Practice Areas
Tax Controversies Tax Litigation
Blogs / Additional Resources
Partnership Representative Captive Insurance
Education
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
Bar and Court Admissions
New York
District of Columbia 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
Charles M. Ruchelman
Member, Washington, D.C.(202) 862-7834 [email protected] "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.
Services
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.
Highlights
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.
Circuit
U.S. Bankruptcy Court, District of Columbia
Other Professional Affiliations
Past Chair, District of Columbia Bar, Section onTaxation, Tax Audits and Litigation Committee Member, American Bar Association, Section of Taxation
Government Experience
Attorney, U.S. Department of Justice, Tax Division, 1996-2003 Attorney, Internal Revenue Service, Office of Chief Counsel, 1993-1996
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.
Government Experience
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
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.
Awards & Rankings
Chambers USA, 2016-Present
The Legal 500, Leading Lawyer, 2011, 2012; Recommended, 2014, 2019-Present
The Legal 500, Top-Tier Firm, Tax - US Taxes - Contentious, 2010, 2015-Present
Best Lawyers in America, 2021
Super Lawyers, Washington, D.C., 2013-Present The Washington Post, Top Attorneys in D.C., 2014
Recent News
Chambers USA Recognizes Caplin & Drysdale Attorneys, May 20, 2021 Super Lawyers® Names Caplin & Drysdale Attorneys Among D.C.'s Most
Prominent Practitioners, Super Lawyers, April 29, 2021
Accounting Today Quotes Charles Ruchelman on CIC Services v. IRS, Accounting Today, January 27, 2021
Charles Ruchelman Talks to Bloomberg on CIC Services v. IRS, Bloomberg Law, December 30, 2020
Caplin & Drysdale Earns Top Ranking in 2021 "Best Lawyers in America", U.S. News & World Report, August 20, 2020
17 Caplin & Drysdale Attorneys Recognized in 2020 Legal 500 Ranking, The Legal 500, July 6, 2020
Chambers USA Recognizes Caplin & Drysdale Attorneys, May 5, 2020 Caplin & Drysdale D.C. Attorneys are Recognized by Super Lawyers®,
Super Lawyers, May 4, 2020
Charles Ruchelman Comments in Bloomberg on Taxpayer Privacy, Bloomberg Law, April 3, 2020
Charles Ruchelman Comments on Recent IRS Settlement Offer for Microcaptive Insurers in Tax Notes, Tax Notes, September 17, 2019 Click here for a full list of media coverage.
Recent Speaking Engagements
Panelist, Captive Legal and Tax Insights, Kentucky Captive Association, 2017 Kentucky Captive Association Educational Conference, June 16, 2017
Panelist, TOIs, Investigations, and Campaigns – the Tools of the IRS, Delaware Captive Insurance Association Spring Forum, May 8, 2017 Panelist, Part 5 of 6 Pass-Throughs and Real Estate and Part 6 of 7 Tax
Audits and Litigation Tax Series: Exploring the Proposed BBA Partnership Audit Regulations, D.C. Bar, April 5, 2017
Speaker, Captive Insurance: New IRS Tax Reporting Regime, AICPA, December 19, 2016
Speaker, Captive Insurance: New IRS Tax Reporting Regime Potential for Penalties and Examinations, Bloomberg BNA, December 9, 2016
Speaker, Small Captive Insurers and the New IRS Reporting Regime, Delaware Captive Insurance Association, December 1, 2016
Moderator, Fundamental Partnership Audit Reform, Part 2 - What's a Practitioner to Do?, District of Columbia Bar, Taxation Section, June 23, 2016
Speaker, New Tax Laws Relating to IRS Examination of and Tax Collection from Partnerships, American Institute of CPAs, May 16, 2016 Moderator, Litigating Partnership Tax Cases Under the New Partnership
Tax Rules of the Bipartisan Budget Act of 2015, American Bar Association Section of Taxation, May 6, 2016
Collection from Partnerships: Understanding the Nuances of the New Legislation, Bloomberg BNA, April 21, 2016
Click here for a full list of speaking engagements.
Recent Publications
"BLOG: IRS Releases Memo Concerning Access to Administrative File in TEFRA and BBA Examinations", with Lauren G. Smith,
www.PartnershipRepresentative.com, April 20, 2021
"BLOG: IRS Provides Penalty Relief for New Capital Reporting Requirements", with Lauren G. Smith,
www.PartnershipRepresentative.com, January 26, 2021
"Are The IRS's New Terms Worth It", with Benjamin Z. Eisenstat, Captive Review, December 22, 2020
"BLOG: IRS Releases Proposed Regulations on Centralized Partnership Audit Regime", with Lauren G. Smith,
www.PartnershipRepresentative.com, November 30, 2020
"IRS Kicks Off Post-Altera Audit Adjustments", with J. Clark Armitage, Leighanne Scott, and Elizabeth J. Stevens, Caplin & Drysdale Client Alert, September 21, 2020
"BLOG: Centralized Partnership Audit Regime Website Launched by IRS", www.PartnershipRepresentative.com, September 8, 2020
"IRS Will Continue Captive Insurance and Syndicated Conservation Easement Examinations Despite Covid-19 Pandemic", with Rachel L. Partain and Christopher S. Rizek, Caplin & Drysdale Client Alert, April 27, 2020
"Partnership Filing Relief", with Mark D. Allison, Christopher S. Rizek, James E. Salles, and Jonathan R. Black, Caplin & Drysdale Client Alert, April 13, 2020
"BLOG: IRS Issues LB&I Memorandum",
www.PartnershipRepresentative.com, April 7, 2020
"Captive Soft Letter", with Christopher S. Rizek, Rachel L. Partain, and Jonathan R. Black, Caplin & Drysdale Client Alert, March 31, 2020 Click here for a full list of publications.
