M&A is where strategy meets scrutiny—are you prepared for both? Mergers and acquisitions (M&A) represent transformative events in the lifecycle of a business. Whether buying or selling a business, these complex transactions require careful strategic planning, regulatory foresight, and thoughtful integration to ensure long-term success. At Gonzalo Law, we serve as trusted legal and strategic advisors to businesses navigating the nuanced terrain of M&A, particularly under New York law, which offers a robust legal framework for such deals.
This article explores the key phases of M&A transactions, real-world and hypothetical examples, recent changes under the Trump Administration, and five considerations often overlooked in conventional legal counsel.
I. Pre-M&A Planning and Strategy Development
Pre-transaction planning is critical. Businesses that approach M&A with a clear understanding of their goals, risks, and the regulatory landscape are better positioned to maximize value, reduce exposure, and ensure smoother execution throughout the transaction lifecycle. Early planning enables companies to align their acquisition or divestiture strategy with long-term business objectives, whether that means expanding into new markets, acquiring talent or technology, or unlocking synergies.
A well-defined M&A strategy should begin with internal alignment. Executive leadership, legal, finance, and operations teams must be unified on key priorities—such as valuation expectations, acceptable risk thresholds, preferred deal structure, and post-closing integration goals. Misalignment in the early stages often leads to costly delays or deal failure. Equally important is conducting a robust self-assessment to identify potential vulnerabilities. This may include reviewing outstanding litigation, intellectual property rights, contract obligations, employment matters, and financial liabilities. For sellers, this process—often called “sell-side due diligence”—can help uncover and address issues before they are discovered by buyers, preserving leverage and avoiding renegotiation of terms.1
For buyers, pre-transaction planning involves understanding the target company’s business model, competitive position, and culture. Identifying potential red flags early on—such as regulatory exposure, lawsuits, financial distress, data privacy violations, or unfavorable tax positions—allows for better risk allocation and deal structuring.2 It also provides time to craft a negotiation strategy that reflects the value and liabilities uncovered during due diligence. From a legal perspective, advance planning allows for proactive
engagement with regulatory bodies, tax advisors, and financial institutions, ensuring all aspects of the transaction are synchronized. Under New York law, this phase is also critical for identifying jurisdiction-specific issues such as local licensing requirements, real estate transfer taxes, and compliance with state labor laws.
Ultimately, successful M&A outcomes hinge on thoughtful, proactive strategy well before a letter of intent is signed. At our firm, we guide clients through every step of this foundational phase, helping them anticipate obstacles, protect their interests, and move forward with clarity and confidence.
A. Risk Assessment and Regulatory Compliance Evaluation
A comprehensive risk assessment identifies legal, operational, and financial red flags that could derail a transaction. For example, during Amazon’s acquisition of Whole Foods, regulatory scrutiny focused on how the merger might affect consumer pricing and antitrust issues.3 Amazon proactively engages legal and economic experts to evaluate risks and mitigate concerns, resulting in a smoother regulatory review process.4
In New York, due diligence often considers state-specific liabilities, such as unpaid sales taxes, employee classification disputes, and local zoning regulations.5 Counsel should also assess cybersecurity risks, particularly for businesses dealing with personal data, as per the New York SHIELD Act.6
B. Structuring Deals to Maximize Tax Efficiency and Shareholder Value
Strategic deal structuring can significantly impact tax outcomes. Asset sales, stock sales, and mergers each have unique tax implications. For instance, asset sales may provide buyers with a step-up basis, allowing for future depreciation deductions, but can result in double taxation for sellers if structured improperly.
Under New York law, careful consideration must be given to the transfer of assets such as real property and licenses, which may trigger transfer taxes and require regulatory approvals. Our firm evaluates each client’s objectives to structure the deal—whether as a forward merger, reverse triangular merger, or asset purchase—to achieve optimal results.
