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The Internal Revenue Service (IRS) recently issued two private letter rulings (PLRs) that may be interesting for tax-exempt organizations that engage in political activity.

In the first ruling, the IRS held that a company could not deduct payments made to charity under a PAC matching contribution program as an “ordinary and necessary business expense.”  While the Internal Revenue Code already prohibits income tax deductions for political contributions, the company requested a PLR holding that the charitable contributions are deductible business expenses.  In rejecting the deduction, the PLR reasoned that “the contributions to [the] PAC and [the company’s] matching contributions are inextricably linked,” because the company would not have donated to the charity but for the employees’ contributions to the PAC.   Plus, the letter held, the matching program is intended to incentivize contributions to the PAC,  thus the charitable contributions are clearly “in connection with a political campaign” and not deductible.

The PLR comes on the heels of the FEC’s surprise approval of 2-to-1 corporate charitable PAC match programs this past January and provides some clarity into the tax implications of such matching programs. While campaign finance law now clearly allows corporations to grow their PACs by sponsoring charitable matching programs to incentivize giving, these programs should be viewed with eyes wide open: charitable contributions that help pad a corporate PAC’s coffers are not deductible business expenses.

In a separate ruling, the IRS issued a PLR late last year formally rejecting an organization’s qualification as a 501(c)(4) social welfare organization because it failed to adequately explain what social welfare activities it would undertake.  The organization  applied for (c)(4) status, claiming that its sole activity in the prior year was to hold a candidate forum and that it had no future activities planned.  The organization also acknowledged that it planned to spend money to influence elections, although that was not its primary purpose. The organization repeatedly ignored IRS requests for additional information to verify the social welfare activities of the organization.

Unlike 501(c)(3) charitable organizations, 501(c)(4) organizations may conduct some political activity as long as it is not the organization’s primary purpose.  501(c)(4)s are a common vehicle for lobbying activity, in the form of direct and grassroots advocacy, and some political expenditures; however, the PLR is an important reminder that a (c)(4) must engage in some social welfare activities, which do not include intervention in campaigns for or against candidates.

The PLR also emphasizes the importance of prospectively explaining to the IRS the exempt activities the organization plans to undertake.  While the letter acknowledged that “candidate forums” and similar activities “may meet the definition of social welfare by furthering voter education purposes,” it still faulted the organization for failing to describe its “planned activities for the future.”

Finally, the letter serves as a cautionary tale for (c)(4)s that failure to respond to questions by the IRS could result in the denial of tax-exempt status.  We note that the organization had the option to “self-declare” tax-exempt status as a 501(c)(4) organization rather than filing an application with the IRS.

Photo of Susan Leahy Susan Leahy

Susan Leahy has advised tax-exempt, nonprofit organizations on tax and corporate governance matters for over 25 years. She assists organizations in obtaining and maintaining tax-exempt status and advises boards and senior executives on a range of governance policies and procedures.

In her work…

Susan Leahy has advised tax-exempt, nonprofit organizations on tax and corporate governance matters for over 25 years. She assists organizations in obtaining and maintaining tax-exempt status and advises boards and senior executives on a range of governance policies and procedures.

In her work with tax-exempt organizations that operate in the United States, as well as internationally, Susan regularly:

Counsels clients on the tax implications involving:

Self-dealing, inurement, and impermissible private benefit to individuals and for-profit companies;
Lobbying, and political activities;
Unrelated business income tax;
Excess benefit transactions and compensation of executives;
Joint ventures and relationships with for-profit organizations;
Mergers of tax-exempt organizations and the acquisition or donation of assets; and
Corporate sponsorship.

Advises nonprofit boards of directors, board committees, and management with respect to:

Corporate formation and good governance principles;
Preparation for board and committee meetings; and
Conflicts of interests.
Provides guidance on state corporate and tax compliance for nonprofit organizations.

“Susan has been my ‘Go-To’ attorney for adept legal strategy and guidance for over 20 years. Susan skillfully led our organization’s volunteer leadership through a needed transition with compassion and sensitivity. Her legal assistance remains invaluable!” a nonprofit organization client noted.

