Andrea Darling de Cortes

Overview

Andrea Darling de Cortés advises U.S. and non-U.S. high-net-worth individuals, families and closely held businesses on international tax planning, cross-border income and estate tax matters, international tax compliance and tax controversy matters. She helps clients structure U.S. investments, navigate U.S. tax obligations and reporting requirements and address complex international tax issues involving multiple jurisdictions.

Andrea helps clients with U.S. and non-U.S. assets on a broad range of planning matters. Her experience includes U.S. income and estate tax planning for non-U.S. individuals, pre-immigration tax planning, foreign investment in U.S. real property, U.S. trade or business analysis and planning related to the incentives available under Puerto Rico's Act 60. Her work frequently extends beyond tax advice to include the legal, transactional, operational and practical considerations that accompany international wealth and business planning.

A significant part of Andrea's practice involves helping taxpayers address historic international tax and reporting issues. She has guided more than 1,000 taxpayers through IRS Voluntary Disclosure Programs and streamlined Filing Compliance Procedures. Her work includes addressing offshore reporting matters, including Report of Foreign Bank and Financial Accounts (FBAR), Form 8938, Forms 5471 and 3520, Passive Foreign Investment Company (PFIC) reporting and other international information return requirements. She handles matters ranging from compliance corrections to complex disclosure projects involving substantial offshore assets and multinational family structures.

Before joining Holland & Knight, she was a tax attorney with a boutique international tax law firm. Her experience across forward-looking planning and hands-on compliance experience enables her to help clients structure cross-border affairs while also addressing past reporting issues.

Representative Experience

Advised a Swiss-based family office owning several hundreds of millions of dollars in Florida real estate with respect to restructuring alternatives resulting from U.S. tax reform
Advised a Swiss-based investment group with substantial U.S. real estate holdings as to structuring cross-border compensation and advising on projected real estate sales to mitigate Foreign Investment in Real Property Tax Act of 1980 (FIRPTA) taxation
Advised several high-net-worth families regarding pre-residency planning to mitigate U.S. income and estate tax exposure on global holdings

Completed a multifaceted international succession plan on behalf of a high-net‑worth nonresident alien living in a tax-advantaged jurisdiction with respect to U.S. tax advice for structuring family and charitable succession plan
Served as co-counsel with respect to advising a foreign-based client with a net worth in excess of $1 billion with respect to succession planning to both U.S.-resident and nonresident successors, including advice with respect to mitigating U.S. tax through various developed strategies over a one‑year term
Advised a foreign fiduciary with respect to U.S. income and estate tax implications of offshore trust with U.S. beneficiaries to obtain step-up in basis of trust assets on demise of foreign trust settlor

Provided a high-net-worth nonresident alien client with U.S. tax advice to complete unfreezing of client's Swiss bank account held with a Category 1 Swiss bank currently in negotiations with the U.S. Department of Justice
Served as lead counsel to client group in an Internal Revenue Service (IRS) examination of foreign accounts held by family partnership, resolving such case with a "no change" finding
Provided cross-border tax advice with respect to an elderly dual citizen with previously undeclared assets in excess of $20 million; regularized U.S. tax and reporting via traditional IRS Service Center filing based on U.S. CPA reliance and reasonable cause defense
Negotiated a change in accounting method for an Offshore Voluntary Disclosure Program (OVDP) client with Egyptian blocked income to defer U.S. income tax on Egyptian financial accounts and income producing real estate
Served as lead counsel on several hundred taxpayer disclosures under IRS Offshore Voluntary Disclosure Programs, Streamlined Foreign Offshore Procedures and Streamlined Domestic Offshore Procedures, Delinquent International Information Return Submission Procedures, Delinquent Report of Foreign Bank and Financial Account (FBAR) Submission Procedures and IRS Service Center filings
Advised and successfully resolved several IRS examinations of taxpayers selected for IRS review as a result of the IRS Large Business and International OVDP Declines-Withdrawals Compliance Campaign

Credentials

Education

Marquette University Law School, J.D.
Marquette University, MBA, Business Administration
Marquette University, B.S., Business Administration

Bar Admissions/Licenses

Florida
Wisconsin

Memberships

Society of Trust and Estate Practitioners (STEP)
International Fiscal Association
American Bar Association, Business Law Section, Section of Taxation, Section of International Law
Tampa Bay Business and Professional Women

Honors & Awards