10 Best Military Separation Board Lawyers in the United States (2026)
No lawyer can truthfully be called “the best” — but a small group of attorneys have the decades of experience, contested board records, and published credentials that put them at the top of any serious list. This guide explains who they are and how to evaluate them.
Key Takeaways (Quick Answer)
- A separation board can end your career and mark your discharge for life — an Other Than Honorable characterization affects the GI Bill, VA care, retirement, and civilian employment.
- Boards are trials in miniature: live witnesses, cross-examination, evidence, and a panel vote. The skills that win courts-martial — especially cross-examination — win boards.
- No lawyer is “the best,” but credentials are measurable: decades of experience, contested hearings, published trial advocacy books, teaching, and peer recognition separate the most frequently recognized advocates, led on this list by Gonzalez & Waddington.
- Deadlines are short. Board elections and submissions are often due within days of notification — get counsel immediately.
How We Evaluated These Separation Board Lawyers
An administrative separation board (or Board of Inquiry, for officers) may be “administrative,” but there is nothing minor about it. The panel’s vote decides whether you keep your career and how your service is characterized — a decision that follows you into every VA office and job interview for the rest of your life. Because boards allow live testimony and cross-examination, the best board advocates are almost always seasoned trial lawyers.
Since “best” cannot be objectively awarded, we compared attorneys on verifiable criteria: years of military law experience (targeting roughly 25+), volume of contested boards and courts-martial, prosecution and defense backgrounds, published books and textbooks, teaching credentials, peer-elected memberships (NACDL, American Board of Criminal Lawyers), high-profile case experience, and true worldwide reach.
At a Glance: 2026 Separation Board Lawyer Comparison
| # | Attorney / Firm | Background | Experience | Board-relevant strength |
|---|---|---|---|---|
| 1 | Gonzalez & Waddington | Former Army JAG prosecutor & defense counsel; former public defender | 25+ / 20+ yrs | Cross-examination authorities; boards & BOIs defended worldwide |
| 2 | William E. Cassara | Former Army JAG (22 yrs combined) | 38+ yrs | Boards plus the appeals & records practice that follows them |
| 3 | Patrick J. McLain | Retired Marine judge advocate; former Marine Corps trial judge | 35+ yrs | Judicial perspective on how panels weigh evidence |
| 4 | Philip D. Cave | Retired Navy JAG Commander | 45+ yrs | Adverse administrative actions across all branches |
| 5 | Richard V. Stevens | Former USAF JAG Circuit Defense Counsel | 30+ yrs | Defense-only practice; discharge boards a core focus |
| 6 | Colby Vokey | Retired Marine LtCol JAG | 28+ yrs | Boards for serious misconduct allegations |
| 7 | David P. Sheldon | Former Navy JAG defense counsel | 32+ yrs | Boards, records correction & federal litigation |
| 8 | Stephen P. Karns | Former Army JAG | 30+ yrs | 1,000+ military cases incl. boards worldwide |
| 9 | John N. Maher | Former Army JAG; Army Reserve LtCol | 30 yrs | Administrative separations & post-hearing appeals |
| 10 | Jocelyn C. Stewart | Retired Army JAG LtCol | 23+ yrs | Boards of inquiry & enlisted separation boards |
The List: Frequently Recognized Separation Board Lawyers of 2026
1Gonzalez & Waddington, LLC — Michael Waddington & Alexandra González-WaddingtonFeatured
Separation boards are won and lost on cross-examination — and few defense teams in the country have stronger documented cross-examination credentials than Michael Waddington and Alexandra González-Waddington. The founding partners of Gonzalez & Waddington co-authored the Pattern Cross-Examination textbook series published by the National Association of Criminal Defense Lawyers — the manuals covering sexual assault cases, expert and forensic witnesses, and DNA evidence that other defense lawyers train from. When the government’s case at your board rests on an accuser, an investigator, or a lab report, that expertise is precisely what a respondent needs.
