Derek W Kaczmarek

Derek W. Kaczmarek

Derek Kaczmarek is a former IRS Office of Chief Counsel Senior Trial Attorney with significant trial experience. Representing clients in captive insurance, tax fraud, alleged tax shelters, issues of first impression, unreported income and expense substantiation audits, appeals and litigation.

Education & Credentials


DePauw University

B.A., 1997

Indiana University, Mauer School of Law

J.D., 2003
  • With Honors

Indiana University, Kelley School of Business

M.B.A., Finance, 2003

New York University School of Law

LL.M, Taxation, 2005

Bar Admission

  • Arizona
  • Nevada


  • AV Rated – Martindale Hubbell
  • Certified Tax Specialist – State Bar of Arizona
  • Cube Award – IRS Office of Chief Counsel award for outstanding litigation of a case
  • Bronze Medal Litigation Award – IRS Office of Chief Counsel award for career achievement in Tax Court
  • – perfect 10.0 rating

Prominent Assignments

Caylor Land & Development v. Commissioner, awaiting opinion – U.S. Tax Court – Issue of first impression involving deductibility of insurance expenses paid to a micro-captive insurance company pursuant to IRC 831(b).

Rainbow Tax Service v. Commissioner, 128 T.C. No. 5 (2007) – U.S. Tax Court – issue of first impression involving the definition of accounting to determine application of IRC 11(b)(2) flat-tax to a personal service corporation under IRC 448(d)(2).

Jones v. Commissioner, 146 T.C. No. 3 (2016) – U.S. Tax Court – Issue of first impression involving the treatment of income and expenses of an Arizona judge constituting a fee basis government official pursuant to IRC 62(a)(2)(C).

Purvis v. Commissioner, awaiting opinion – U.S. Tax Court – civil fraud case involving income derived from a purported Ponzi scheme. Issue of first impression involving IRC 6664 reliance on advice of a tax professional to defeat IRC 6663 penalty.

Slone v. Commissioner, T.C. Memo. 2016-115 – U.S. Tax Court – case involving application of Arizona uniform fraudulent transfer act and economic substance, substance over form and step transaction doctrines to a midco transferee liability case.

Estate of Giovacchini v. Commissioner, T.C. Memo. 2013-27 – U.S. Tax Court – case involving the valuation of approximately 2,500 acres in Lake Tahoe, CA and the relevance of a post-death sale in an estate tax case.

Ernle v. Commissioner, T.C. Memo. 2010-237 – U.S. Tax Court – civil tax fraud case involving multiple fraudulent schemes. Applied IRC 6663 to the use of false documents and submission of 1099-OIC forms with tax returns.

Fain v. Commissioner, 129 T.C. No. 11 – U.S. Tax Court – issue of first impression involving innocent spouse case pursuant to IRC 6015. Court determined the ability of an estate to intervene in an innocent spouse Tax Court case.

Estate of Evenchik v. Commissioner, T.C. Memo. 2013-34 – U.S. Tax Court – case involving the application of the qualified appraisal requirements of IRC 170(f) to a charitable donation.

Kline v. Commissioner, T.C. Memo. 2015-144 – U.S. Tax Court – case involving material participation in a Caribbean yacht charting business. Application of IRC 469 and Treas. Reg. 1.469-5T(a)(3) when using a charter management company.

Professional Involvement

  • Arizona Board of Legal Specialization (Tax)
  • State Bar of Arizona, Tax Section, Chair
  • Western States Bar Association, Arizona representative


  • Author, "IRS Passport Revocation - 260,000 and Counting..." Dickinson Wright Tax Blog, September 24, 2018 
  • Co-presenter, “Update on Captive Tax Controversies,” Delaware Captive Insurance Association 2018 Spring Forum, Rehoboth Beach, Delaware, May 14, 2018 
  • Contributing Author, Chapter TX5 Litigation with the IRS in Bankruptcy Court, Collier on Bankruptcy Taxation, 2014 – 2018
  • Co-Author, "Help Me Make it Through the Fight - Can State Regulation Help With the IRS?", Captive Review, 2018
  • Micro-captive Insurance and the IRS, State Bar of Arizona, 2017
  • IRS’s Attack on 831(b) Captive Insurance, The Nevada Lawyer, 2016 
  • Discussion of IRC 831(b) Captive Insurance Audits and Litigation, Western Regional Captive Insurance Conference, 2016
  • Nuts & Bolts of U.S. Tax Court Litigation, American Bar Association, Section of Taxation, 2016 Midyear Meeting
  • Present Tax Controversies: Navigating the Process, University Nevada-Las Vegas CLE Program, 2013
  • Effective Use of Expert Witnesses in the U.S. Tax Court, American Society of Appraisers, 2012
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