Cassandra S. Bradford

Sandy’s practice is focused on domestic tax controversy matters. She represents taxpayers before the Internal Revenue Service, Department of Justice, and state taxing authorities at every stage of dispute. She advises clients through examinations and investigations, administrative appeals, Tax Court litigation, litigation in other federal courts, appellate proceedings, and collections, helping them manage risk and develop practical strategies for resolving challenging tax issues.

Her experience spans a broad range of tax controversy and litigation matters, including charitable donation and other valuation disputes, estate tax disputes, hobby losses, employment and payroll taxes, excise taxes, Employee Retention Credit (ERC) claims, conservation easements, partnership audits, transfer pricing, offshore compliance and foreign account and asset reporting, convertible tax bonds, entity classification elections, captive insurance arrangements, gift taxes, worker classification, reasonable compensation, cannabis tax issues, penalty abatement, COVID interest relief, innocent spouse, installment agreements, offers in compromise, and state tax disputes. Sandy has worked with individuals, limited liability companies, S-corporations, C-corporations, multinational corporations, trusts, partnerships, exempt organizations, and more.

As IRS enforcement priorities, procedural rules, and tax administration practices continue to evolve, Sandy helps taxpayers anticipate and respond to developments that can affect examinations, appeals, and litigation outcomes. She advises clients on emerging compliance challenges, jurisdictional and procedural issues, and strategic considerations that arise throughout the dispute process. Her experience includes matters involving the Compliance Assurance Process (CAP), challenges to Treasury regulations, private letter rulings, equitable tolling, and other complex issues that shape modern tax controversy practice.

Sandy regularly shares insights on tax controversy developments through presentations and educational programs for tax professionals, businesses, and advisors. Her speaking topics include IRS audits and appeals, ERC litigation, partnership audits, conservation easements, economic substance, disaster-related interest and penalty relief, artificial intelligence in tax administration, and significant legislative and regulatory developments affecting taxpayers.

Before joining Eversheds Sutherland as a Tax Partner, Sandy spent a decade with a tax-focused law firm, progressing to shareholder during her tenure. Earlier in her career, she served as a student attorney and graduate research assistant with the Philip C. Cook Low-Income Taxpayer Clinic, where she represented low-income taxpayers in federal tax disputes.