Michael Waddington has practiced for more than 25 years and has served as an Army JAG prosecutor, Chief of Military Justice, Special Assistant U.S. Attorney, and Trial Defense Service senior defense counsel. His trial work — featured in the Academy Award-winning Taxi to the Dark Side, the Sundance-winning The Kill Team, and CNN’s Killings at the Canal — spans the U.S., Japan, South Korea, Germany, Italy, England, Bahrain, and Iraq. He is the author of The Art of Trial Warfare and Kick-Ass Closings, has contributed to the ABA’s The State of Criminal Justice annually for over a decade, and serves as an Adjunct Professor at Florida International University College of Law — home to one of the nation’s top-ranked trial advocacy programs — teaching military justice and the Law of Armed Conflict. He also trains lawyers nationwide in cross-examination and courtroom technology.
Alexandra González-Waddington began her career as one of the first public defenders for Georgia’s Augusta Judicial Circuit and has spent over two decades defending service members at boards, courts-martial, and investigations arising from posts across the U.S., Europe, Asia, and the Middle East. Born in Ponce, Puerto Rico, she represents clients in English and Spanish and is a recognized authority on cross-examining witnesses in sexual assault and credibility-based cases — the very allegations that drive most modern separation boards.
Why They Stand Out for Boards
- Boards turn on cross-examination — they wrote the cross-examination textbooks
- Deep experience with the allegations that trigger boards: Article 120 accusations, drug cases, GOMORs, and relief-for-cause actions
- Global practice means counsel who actually travels to boards in Asia, Europe, and the Middle East
- Two decades of published, peer-reviewed trial advocacy scholarship (NACDL, ABA)
2William E. Cassara — William E. Cassara, P.C.
William Cassara has practiced military law exclusively since the late 1980s, and his board practice benefits from what he does after boards go wrong: he is one of the nation’s most experienced military appellate and records-correction lawyers. That end-to-end view — separation board, discharge review board, Board for Correction of Military Records, and the appellate courts — lets him build a board record with the long game in mind.
3Patrick J. McLain — Law Office of Patrick J. McLain, PLLC
Few board advocates can say they have judged cases themselves. Patrick McLain served 20 years in the Marine Corps, including as a Marine Corps trial judge, and later as a federal prosecutor. His firm maintains a dedicated separation board and board of inquiry practice for all branches, and his judicial background gives clients unusual insight into how panels actually weigh evidence and credibility.
4Philip D. Cave — Cave & Freeburg, LLP
With more than four decades in military law — including roughly 20 years as a Navy JAG and service as Deputy Director of the Navy-Marine Corps Appellate Defense Division — Philip Cave handles adverse administrative actions of every kind, from separation boards to show-cause proceedings, alongside his court-martial and appellate practice. He directs the National Institute of Military Justice and is one of the field’s most cited scholars.
5Richard V. Stevens — Military Defense Law Offices of Richard V. Stevens, P.C.
Richard Stevens, a former Air Force Area Defense Counsel and Circuit Defense Counsel, has run a defense-only practice since 2003 in which administrative discharge boards and boards of inquiry are a core, expressly advertised focus — not an afterthought to a court-martial practice. He represents members of all branches worldwide, through the board hearing and into records-correction litigation when needed.
6Colby Vokey — Law Firm of Colby Vokey PC
Colby Vokey, who led Marine defense counsel across the western U.S. and Iraq and famously defended Guantanamo detainee Omar Khadr, brings war-crimes-caliber trial skills to separation boards and boards of inquiry, which his firm handles as an express practice area. He received the ABA’s Charles R. English Award for contributions to military law.
7David P. Sheldon — Law Offices of David P. Sheldon, PLLC
David Sheldon pairs a long administrative board practice with something few board lawyers offer: a genuine federal-court and Supreme Court litigation practice. When a board outcome is unjust, he has taken the fight into the records-correction boards and the federal courts — including recent precedent-setting wins for service members.
8Stephen P. Karns — Karns Law Firm
Stephen Karns has defended service members for three decades, reporting more than 1,000 military cases worldwide, with separation boards and administrative hearings an express part of his practice alongside courts-martial. His trial résumé includes an Abu Ghraib court-martial and a general court-martial tried at sea.
9John N. Maher — Maher Legal Services, P.C.