“I highly value Susan’s expertise, responsiveness, and pragmatism,” said another client. “Her insight and advice have proven invaluable time and time again and remain integral to our ability to operate quickly and nimbly.”

Susan is the past chair of the Exempt Organizations Committee of the District of Columbia Bar and a member of the American Bar Association. Susan received her J.D. from Catholic University of America, Columbus School of Law and a B.B.A. from St. Bonaventure University.

Photo of Matthew Shapanka Matthew Shapanka

Matthew Shapanka is a strategic policy and regulatory attorney who helps technology companies and other businesses navigate complex, high-stakes legislative, regulatory, and enforcement matters at the intersection of law and politics. Drawing on 15+ years of experience across private practice, the U.S. Senate…

Matthew Shapanka is a strategic policy and regulatory attorney who helps technology companies and other businesses navigate complex, high-stakes legislative, regulatory, and enforcement matters at the intersection of law and politics. Drawing on 15+ years of experience across private practice, the U.S. Senate, state government, and political campaigns, Matt develops comprehensive policy strategies that identify regulatory risks and position clients to shape policy outcomes.

Public Policy and Regulatory Strategy

Matt serves as a strategic advisor to Fortune 200 companies on emerging technology policy, including artificial intelligence regulation, connected and autonomous vehicles, semiconductors, IoT, and national security matters. He translates complex legal and technical issues into actionable legislative and regulatory strategy, building the policy frameworks and advocacy infrastructure that enable clients to influence policy. He develops policy collateral for federal, state, and international advocacy, coordinates multi-stakeholder coalitions, and represents clients before Congress, federal agencies, and state legislative and regulatory bodies.

His technology policy experience includes securing unprecedented Presidential intervention in the $118 billion Qualcomm-Broadcom transaction (for which Covington was recognized as The American Lawyer 2019 “Dealmakers of the Year”), advising Fortune 200 companies on Bureau of Industry and Security connected vehicle rules, and counseling major internet platforms on autonomous vehicle policy across dozens of states.

Matt leads Covington’s state public policy practice, managing complex multistate legislative and regulatory advocacy campaigns. His state-level work includes securing a last-minute amendment to California’s 2023 money transmitter legislation on behalf of a fintech client and representing major technology companies on state AI, autonomous vehicle, and political advertising compliance matters across dozens of jurisdictions.

Matt rejoined Covington after serving as Chief Counsel for the U.S. Senate Committee on Rules and Administration under Chairwoman Amy Klobuchar (D-MN), where he negotiated the landmark bipartisan Electoral Count Reform Act – legislation that updated presidential election certification procedures for the first time in nearly 140 years. He also oversaw the Committee’s bipartisan January 6th investigation, developing protocols that resulted in unanimous passage of new Capitol security legislation.

Both in Congress and at Covington, Matt has prepared dozens of corporate executives, nonprofit leaders, academics, and presidential nominees for testimony at congressional committee hearings and depositions. He is a skilled legislative drafter and strategist who has composed dozens of bills and amendments introduced in Congress and state legislatures, including many that have been enacted into law.

Election and Political Law Compliance and Enforcement

As a member of Covington’s Chambers-ranked (Band 1) Election and Political Law practice, Matt advises businesses, nonprofits, political committees, candidates, and donors on the full range of federal and state political law compliance matters, including:

Election and campaign finance laws
Lobbying disclosure
Government ethics rules
The SEC Pay-to-Play Rule

He also conducts political law due diligence for M&A transactions, counsels major political funders and donors in compliance and enforcement matters, and represents candidates, ballot measure committees, and donors in election disputes and recounts.

Before law school, Matt served in the administration of former Governor Deval Patrick (D-MA), where he worked on policy, communications, and compliance matters for federal economic recovery funding awarded to the state. He has also staffed federal, state, and local political candidates in Massachusetts and New Hampshire.