"His strengths include the ability to speak about the law in layman's terms, strong follow-through, and an unbelievable attention to detail"  - Chambers USA

"a great litigator, a good strategic thinker and an excellent advocate"   - Chambers USA

Mr. Ruchelman is a Member in Caplin & Drysdale's Washington, D.C., office, where he concentrates his practice in tax litigation and controversies with the Internal Revenue Service and other tax authorities. He also represents clients in general tax matters.


Mr. Ruchelman has extensive experience in resolving tax matters at all stages of tax disputes including IRS examinations, IRS appeals, post-appeals mediation, trial court litigation, and appellate litigation. He has litigated cases in the U.S. Tax Court, various U.S. district courts, and the U.S. Court of Federal Claims.

Building on his experience with the TEFRA partnership provisions, Mr. Ruchelman has spent a significant amount of time studying, speaking on, and writing about the new IRS tax and collection procedures relating to partnerships and limited liability companies that were recently enacted under the Bipartisan Budget Act of 2015. Since enactment of the new statute, Mr. Ruchelman has spoken on panels with a Tax Court judge, government officials from the Treasury Department and IRS Office of Chief Counsel, as well as other practitioners before the American Bar Association, American Institute of CPAs, DC Bar Association, and Bloomberg/BNA.

Mr. Ruchelman is an active member of the firm’s Complex Litigation group.  While at the Department of Justice, he participated in two separate two-month long trials with extensive pre-trial discovery in U.S. district court.  In private practice, Mr. Ruchelman regularly takes and defends depositions, engages in formal discovery including managing large document reviews, and engages in extensive motions practice.

Highlights & Representative Matters

  • Representing captive insurance managers in responses to Section 6112 list requests from the IRS.
  • Representing dozens of companies in all stages of Internal Revenue Service examinations involving captive insurance arrangements.
  • Representing clients before the U.S. Senate Finance Committee with respect to its investigation of syndicated conservation easement transactions.
  • Achieved a successful resolution before the IRS Office of Appeals involving a trust income tax case involving approximately $200 million.
  • Represented numerous clients in all stages of Internal Revenue Service examinations and Government investigations involving foreign accounts and foreign entities.
  • Reached global settlement with IRS Office of Chief Counsel in 80 separate Tax Court cases involving common employee benefit plan tax issues.
  • Represented third-party witness in Amazon.com Inc. & Subsidiaries transfer pricing case before the U.S. Tax Court.
  • Represented a large Wall Street financial services firm in appeal to the 7th Circuit Court of Appeals (JPMorgan Chase & Co. v. C.I.R., 530 F.3d 634 (7th Cir. 2008)).
  • Represented a hedge fund and its tax matters partner in a three-way IRS examination that led to litigation with the IRS and an adverse partner in the U.S. Court of Federal Claims (Imprimis Investors LLC v. United States, 83 Fed. CI. 46 (2008)).
  • Successfully defended Hawaii Department of Taxation and its employees against unlawful disclosure claims in the U.S. District Court (Marsoun v. United States, 525 F. Supp.2d 206 (D. D.C. 2007)).
  • Represented an international accounting firm in litigation concerning privilege issues (United States v. BDO Seidman LLP, 2004 WL 1470034 (N.D. Ill, June 28, 2004)).
  • Represented a tax attorney in proceedings brought by the IRS Office of Professional Responsibility in the U.S. administrative court. IRS conceded significant issues on the eve of trial.
  • Achieved a favorable settlement for a high-net-worth family in an IRS examination involving family limited partnership issues.
  • Attained a favorable settlement for a high-net-worth individual in an IRS examination involving a contribution of a conservation easement.
  • Successfully resolved an examination involving promoter penalty issues in IRS post-appeals mediation.
  • Obtained a complete abatement and refund of over $600,000 of late filing, late payment, and late deposit penalties for multiple years for an oil services company relating to cross-border leasing payments and Form 1042.

  • Successfully resolved expatriation case, reducing over $2,000,000 in proposed tax and over $400,000 of penalties to less than $75,000 in tax and no penalties.

Other Representative Matters

Mr. Ruchelman has represented clients before the IRS examination division, IRS Appeals, or in court involving the following substantive tax issues: IRS collections, family limited partnerships, contributions of conservation easements; estate and gift taxes, oil and gas partnerships, residency issues, restricted interest, employee benefits, and tax shelter disclosures. He also has considerable experience responding to IRS third-party summonses.

Admissions & Education

Bar & Court Admissions
  • District of Columbia
  • Maryland
  • New York
  • U.S. Tax Court
  • U.S. District Court, District of Columbia
  • U.S. District Court, Southern District of New York
  • U.S. Court of Federal Claims
  • U.S. Court of Appeals, Federal Circuit
  • U.S. Court of Appeals, D.C. Court
  • U.S. Court of Appeals, Seventh Circuit
  • U.S. Bankruptcy Court, District of Columbia  

LL.M. in Taxation, Georgetown University Law Center, 1999

J.D., Syracuse University College of Law, 1993, cum laude

B.S., George Mason University, 1990, with distinction

Recognitions & Noteworthy

Honors & Recognitions
  • Chambers USA, 2016-Present
  • The Legal 500, Leading Lawyer, 2011, 2012; Recommended, 2014, 2019-Present
  • Best Lawyers in America, 2021-Present
  • Super Lawyers, Washington, D.C., 2013-Present
  • The Washington Post, Top Attorneys in D.C., 2014

Government Service

Before joining Caplin & Drysdale, Mr. Ruchelman was a Trial Attorney with the U.S. Department of Justice, Tax Division, and an Attorney with the Internal Revenue Service, Office of Chief Counsel.

While at the Department of Justice, he litigated tax cases in the federal district courts and the U.S. Court of Federal Claims. For his work representing the government in extended trials involving the IRS's attack on leveraged corporate-owned life insurance as a tax shelter, Mr. Ruchelman received the Attorney General's Distinguished Service Award.

Professional Activities & Affiliations

Professional Activities

Mr. Ruchelman recently completed his tenure as Chairman of the Tax Audits and Litigation Committee for the Tax Section of the D.C. Bar. This committee presented monthly panel discussions on hot topics in the tax audits and litigation arena and frequently interacted with IRS and DOJ tax officials. He is also an active member of the American Bar Association Section of Taxation, the Court of Federal Claims Bar Association, and the U.S. Tax Court's J. Edgar Murdoch Inns of Court.

Other Professional Affiliations

Past Chair, District of Columbia Bar, Section onTaxation, Tax Audits and Litigation Committee

Member, American Bar Association, Section of Taxation

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