II. Navigating Antitrust and Regulatory Approvals
The regulatory landscape for mergers and acquisitions is both complex and constantly evolving, particularly as governments worldwide seek to balance market efficiency with the protection of consumers and competition. In the United States, M&A transactions that meet certain financial thresholds must undergo mandatory pre-merger notification under the Hart-Scott-Rodino Antitrust Improvements Act (HSR Act).7 This process requires parties to file with the Federal Trade Commission (FTC) and the Department of Justice (DOJ), both of which have authority to review the transaction and assess its potential anticompetitive effects.8 Failing to comply with HSR requirements can result in significant civil penalties and transaction delays.9
The FTC and DOJ share jurisdiction over antitrust review and may conduct a “second request” for additional documentation, which can extend review timelines by months.10 These agencies assess whether a transaction would substantially lessen competition or create a monopoly in violation of Section 7 of the Clayton Act.11 While horizontal mergers—deals between competitors in the same industry—have traditionally drawn the most scrutiny, recent enforcement trends have expanded oversight to vertical mergers, where companies in different stages of a supply chain combine.12 A prominent example is the DOJ’s lawsuit seeking to block the AT&T-Time Warner merger, signaling a more aggressive stance on deals that could result in anti-competitive leveraging of market power across sectors.13
In addition to federal review, state attorneys general, especially in New York, are increasingly asserting their authority to challenge deals that impact regional markets.14 The New York Attorney General may invoke the Donnelly Act, the state’s primary antitrust law, to block or condition transactions with local economic effects, such as hospital mergers, retail consolidations, or real estate acquisitions.15
Companies also need to be mindful of Securities and Exchange Commission (SEC) rules, especially when transactions involve publicly traded companies. These regulations cover disclosures, fairness opinions, shareholder communications, and insider trading issues.16 For instance, if a public company is acquiring or being acquired, it must file proxy statements or tender offer documentation to comply with the Securities Exchange Act of 1934.17
At our firm, we guide clients through the review process. In cross-border deals, we ensure compliance with foreign regulatory regimes—including the European Commission’s Merger Regulation and CFIUS (for foreign investments involving U.S. companies)—to deliver seamless, compliant, and strategically sound transactions.
A. Engaging with Regulators
Early engagement with regulators is essential. Pre-merger notification under the Hart-Scott-Rodino (HSR) Act is a key step for larger transactions.18 Failure to comply can result in substantial penalties.19
B. Addressing Potential Competitive Concerns
Antitrust enforcement varies depending on the political climate. Under the Trump Administration, antitrust enforcement saw a shift toward vertical integration scrutiny.20 The DOJ’s lawsuit to block AT&T’s acquisition of Time Warner illustrated a more aggressive stance on vertical mergers.21 The plaintiff in these anti-trust lawsuits carries the burden to demonstrate that the proposed merger harms consumer welfare and suppresses market competition.22
In New York, the state’s antitrust laws—such as the Donnelly Act—may also apply. The Attorney General may independently investigate deals with local market impact, particularly in sectors such as healthcare and retail. It is important to talk with legal counsel as you prepare for these deals to coordinate federal and state-level compliance strategies.
III. Post-Merger Integration Strategies
Closing the deal is only the beginning. Effective integration is crucial to realizing the full value of a merger or acquisition.
A. Aligning Corporate Cultures and Governance Structures
Culture clashes are a leading cause of post-merger failure.23 In a hypothetical scenario, consider a Brooklyn-based family-owned manufacturing firm acquired by a publicly traded Midwest conglomerate. Despite synergies in product lines, the deal can flounder due to conflicting management styles and decision-making structures.
Our firm advises clients to develop integration plans that align governance policies, HR practices, and operational protocols to integrate effectively after the merger. We work closely with human capital consultants to ensure smooth transitions and avoid the loss of key personnel.
B. Ensuring Regulatory Compliance Post-Merger
Post-closing compliance is equally critical. The SEC may require ongoing disclosures for public companies.24 Any environmental or labor law violations of the Seller may transfer to the buyer under successor liability doctrine, especially under New York law.25 We help clients conduct compliance audits, update policies, and train employees to reduce post-merger challenges.
IV. Real-World Example: Disney’s Acquisition of 21st Century Fox
Disney’s $71 billion acquisition of 21st Century Fox highlights the intricacies of large-scale M&A.26 The deal underwent extensive antitrust review in the U.S. and abroad, with Disney agreeing to divest certain assets to gain regulatory approval.27 The merger brought together massive intellectual property portfolios, required global legal coordination, and involved significant cultural integration.
