Dan Small is a partner in Holland & Knight's Miami and Boston offices. He practices in the area of litigation, focusing on witness preparation, dispute strategies, government and internal investigations, white-collar criminal law and complex civil litigation. He has extensive investigation, jury trial and other litigation experience. Prior to entering private practice, Mr. Small was a prosecutor for the U.S. Department of Justice, during which time he tried RICO, corruption, financial and regulatory cases. Mr. Small received various awards and commendations for his work. He also was general counsel for a publicly traded healthcare management firm, where he oversaw in-house legal and risk management staff, outside counsel, litigation, compliance, and facility, entity and physician contracting.

Mr. Small has written several books on litigation for the American Bar Association, including Preparing Witnesses and Going To Trial, that are used in CLE programs he gives throughout the country. He was a Lecturer on Law at Harvard Law School. He is also a frequent television, radio and newspaper commentator, as well as the host of Holland & Knight’s Powerful Witness Prep Podcast Series.

Mr. Small has represented witnesses, plaintiffs and defendants in a wide range of internal and external investigations, administrative proceedings, and civil and criminal litigation. These have included issues relating to government regulation, healthcare entities, education institutions, financial institutions and others.

Representative Matters

  • Successfully defended former Virginia Governor Bob McDonnell during the investigation, trial and appeal. After the U.S. Supreme Court issued a unanimous decision vacating the convictions, the Department of Justice dismissed all charges against the Governor.
  • Representing private equity firm against clawback claims for fraudulent transfer on one of its investment redemptions
  • Counsel in a prominent SEC internet fraud case
  • Special Counsel to the Rhode Island Ethics Commission
  • Special Counsel to the Massachusetts House Ethics Committee
  • As General Counsel to a publicly traded healthcare management firm, oversaw in-house legal and risk management staff, outside counsel, PLI and other litigation, facility, entity and physician contracting
  • Outside General Counsel to a group of long term care companies
  • Lead defense counsel for former Louisiana Governor Edwin Edwards


  • Harvard Law School, J.D.
  • Harvard College, B.A., cum laude
Bar Admissions/Licenses
  • Florida
  • Massachusetts
  • Regional Dialogue Advisory Council, Slovenia and Uzbekistan
  • Litigation Counsel of America, Senior Fellow
  • American Bar Association, Criminal Justice Section and former Vice Chair, White Collar Crime Committee
  • The Florida Bar
  • Massachusetts Bar Association
  • Federal Bar Association
  • American Health Lawyers Association
Honors & Awards
  • The Best Lawyers in America, Criminal Defense: White-Collar, 2013-2024
  • Massachusetts Super Lawyers magazine, 2018-2020, 2022, 2023
  • Holland & Knight Pro Bono All-Star, 2020, 2021
  • Guide to the World's Leading White Collar Defense Lawyers, Legal Media Group's Expert Guides, 2015
  • Martindale-Hubbell AV Preeminent Peer Review Rated


Podcast - Basic Points to Consider in Redirect Examination 
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Berkeley Unified Superintendent Set to Testify Before U.S. House Education Panel
Trial Lawyers Handbook
Podcast - Direct Examination: Offering Exhibits
Podcast - Direct Examination: Looping and Bookending
Trial Lawyer's Handbook Ep. 33 Still
Podcast - Direct Examination: Getting Rid of Clutter
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Podcast - Direct Examination: Asking Questions in the Right Order
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Podcast - Direct Examination: Controlling a Friendly Witness
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Podcast - Direct Examination: To Lead or Not to Lead
Podcast - The Basic Elements of Direct Examination
Podcast - The Basic Elements of Direct Examination
Podcast - Opening Statements: Some Common Challenges
Podcast - Opening Statements: Common Mistakes
Trial Lawyers Handbook
Podcast - Opening Statements: The Prohibition Against Argument
Podcast - Opening Statements: Telling the Story
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Podcast - Openings of Openings
Podcast - The Basics of Opening Statements
Podcast - Effective Trial Language Part 3: Jargon
Podcast - Effective Trial Language Part 2: Legalese
Podcast - Effective Trial Language Part 2: Legalese
Ep. 20 - Effective Trial Language Part 1: Noise
Podcast - Effective Trial Language Part 1: Noise
Podcast - Dealing with Evidence of Time, Distance and Speed
Podcast - Why Demonstrative Aids Are Critical in Every Case
Podcast - Using Technology in the Courtroom
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Podcast - Showing Exhibits to the Jury
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Podcast - Exuding Credibility in the Courtroom
Podcast - Key Lessons and Takeaways for Jury Trials
Podcast - The Pitfalls of Technology in Trials
Podcast - The Importance of Civility in Trial Law
TLH Ep 11 Still
Podcast - Bringing Mindfulness and Best Practices to Trial Law
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Podcast - A Checklist of Common Objections
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Podcast - Basic Courtroom Etiquette
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Podcast - Position and Movement in the Courtroom
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Podcast - The Different Ways Lawyers Prepare Notes for Trial
Podcast - Understanding the Importance of Chronology
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Podcast - The Key to a Successful Trial Lawyer
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Podcast - The Five Most Common Faults of Trial Lawyers
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Podcast - The "Five P's" That Will Help Shape Jurors' Emotions
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Podcast - The Differences Between Persuasion and Argument


Speaking Engagements