Tax Relief Tactics: Mastering IRS Penalties, Fines and Interest Abatement

Gray earned a B.S. from The University of Texas at Dallas (1998), an M.A. from the University of New England (2004), and his J.D. from Vanderbilt University (2007), where he was named to the Dean's List and received the Book Award in Criminal Procedure. He has been board certified as a Specialist in Appellate Practice by The Florida Bar since 2021. He is admitted in the State of Florida; the State of Georgia; the U.S. District Courts for the Northern, Middle, and Southern Districts of Florida and the Southern District of Georgia; the U.S. Courts of Appeals for the First, Second, Third, Fourth, Fifth, Sixth, and Eleventh Circuits; the United States Tax Court; and the United States Supreme Court.

Gray is a Board Certified Specialist in Appellate Practice with The Florida Bar (since 2021, a designation held by fewer than 1% of active Florida Bar members), is AV Preeminent rated by Martindale-Hubbell, and has been recognized as an elite appellate practitioner in Florida Trend magazine's Florida Legal Elite for Appellate Practice. His published work on SEC v. Jarkesy and its implications for tax penalty procedure has been cited by courts and practitioners as a leading treatment of the administrative law developments reshaping federal regulatory enforcement. His publications include "Jarkesy, Originalism, and the Future of Tax Penalties" (April 2026) and "Can Tax Promoter Penalties be 'Excessive Fines' Under the Eighth Amendment?" (October 2025).

Gray served as a federal law clerk in three courts — the U.S. District Court for the Southern District of Texas, the U.S. District Court for the Eastern District of Virginia, and the U.S. Court of Appeals for the Fourth Circuit — before building his appellate practice. He is an author on appellate and tax-penalty topics and participates in firm thought leadership, including a Columbia Law School Moot Court Program engagement. He accepts court-appointed counsel work under the Criminal Justice Act in the Sixth and Eleventh Circuits.

Gray's appellate practice spans federal tax controversies and APA-based challenges to federal agency action. His representative matters include serving as appellate counsel coordinating Jarkesy Seventh Amendment and Article III challenges across multiple Tax Court cases, including representation of the Center for Taxpayer Rights as amicus curiae before the U.S. Tax Court, the Eleventh Circuit, and the U.S. Supreme Court; serving as amicus counsel for the Center for Taxpayer Rights before the U.S. Tax Court in Silver Moss Properties, LLC v. Commissioner, briefing whether the Seventh Amendment right to a jury trial extends to fraud and accuracy penalties under Jarkesy; providing additional amicus briefing in the Eleventh Circuit and the Supreme Court in Hirsch v. United States on the Jarkesy issue; providing briefing support in a consolidated 13-case trial involving conservation easement donation partnerships facing substantial federal tax and penalty liability, including APA arbitrary-and-capricious review and valuation disputes; developing and briefing issues opposing retroactive application of IRS Notice 2017-10 under APA arbitrary-and-capricious review; serving as court-appointed counsel under the Criminal Justice Act in the Sixth and Eleventh Circuits representing indigent defendants in direct criminal appeals; serving as counsel in state and federal post-conviction proceedings, including habeas corpus petitions under 28 U.S.C. §§ 2254 and 2255; and serving as appellate and trial support counsel in a wide variety of state and federal disputes, including commercial litigation, family law, and insurance coverage.