Gonzalo Law has worked on cross-border transactions, managing jurisdictional regulatory filings, coordinating local counsel, and advising on intellectual property consolidation strategies. Our team can work with you if you find your company requires cross-border legal coordination.
V. Hypothetical: Tech Startup Acquisition in New York
As another example, imagine a fast-growing fintech startup based in New York City that has developed a proprietary blockchain platform for secure cross-border payments. After gaining traction with major institutional clients, the startup attracts acquisition interest from a leading European investment bank seeking to expand its digital asset capabilities. As the deal progresses, a range of complex legal and strategic issues arise, including compliance with New York’s SHIELD Act, ensuring a smooth transfer of intellectual property rights, managing cybersecurity risks associated with third-party data, and navigating export control laws due to the cross-border transfer of sensitive technology. This hypothetical scenario illustrates the multifaceted challenges that arise in tech-driven M&A deals and highlights the critical role of experienced counsel in anticipating risks and aligning transaction strategy with regulatory expectations. Imagine a New York-based fintech startup with proprietary blockchain technology being acquired by a European bank. Key legal issues might include:
- Export control compliance due to the cross-border transfer of technology.
- NY cybersecurity compliance, including third-party data-sharing under the SHIELD Act.
- Retention of key personnel and incentive restructuring.
- Ensuring GDPR compliance for European acquirers.
- Transfer of intellectual property rights and software licenses.
Our firm would approach this by conducting regulatory mapping, drafting robust IP assignment agreements, and negotiating earn-out structures tied to retention and product performance as needed. When considering your own company needs, legal counsel can work with you individually and design a strategy customized to your corporate legal needs.
VI. Five Novel Considerations Often Overlooked
Considering the five novel considerations often overlooked in M&A transactions is essential because they address emerging risks and opportunities that traditional due diligence may miss. As the business landscape evolves, factors such as environmental, social, and governance (ESG) compliance, AI accountability, remote work infrastructure, digital reputation, and cultural intelligence can significantly influence deal value and long-term success on the sale of a business in an M&A transaction. Ignoring these elements may lead to regulatory violations, integration failures, or reputational harm post-closing. By proactively addressing these modern challenges, businesses gain a competitive edge, ensure regulatory alignment, and position themselves for sustainable growth in an increasingly dynamic marketplace.
- ESG and Sustainability Metrics: As stakeholders demand more accountability, ESG factors increasingly influence deal value.28 Buyers should assess a target’s environmental practices and social governance disclosures.
- AI and Algorithmic Liability: Where AI is a core asset, due diligence must assess algorithmic bias, explainability, and compliance with emerging AI regulations, such as New York’s automated employment decision tools law.29
- Remote Work Infrastructure: Post-COVID, integration plans must address virtual workforce policies, cybersecurity risks, and remote management protocols.30
- Reputation Risk and Social Media Footprint: Online reputation can impact brand equity. A digital footprint audit should be part of due diligence, especially in consumer-facing sectors.31
- Cultural Intelligence: Especially in cross-border deals, cultural competence, including communication styles and negotiation norms—can make or break integration success.32
VII. Changes Under the Trump Administration
Once a company has considered these key changes in the M&A landscape, federal politics should also be analyzed. During the first Trump Administration, the regulatory environment for mergers and acquisitions experienced several key shifts that significantly impacted deal planning and execution. There was an increased focus on national security through expanded reviews by the Committee on Foreign Investment in the United States (CFIUS),33 heightened scrutiny of vertical mergers,34 and substantial changes to the U.S. tax code under the Tax Cuts and Jobs Act of 2017.35 These developments influenced how both domestic and international businesses approached transaction structuring, due diligence, and regulatory compliance, underscoring the importance of strategic legal counsel attuned to rapidly evolving policy landscapes. Under the Trump Administration, M&A enforcement policies saw notable shifts. These included the following changes:
- Increased scrutiny of vertical mergers (e.g., AT&T-Time Warner).36
- Emphasis on national security via CFIUS reviews, especially in tech and critical infrastructure sectors.37
- Streamlining tax regulations under the Tax Cuts and Jobs Act (TCJA), affecting how foreign income is taxed (GILTI, FDII, BEAT provisions).38
These changes required businesses to reevaluate deal structures, especially in cross-border transactions. The second Trump administration continues several of these policies and companies must continue to stay aware of updates. Our firm remains attuned to regulatory trends, advising clients with foresight on evolving policy risks.