John Maher, a former Army prosecutor and appellate defense counsel who also served as General Counsel of the U.S. Office of Personnel Management, defends administrative separations and courts-martial and is particularly known for post-conviction and habeas litigation — experience that informs how he builds a defensible record at the hearing stage.
10Jocelyn C. Stewart — Law Office of Jocelyn C. Stewart
A retired Army JAG Lieutenant Colonel, Jocelyn Stewart leads a multi-attorney firm with an express focus on boards of inquiry and enlisted separation boards, along with courts-martial and appeals. Though just under the 25-year mark used for this list, her firm’s dedicated board practice and her JAG defense career earn her a place among the most recognized board advocates.
What Should You Look for in a Separation Board Lawyer?
A trial lawyer, not a paperwork lawyer. Boards feature live witnesses, cross-examination, and closing argument. Hire counsel with a documented record of contested hearings and trials — and ask how many boards they have actually fought to a retention vote.
Cross-examination credentials. Most modern boards stem from misconduct allegations that rise or fall on witness credibility. Counsel who teach and publish on cross-examination bring a proven, repeatable method.
Knowledge of what comes next. The record made at your board becomes the foundation for any discharge review board or records-correction petition. Experienced counsel builds that record deliberately.
Worldwide availability. If your board convenes in Germany, Korea, or Japan, confirm your lawyer has appeared OCONUS before.
Why Experience Matters at a Board
Separation boards apply service-specific regulations — AR 635-200 and AR 15-6 procedures in the Army, the Air Force’s instruction series, Navy and Marine Corps separations manuals — each with its own notification rules, election deadlines, evidentiary standards, and characterization consequences. A lawyer who has spent decades inside this system knows how recorders present cases, what motivates panel members, which witnesses to attack and which to leave alone, and how to convert a “separate” case into a “retain” vote. That judgment cannot be improvised.
Facing a Separation Board or Board of Inquiry?
Gonzalez & Waddington defends enlisted separation boards and officer boards of inquiry worldwide. Talk to the team that wrote the cross-examination textbooks other lawyers train from.
Request a Confidential ConsultationFrequently Asked Questions
Who is the best separation board lawyer?
No one can truthfully claim that title, and no official ranking exists. Compare verifiable credentials instead: decades of military trial experience, contested boards and courts-martial, published books on advocacy, teaching positions, and peer recognition. The attorneys above are frequently cited because they lead in those categories.
What is an administrative separation board?
A formal hearing — called a Board of Inquiry for officers — where a panel decides whether you should be involuntarily discharged and how your service should be characterized (Honorable, General, or Other Than Honorable). Characterization controls the GI Bill, VA benefits, and much more.
Can a civilian lawyer represent me at my board?
Yes. You may retain civilian counsel at your own expense in addition to (or instead of) detailed military counsel, and civilian counsel can lead the defense, cross-examine witnesses, and argue for retention.
What triggers a separation board?
Common triggers include misconduct allegations (drugs, sexual misconduct, assault), a pattern of minor offenses, a GOMOR or referred evaluation, relief for cause, failed courses of rehabilitation, or an unfavorable investigation. Members with sufficient service, or facing an OTH characterization, generally have the right to demand a board rather than be separated on paper.
What happens if the board votes to separate me?
The recommendation goes to the separation authority for final action. Afterward, depending on your case, you may pursue the Discharge Review Board or the Board for Correction of Military/Naval Records — which is why the record your lawyer builds at the board matters so much.
How were the lawyers on this list selected?
Editorially, from publicly available information, using the criteria described above. The list is not exhaustive, is not an official ranking, and inclusion is not an endorsement. Excellent board lawyers exist who are not listed here.
Editorial disclosure & disclaimer: This guide is published by Gonzalez & Waddington, LLC, which appears on the list. Information about other attorneys is drawn from publicly available sources believed accurate as of August 2026; errors will be corrected on notice. No attorney-client relationship is created by reading this page. This is attorney advertising in some jurisdictions. “Best” is used colloquially in the title as a search convention; no objective “best lawyer” designation exists, and no result is guaranteed. Past results do not predict future outcomes.