Tax Meeting,
Planning for the Future: The Impact of Sunsetting TCJA Provisions Closely Held Business Committee; Virtual; October 19, 2023
  • Maryland State Bar Association Legal Summit,
Sports Betting – Are You Playing Tax Liability Roulette? MSBA Tax Council; Ocean City, MD; June 8, 2023
  • Maryland State Bar Association Legal Summit,
Irrevocable Trusts and Income Tax Considerations,
MSBA Estates & Trusts Council; Tax Council; Ocean City, MD; June 8, 2023
  • ABA Section of Taxation Annual Meeting,
Equity Incentive Compensation for Closely Held Businesses, Closely Held Business Committee; Washington, DC; May 5, 2023
  • Rossdale CLE,
High Net Worth Tax Mitigation and Tax & Estate Planning Teleconference; February 23, 2023; November 29, 2023
  • ABA Section of Taxation 2023 Midyear Tax Meeting,
Hot Topics for Closely Held Businesses,
Closely Held Business Committee; San Diego, CA; February 10, 2023
  • ABA Section of Taxation 2022 Fall Tax Meeting,
Practical Advice for Business Divorces Involving Interest Holders Treated as Employees for Non-Tax Purposes,
Closely Held Business Committee; Dallas, TX; October 14, 2022
  • ABA Section of Taxation Annual Meeting,
Cleaning Up Clients’ Past Behavior,
Closely Held Business Committee; Washington, DC; June 18, 2020
  • ABA Section of Taxation and Real Property Trusts & Estates Section, 2019 Joint Fall CLE, Navigating the River Styx, Come Sail Away with These Post-Death Elections,
Young Lawyers Forum; San Francisco, CA; October 4, 2019



Representative Tax Matters

  • Acted as Administrator of an insolvent estate and worked with theft victims, the Department of 
the Treasury, the U.S. Attorney’s office, and the IRS, to make distributions where Decedent failed to file income tax returns for over 20 years and had theft income in excess of $13 million during a portion of that time period. Included Federal Priority Act and Federal Priority Lien Act issues litigated against the IRS, resulting in favorable judicial opinion.
  • Advising personal representative and trustee in matter involving post-mortem planning resulting in elimination of multi-million dollar tax liability related to ownership and sale of real property in decedent’s solely owned S Corporation.
  • Advising personal representative in matter involving abatement of excise tax penalties due to failure to take required minimum distributions where no one was aware of the qualified retirement plan for almost a decade after decedent’s death.
  • Advising on sale of minority interest of multi-jurisdiction restaurant group, necessitating restructuring of entity for corporate and tax purposes.
  • Advised successor trustee on matters related to probate, trust administration, creditor claims, and tax issues, including preparation of amended prior-year individual income tax returns to secure refunds for estate based on theft losses where several million dollars was stolen by trusted advisor who died before resolution of the matter.
  • Advised on and prepared all necessary documents for structuring the redemption of membership interests in a financial services firm to achieve the best tax result under partnership tax rules.
  • Successfully appealed estate tax assessment to eliminate all estate tax liability where decedent, a non-lawyer, drafted his own inter-vivos trust, creating a situation where his surviving spouse with advanced dementia would have owed over $100,000 in state estate tax.
  • Leveraged an opportunity for tax savings through use of both parents’ estates, eliminating estate tax liability in full where parents died within several months of each other.
  • Successfully negotiated with the IRS to secure an installment agreement that saved client’s home from tax sale, in a case where income tax returns were not filed, nor tax liability paid over many years. Advised on best practices to maintain compliance moving forward.
  • Advised on restructuring business for transition of founder’s retirement which included the navigation of multiple partnership tax issues that otherwise would have created unknown liability to business and the remaining partners.


Practitioner (and Commissioner) Beware: Do Not Make the Palmarini Lack of Substantiation Mistake, ABA Tax Times, Vol. 42, No. 2, Winter 2023