VIII. Conclusion
M&A transactions are multifaceted, involving legal, financial, cultural, and regulatory dimensions. At Gonzalo Law, we provide end-to-end counsel—beginning with pre-M&A planning, navigating regulatory approvals, and culminating in post-merger integration. With a focus on New York law and global reach, we help clients navigate deals that build sustainable value.
Whether it is evaluating risks under the SHIELD Act, ensuring compliance with the Donnelly Act, or managing international approvals, we deliver strategic insight grounded in experience. Our strategic approach, combined with legal precision, positions clients for successful transactions in an increasingly complex business environment. In mergers and acquisitions, success favors the well-advised. Contact us today with any questions you may have at https://gonzalolaw.com/contact-us/.
References
1See BYRON E. FOX & ELEANOR M. FOX, CORPORATE ACQUISITIONS AND MERGERS § 2B.01 (2025).
2 See.id¡
3 Amazon”s.Whole.Foods.deal.under.scrutiny, BBC NEWS (July 24. 2017), https://www.bbc.com/news/business-40708880.
4 See.Marcus Lee, Amazon҂s.Regulatory.Compliance¿.A.Strategic.Play.for.Dominance.in.Trust‗Driven.E‗Commerce, AINVEST (June 5, 2025), https://www.ainvest.com/news/amazon-regulatory-compliance-strategic-play-dominance-trust-driven-commerce-2506/ (discussing Amazon’s strategic approach to regulatory compliance, particularly in its efforts to combat fake reviews)
5 See N.Y. COMP. CODES R. & REGS. tit. 20, § 537.0 (2024); Rebecca Stuart, Don”t.Forget.Employment.Diligence.When.Tying.Up.a.Merger, BLOOMBERG LAW (July 30, 2024), https://news.bloomberglaw.com/us-law-week/dont-forget-employment-diligence-when-tying-up-a-merger; N.Y. State Energy Research & Dev. Auth., Land Use and Regulatory Guidelines, Just Transition Site Reuse Planning Program, https://www.nyserda.ny.gov/All-Programs/Just-Transition-Site-Reuse-Planning-Program/Land-Use-and-Regulatory-Guidelines (last visited June 10, 2025).
6 N.Y. Gen. Bus. Law § 899-bb (McKinney 2020) (SHIELD Act).
7 15 U.S.C. § 18a (Hart-Scott-Rodino Antitrust Improvements Act).
8 Id¡
9 Id¡.at §18a(g).
10 Id¡.at §18(e).
11 15 USCS § 18.
12 See.Press Release, Fed. Trade Comm’n, FTC and DOJ Issue Antitrust Guidelines for Evaluating Vertical Mergers (June 30, 2020), https://www.ftc.gov/news-events/news/press-releases/2020/06/ftc-doj-issue-antitrust-guidelines-evaluating-vertical-mergers?utm_source=chatgpt.com.
13.See.generally.United States v. AT&T Inc., 310 F. Supp. 3d 161(D.D.C. 2018) (highlighting the DOJ’s more aggressive approach to vertical mergers by challenging AT&T’s acquisition of Time Warner despite the lack of horizontal overlap).
14 See.N.Y. Att’y Gen., Press Release, New York Attorney General James Moves To Block T-Mobile And Sprint Megamerger (June 11, 2019), https://ag.ny.gov/press-release/2019/new-york-attorney-general-james-moves-block-t-mobile-and-sprint-megamerger-0.
15 N.Y. Gen. Bus. Law § 340 (McKinney 2020) (Donnelly Act).
16 15 U.S. Code § 78 (the Securities Exchange Act of 1934).
