Attorney Jessica Ledingham

Jessica Ledingham is an accomplished tax attorney who prides herself in being a reliable source of information and a steady hand for her clients. Ms. Ledingham’s practice centers around her defending her clients during IRS and state examinations, challenging assessments, and penalties, and litigating in the U.S. Tax Court and Federal District Court, against the IRS and the Department of Justice.  Her representation includes those of a sensitive nature in connection with a risk of the allegation of tax fraud.

Her practice includes representing her clients on collection matters such as offers-in-compromise, lien releases, installment agreements, innocent spouse petitions, and FBAR voluntary disclosures. Additionally, she has successfully represented her client in Maryland property tax appeals, Maryland State audits, and Washington D.C. refund suits. She is also experienced in obtaining and defending tax-exempt status for public and private non-profits.

Prior to starting Ledingham Law, Ms. Ledingham worked for Willkie Farr Gallagher, LLP and PricewaterhouseCoopers in New York, NY. Additionally, she received her Tax LL.M. (Master of Laws) from the Georgetown University Law Center and clerked for the Honorable Ronald Lee Buch of the United States Tax Court. 

Ms. Ledingham’s work is routinely recognized in various communities. She was listed in the Best Lawyers in America for Tax Law: Ones to Watch list for 2024 and 2025. Ms. Ledingham routinely speaks at state Bar Associations nationwide on various tax-related topics. She contributes to Forbes magazine and Tax Notes and is often sought for her expert commentary by Law360. She currently serves as the Chair of the American Bar Association Young Lawyers Division Tax Law Committee and is a Leadership Academy Fellow with the Maryland State Bar Association (MSBA).

Ms. Ledingham’s work includes the following matters:

• Represented individual during a trust fund penalty examination and successfully defended client against a $3,000,000 penalty.
• Filed case in the Superior Court of DC and received a $300,000 refund for client.
• Routinely filed refund requests and received refunds for clients in the State of Maryland.
• Represented individuals in the State of Maryland against criminal charges.
• Filed voluntary disclosure for clients that have unfiled taxes of 20 years.
• Successfully defended spouse during an innocent spouse claim.
• Represented company in Frederick County District Court for a criminal charge in association with sales and use tax.
• Represented individual in appealing to the State of Maryland in connection with failure to file employment taxes.
• Successfully represented individuals and businesses during Federal and state examinations.
• Researched sales and use tax implications for event planners that provided services and rentals.
• Filed 501(c)(3) and 501(c)(7) applications for corporations.
• Defended clients in Employee Retention Credit examinations.
• Reviewed tax documents and offered guidance regarding a merger between two US corporations.
• Represented insurance corporation and reviewed and summarized pension longevity documentation for business personnel.
• Represented insurance corporation in pension scheme transfer and draft and edit the collateral arrangements, security documentation, and reinsurance contracts.
• Reviewed and edit employee handbook of a 501(c)(3), ensuring their compliance with current laws.
• Drafted protest letters to submit to Appeals regarding the conservation easement charitable deduction under section 170.
• Represented individuals and businesses in front of the U.S. Tax Court, which included drafting and filing of petitions, replies, stipulations of fact, and briefs filed with the U.S. Tax Court.
• Engaged expert witnesses, interviewing all relevant parties to discover witnesses, prepping witnesses for depositions, and preparing witnesses for trial at the U.S. Tax Court.
• Drafted memoranda regarding complying with federal income tax reporting requirements, such as an:
  • Analysis regarding the excise taxes for the export of diesel fuel;
  • Explanation of the step-transaction and substance over form doctrines for a corporate reorganization;
  • Analysis of whether section 199A applies to a rental real estate enterprise; and
  • Analysis of the intricacies of the Bipartisan Budget Act of 2015.
• Assisted taxpayers with admittance into the voluntary compliance disclosure program.
• Represented a multinational corporation (MNC) in an appeal involving an R&E Credit of wages for a statistical sample of 75 employees in the semi-conductor industry.
  • Managed fellow associates and paralegals during the IRS Examination.
  • Drafted the first draft of the 200-page protest to IRS Appeals.
• Researched then wrote a technical memorandum for an MNC regarding whether a change in accounting methods was a regulatory election, as defined in section 301.9100-1(b).
• Analyzed applicable law and drafted a memorandum for an MNC regarding debt versus equity analyses of Islamic finance instruments and contracts for U.S. federal income tax return reporting.
• Researched section 451(b), as amended by the TCJA, and the proposed regulations (REG-104870- 18), and then presented to the firm’s tax group on the consequences of the “enforceable right to payment” language in the proposed regulations.
• Drafted a memorandum for an MNC regarding whether it was entitled to dividends received deductions under sections 245A and 245(a) for the 2019 taxable year.
• Drafted a memorandum for an MNC to explain whether a license of a film qualified for bonus depreciation under section 168(k) during the tax year 2018 and whether the MNC needed to file Form 8275-R, Regulation Disclosure Statement, if it reported the bonus depreciation on its Form 1120, U.S. Corporation Income Tax Return.
• Developed and delivered IRS Information Document Request responses for an MNC to explain:
  • why the MNC filed Schedules M-3 attributable to installment sales, accelerated tax depreciation, and discharge of indebtedness;
  • why the MNC reported income not effectively connected with the conduct of a trade or business in the United States on its Section I on its Form 1120 because one of the MNC’s subsidiaries requested a refund of some tax withheld;
  • why the MNC did not report certain subpart F income on its Form 5471, Information Return of U.S. Persons with Respect to Certain Foreign Corporations, specifically, in connection with sections 954(c)(3), (c)(6), (d)(1)(A), and (d)(1)(B);
  • how the MNC allocated and apportioned expenses under section 861
  • the foreign tax credits the MNC claimed on its Form 1118, Foreign Tax Credit.
• Determined the proper method of apportionment for an MNC’s tax year, then allocated the expenses among the different baskets under section 861 and the regulations thereunder.
• Created step-plans for MNCs for purposes of post-acquisition structuring, IP migration, foreign headquarters relocation, a section 368(a)(1)(D) reorganization, and a merger under section 708(b)(2)(A).