Attorney Jessica Ledingham

About Jessica Ledingham

Hello, I’m Jessica aka Jess.
240 673 6869

“I’m Jessica aka Jess.  I’m passionate about Tax Law and have taken it as my life journey to make taxes simple and not overwhelming for individuals and businesses.  I have helped numerous avoid serious challenges with the IRS, and I have saved Millions of Dollars for my clients.  Do not hesitate to reach out to me and I’ll be happy to help!”

My Story

Prior to opening up my firm I honed my skills in the tax industry for seven years, representing all types of taxpayers from individuals and small business owners to Fortune 500 companies. In December of 2022, I left Willkie Farr Gallagher, LLP, with a mission to connect with every client I represent.

After I received my Tax LL.M. (Master of Laws) from the Georgetown University Law Center, I clerked for the Honorable Ronald Lee Buch of the U.S. Tax Court. Since my time at the Tax Court, I honed mskills in the various areas of the legal profession. I began my career in the international corporate tax group at PricewaterhouseCoopers in New York, NY, where I gained insight into tax law from the compliance perspective. I partnered with corporate tax planning and operations teams to assist in the compliance of large corporate taxpayers and defense of their positions on audit.

Since my time at the accounting firm, I worked in “Big Law” and represented individuals, corporations, and partnerships at all stages of an IRS examination, at appeals, and Tax Court in connection with federal income tax reporting and charitable contribution deductions.

​I received my Tax LL.M. (Master of Laws) from the Georgetown University Law Center on a merit scholarship. During that time, I spent a semester as a research fellow at the Council on State Taxation and another semester as a student extern at Pillsbury. I received my J.D. from the University of Nebraska College of Law with distinction. I received my B.A. in Economics from the University of Colorado-Denver with University honors.

​When I am not working, my husband and I are constantly on the go. Due to his time in the U.S. Marine Corps, we volunteer at various veteran organizations in addition to Experience Camp, a camp for children that have lost a parent or guardian. For fun we practice photography and go kayaking.

​I love my job as a tax attorney and my favorite part is being a reliable source of information and a steady hand for my clients.
Over the past 5 years my work included the following matters:

  • Represented event rental 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.
  • Represented a fast-food restaurant and its owners in an appeal of an audit of the company.
  • Represented a small business and its owners in an audit of the company.
  • Researched sales and use tax implications for event planners that provided services and rentals.
  • Filed case in the Superior Court of DC and received a $300,000 refund for client.
  • Assisted loved ones of a decedent in closing the probate of an estate with15 years of unfiled taxes.
  • Represented individual in a trust fund penalty recovery case.
  • Drafted memorandums pertaining to the Employee Retention Credit.
  • 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.
  • Represented insurance corporation and negotiate with opposing counsel the terminology and provisions for collateral arrangements, security documentation, and framework agreement.
  • Reviewed and edit employee handbook of a 501(c)(3), ensuring their compliance with current laws.
  • Drafted contracts with independent contractors for a 501(c)(3).
  • Represented individuals and businesses before the IRS during the examination of their prior filed tax returns, which includes managing relations with the client, collecting documentation, communicating effectively with the IRS, and drafting efficient IDR responses.
  • 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.
  • Reviewed the work of other associates before submission, such as petitions, IDR responses, and briefs.
  • 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.
  • Represented a trust in a proceeding in front of U.S. Tax Court.
  • Assisted a 501(c)(3) in its organization documentation, in receiving 501(c)(3) status, and ensuring full compliance with the Code for tax years 2018, 2019, and 2020.
  • 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).

When I am not working, my husband and I are constantly on the go. Due to his time in the U.S. Marine Corps, we volunteer at various veteran organizations in addition to Experience Camp, a camp for children that have lost a parent or guardian. For fun we practice photography and go kayaking.

​I love my job as a tax attorney and my favorite part is being a reliable source of information and a steady hand for my clients. 

Speaking Engagements and Publications

Speaking Engagements

ABA Tax Meeting Panelist, February 2023 – Basics and Advanced Issues Regarding IRS Liens and Levies, & Hot Topics in Tax Collections

Check out my latest Articles

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Call a Maryland Tax Attorney Jessica Ledingham Right Away

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