17 Id¡
18 15 U.S.C. § 18a
19 Id¡.at § 18a(g)
20 See.generally.Press Release, Fed. Trade Comm’n, FTC and DOJ Issue Antitrust Guidelines for Evaluating Vertical Mergers (June 30, 2020), https://www.ftc.gov/news-events/news/press-releases/2020/06/ftc-doj-issue-antitrust-guidelines-evaluating-vertical-mergers?utm_source=chatgpt.com (updating vertical merger guidelines under President Trump for the first time since 1984).
21 See.United States v. AT&T Inc., 310 F. Supp. 3d 161(D.D.C. 2018) (illustrating the DOJ’s more aggressive approach to vertical mergers by challenging AT&T’s acquisition of Time Warner despite the lack of horizontal overlap).
22 See.id¡.at 189.
23 THOMAS FOX, THE COMPLIANCE HANDBOOK: A GUIDE TO OPERATIONALIZING YOUR COMPLIANCE PROGRAM § 7.10 (Matthew Bender ed., 2025).
24 Securities Exchange Act of 1934, § 13(a), 15 U.S.C. § 78m(a).
25 See.New York v. Nat’l Serv. Indus., Inc., 460 F.3d 201, 209 (2d Cir. 2006).
26 See.Press Release, U.S. Dep’t of Just., Justice Department Requires Walt Disney Company to Divest Twenty-Two Regional Sports Networks (June 27, 2018), https://www.justice.gov/archives/opa/pr/walt-disney-company-required-divest-twenty-two-regional-sports-networks-order-complete.
27 See.id¡.
28 Jeffrey Sparshott, ESG.Factors.Are.Now.Central.to.M™A.Deals, CFO (May 20, 2024), https://www.cfo.com/news/esg-environmental-social-governance-mergers-acquisitions-deloitte/718638/.
29 New York City Local Law No. 144, codified at N.Y. LAB. LAW § 860-a (McKinney 2023).
30 David Mapgaonkar et al., Beyond.Numbers¿.The.Critical.Role.of.Cybersecurity.in.M™A.Deals, WSJ RISK & COMPLIANCE (Jan. 15, 2025), https://deloitte.wsj.com/riskandcompliance/beyond-numbers-critical-role-of-cybersecurity-in-m-a-deals-6aba020c; Rico Brandenburg & Paul Mee, Cybersecurity.for.a.Remote.Workforce, MIT SLOAN MANAGEMENT REVIEW (July 23, 2020), https://sloanreview.mit.edu/article/cybersecurity-for-a-remote-workforce/.
31 Alexander Storozhuk, Online.Presence.And.Due.Diligence¿.Why.Your.Digital.Footprint.Matters, FORBES (June 12, 2023), https://www.forbes.com/councils/forbesbusinesscouncil/2023/06/12/online-presence-and-due-diligence-why-your-digital-footprint-matters/.
32 FOX, supra note 23.
33 See.Foreign Investment Risk Review Modernization Act of 2018 (FIRRMA), Pub. L. No. 115-232, §§ 1701–28, 132 Stat. 2173.
34 See.United States v. AT&T Inc., 310 F. Supp. 3d 161 (D.D.C. 2018); see.also.Press Release, Fed. Trade Comm’n, FTC and DOJ Issue Antitrust Guidelines for Evaluating Vertical Mergers (June 30, 2020), https://www.ftc.gov/news-events/news/press-releases/2020/06/ftc-doj-issue-antitrust-guidelines-evaluating-vertical-mergers?utm_source=chatgpt.com.
35 See Tax Cuts and Jobs Act, Pub. L. No. 115-97, 131 Stat. 2054 (2017).
36 See.AT™T.Inc¡, 310 F. Supp. 3d 161; see.also.FTC, FTC and DOJ Issue Antitrust Guidelines for Evaluating Vertical Mergers (June 30, 2020).
37 See FIRRMA, Pub. L. No. 115-232, §§ 1701–28 (2018).
38 See Tax Cuts and Jobs Act, Pub. L. No. 115-97, 131 Stat. 2054 (2017).
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