Philip Karter

Practice Areas

Tax

Tax Controversy & Litigation

Qualified Opportunity Zones

Captive Insurance Companies

Commercial Litigation

Career

Philip Karter specializes in tax controversy and tax litigation matters. In his 38-year career, Mr. Karter has litigated Federal tax cases in the United States District Courts, the United States Tax Court and the United States Court of Federal Claims, and argued in the United States Court of Appeals in multiple circuits. His range of trial experience, which includes dozens of jury and non-jury cases tried to judgment, encompasses a wide variety of complex and high-profile tax matters, a number of which have involved issues of first impression. Mr. Karter's deep experience in the tax controversy and litigation process, working both for and against the government, also provides him with valuable insights on how to structure and document transactions to avoid future tax disputes or, if such disputes are inevitable, to position such transactions in the best possible light to successfully withstand IRS scrutiny and challenge.

Prior to joining Chamberlain Hrdlicka in 2007, Mr. Karter was a partner at Miller & Chevalier and formerly served as a trial attorney with the U.S. Department of Justice Tax Division, where he was honored with the Department's Outstanding Attorney Award.

Mr. Karter also is one of a select number of attorneys recognized as a national authority in tax controversy and litigation by Chambers USA and the US Legal 500 Litigation and Tax Guides and is the only federal tax controversy attorney based in Pennsylvania to receive national recognition from the prestigious Chambers ranking publication.

Chambers also has ranked Chamberlain Hrdlicka as one of the top tax controversy law firms in the United States for the 15th consecutive year, which coincides with Mr. Karter’s joining the firm. He is also perennially named in the Best Lawyers in America®, one of the legal profession’s oldest and most respected peer-review publications, and recognized as “Lawyer of the Year” in Tax Litigation and Controversy for Philadelphia in the 2019 edition.

Mr .Karter has spoken on a variety of tax issues before the American Bar Association's Section of Taxation, the Tax Executives Institute, the Federal Bar Association, the New York University School of Law, the Georgetown University Law Center, The Southern Federal Tax Institute, the Palm Beach Tax Institute, and various state bar and professional associations.

In addition to his long career in tax controversy and litigation, Mr. Karter has worked for many years on numerous tax planning matters, with a particular emphasis on real estate investment partnerships. He presently works with real estate developers and investors in Qualified Opportunity Zone (QOZ) projects authorized by Internal Revenue Code §1400Z. Mr. Karter also maintains an active practice assisting companies establish both § 831(a) and § 831(b) captive insurance arrangements.

Professional Memberships

American Bar Association

Pennsylvania Bar Association

Philadelphia Bar Association

Publications

Publications

"Successfully Orbiting the Mothership in a Satellite Office"

Article by Phil Karter on "Successfully Orbiting the Mothership in a Satellite Office"

Legal Intelligencer, April 22, 2022

“Are Your Clients Prepared for a Wave of IRS Audits?”

Article by Phil Karter and Kevin Sweeney on “Are Your Clients Prepared for a Wave of IRS Audits?” Pennsylvania CPA Journal, December 2021

"Successfully Navigating the Client Transition Conundrum"

Article by Phil Karter on "Successfully Navigating the Client Transition Conundrum"

The Legal Intelligencer, September 10, 2021

"How to Successfully Transition to Private Practice from an In-House or Government Position"Article by Phil Karter and Mark Lubin on "How to Successfully Transition to Private Practice from an In-House or Government Position" Legal Intelligencer, June 30, 2021

“Thinking of Changing Firms? Here Are Some Questions to Ask at the Interview”

Article by Phil Karter and Stewart Weintraub on “Thinking of Changing Firms? Here Are Some Questions to Ask at the Interview” Legal Intelligencer, February 5, 2021

“Looking at Small Captives in a Post-Pandemic World"

Article by Phil Karter and Pat McCann on “Looking at Small Captives in a Post-Pandemic World" Bloomberg Tax, December 21, 2020

“IRS Audit Process: What You Need to Know” Article by Philip Karter on “IRS Audit Process: What You Need to Know” Pennsylvania CPA Journal/CPA Now Blog, November 16, 2020

“Should I Spend Money on a Business Development Coach? Advice for the New Partner"

Article by Phil Karter, Jennifer Karpchuk, and Kevin Sweeney on "“Should I Spend Money on a Business Development Coach? Advice for the New Partner" Legal Intelligencer, August 11, 2020

“IRS Letter 6336: To Respond or Not to Respond, That Is the Question”

Article by Phil Karter, Scot Kirkpatrick and Pat McCann on “IRS Letter 6336: To Respond or Not to Respond, That Is the Question” Tax Notes Federal, June 1, 2020

"The Letter in Question" Article by Phil Karter, Scot Kirkpatrick and Pat McCann on "The Letter in Question" Captive Insurance Times, May 27, 2020

