Alexander Apostolopoulos is a respected attorney based in New York City whose career reflects both academic distinction and professional accomplishment. Born in Berlin, Germany, Alexander Apostolopoulos relocated to the United States at the age of sixteen. He soon advanced academically, completing a Bachelor of Arts in Classics at Yale College, where he graduated summa cum laude. This academic achievement provided a robust foundation for his legal career. Alexander Apostolopoulos subsequently attended Harvard Law School, earning his Juris Doctor degree magna cum laude. His coursework included corporate and securities law, financial regulation, and tax law, and he gained valuable experience through scholarly interactions with notable legal minds, including collaboration with Senator Elizabeth Warren.
Professionally, Alexander Apostolopoulos began his legal career in 2011 at Sullivan & Cromwell as a tax associate. There, he developed expertise in transactional matters involving major corporations, such as AIG and Wells Fargo, with a focus on optimizing tax structures and strategic planning. His progression led him to a partnership at a leading multinational law firm in New York City, where Alexander Apostolopoulos provided counsel on significant transactions, including the $4.4 billion merger of Cano Health LLC with a SPAC. In addition to his legal practice, Alexander Apostolopoulos maintains interests in classical music, hiking, and national parks, demonstrating a disciplined commitment to personal growth and lifelong learning.
Today’s capital market involves deals that are often global and technical, and tax considerations often play a significant role in how to structure transactions. In transactions like mergers, Initial Public Offerings (IPOs), complex reorganization, and spin-offs, it is imperative upon the parties to obtain advice of competent tax counsel, because the consequences of “getting it wrong,” i.e., resulting in a transaction that was expected to be tax-deferred to, instead, become currently taxable, can be drastic in terms of high tax bills for corporations and/or shareholders.
The peculiar and delicate nature of these tax transactions makes tax opinions relevant. A tax opinion is a written statement from a tax specialist who explains how tax laws might apply to a particular transaction and, where relevant, the risks inherent in such transaction (e.g., because of uncertainty of how the tax laws apply to such particular transaction). Tax opinions help businesses to structure their deals in an efficient manner, ensure confidence among regulators and facilitators, while protecting businesses from penalties that might arise in the future.
In the context of publicly traded corporations undertaking transactions, tax opinions are sometimes required by regulation. According to the US Securities and Exchange Commission (SEC), companies are expected to include tax opinions in specific filings when a deal or offering has key tax implications for investors (and such tax implications must be described in the relevant filing). This requirement applies to transactions like mergers and acquisitions, spin-offs, or other transactions where tax outcomes might not be as straightforward. SEC expects that the tax disclosure (and related tax opinion) be written in such a way that the investor can rely upon it as part of the information that they use while they make decisions regarding whether to vote in favor or against the relevant transaction.
Tax opinions are also important because they help reduce tax-related penalties from the IRS. If a taxpayer takes a tax position that the IRS subsequently questions, a well-prepared tax opinion can be proof that the tax decision was made in good faith and with reasonable care. This can help avoid or reduce tax penalties. Obtaining an independent and professional tax opinion evidences the credibility of the taxpayer’s position and lowers their risk of having issues during IRS audits.
In many cases, contracts for mergers, acquisitions, or reorganizations require a favorable tax opinion as a “closing condition,” i.e., failing the issuance of such opinion permits the relevant party to withdraw from the transaction. This condition ensures that the transaction qualifies under the relevant tax laws and, generally, protects both parties. If new tax issues appear at the final stages, the opinion requirement induces the parties to revisit the terms of the deal, renegotiate, or even step away completely, preventing costly mistakes and protecting long-term interests.
Finally, tax opinions must meet the requirements of IRS Circular 230, which holds tax practitioners to certain professional standards. To comply when providing tax advice in written communications (including those provided electronically), the practitioner must, (a) base the written advice on reasonable factual and legal assumptions, including assumptions as to future events, (b) reasonably consider all relevant facts the practitioner knows or reasonably should know, (c) use reasonable efforts to identify and ascertain the facts relevant to written advice on each federal tax matter, (d) not rely upon representations, statements, findings, or agreements (including projections, financial forecasts, or appraisals) of the taxpayer or any other person if reliance on them would be unreasonable, (e) Relate applicable law and authorities to facts, and (f) not, in evaluating a Federal tax matter, take into account the possibility that a tax return will not be audited or that a matter will not be raised on audit.
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