“IRS Announcement Likely Overstates True Impact of Captive Insurance Settlement” in Bloomberg Tax, Article by Philip Karter and Patrick McCann on IRS Announcement Likely Overstates True Impact of Captive Insurance Settlement, Bloomberg Tax, February 28, 2020

What To Know About IRS Microcaptive Insurance Settlements in Law360

Law360, February 10, 2020

Identifying Exchange-Based Crypto in Bloomberg Tax Management Memorandum and Daily Tax Report, Bloomberg Tax Management Memorandum and Daily Tax Report, April 10, 2019

Tax Court Taketh Away While Congress Giveth Back, FC&S Legal, May 15, 2018

To Self-Insure or Not to Self-Insure? That is the Question, Captive Insurance Times, April 6, 2018

Captive Investments Scrutinized Following Key Tax Court Ruling, Business Insurance, January 2018

Ready Or Not, New Partnership Audit Rules Are Coming, Professionalisms Resources Thinking Aloud

The Tax Treatment of Tokens: What Does it Betoken? Tax Notes, September 11, 2017

What to Do When the IRS Comes Knocking, A 'To Do' List for Facilitating a Smooth and Robust Audit Defense, Corporate Counsel, June 2017

"IRS Access to Computerized Records of Corporate Taxpayers," 87 Journal of Taxation (September 1997).

" U.S. Officials’ Latest Proposals to Curb ‘Abusive Tax Shelters’ Could Affect Legitimate Cross-Border Transactions," Journal of International Tax Planning (March 2000).

Co-author of "Transfer Pricing for Services," Transfer Pricing Methods - An Applications Guide," John Wiley & Sons (2004).

“The Role of Economic Substance In Tax Shelter Controversies,” 19 The Corporate Counselor 8 (January 2005).

"What to Do When the IRS Comes Knocking - A 'To-Do' List for Facilitating a Smooth and Robust Audit Defense," Corporate Counsel Magazine, (June, 2017)

Ready Or Not, The New Partnership Audit Rules are Coming (December 2017)

Captive Investments Scrutinized Following Key Tax Court Ruling (January 2018)

To Self-Insure or Not to Self-Insure? That is the Question (April 2018)

How to Mount a Tax Defense for Unreported Crypto Income (April 2018)

Specifically Identifying Exchange-Based Crypto: An Old Solution to a New Problem, Bloomberg Tax (April 2019)

Blog Posts

2018 CAPITAL GAIN DEFERRAL OPPORTUNITY

Tax Blawg, June 25, 2019

Is There Trouble in the Deep End of the Pool for Small Captives after Reserve Mechanical v. Commissioner? Tax Blawg, November 9, 2018

Filing Tax Returns During the Silly Season,Tax Blawg, October 7, 2018

Quality Stores Day Of Reckoning Draws Near – What Should Employers Be Thinking About?, Tax Blawg, August 16, 2018

Taxpayers With Unreported Cryptocurrency Gains Should Start Thinking About Filing Qualified Amended Returns – And Soon, Tax Blawg, February 27, 2018

New Tax Bill May Eliminate Right to Deduct Fees Expended "In Connection with the Determination, Collection, or Refund of any Tax", Tax Blawg, November 3, 2017

Are Quiet Disclosures of Offshore Accounts Becoming Even Riskier? Tax Blawg, October 18, 2013

Apple’s Double Irish With A Dutch Sandwich Goes Down Easy with SEC, Tax Blawg, October 9, 2013

Supreme Court Accepts Certiorari In Quality Stores, Tax Blawg, October 1, 2013

Cleaning Up After The Elephants - A Practical Reminder On Document Preservation Policies and Litigation Holds In Tax Disputes, Tax Blawg, September 3, 2013

Sixth Circuit Moves The Ball Forward For Companies Seeking FICA Tax Refunds On Supplemental Unemployment Compensation Benefit Payments, Tax Blawg, January 9, 2013

Could The New Economic Substance Statute Apply To End-Of-Year Stock Sales And Repurchases?, Tax Blawg, December 28, 2012

IRS Records Retention Requirements In The Age Of Metadata,Tax Blawg, December 16, 2011

Musings in the Aftermath of the First Schedule UTP Filing Season,Tax Blawg, December 8, 2011

The Reporting Requirements for Deferred Tax Assets Under Schedule UTP: IRS Instructions Muddy The Waters,Tax Blawg, November 23, 2010

The Tax Workpapers Conundrum - Will “Justice” Kagan Accept What Solicitor General Kagan Opposed?, Tax Blawg, July 1, 2010

Squib Notes: Venerable “Kovel Rule" May Be Under New Attack, Tax Blawg, May 10, 2010

Trust but Verify - Proposed Schedule UTP and the Implications to Attorney Work Product

Tax Blawg, April 20, 2010

The Subliminal Message Underlying Announcement 2010-09,Tax Blawg, March 12, 2010

Son of BOSS Case Highlights Ongoing Dispute Over Application Of The Valuation Misstatement Penalty, Tax Blawg, March 12, 2010