Gerald T.Chichester

Gerald advises transactional risk insurers and underwriting teams on a broad range of issues that arise in connection with representations and warranties insurance and other transactional risk products in large M&A transactions. He advises and coordinates analysis to underwriters on legal, regulatory, compliance, tax, employment, intellectual property, privacy, cybersecurity, and operational risks identified during transaction diligence. He assists with the drafting and negotiation of policy language, exclusions, and coverage positions in complex or highly negotiated transactions. Gerald supports underwriting teams on deals involving heavily regulated industries, cross-border considerations, and heightened compliance exposure. He helps clients evaluate diligence sufficiency and identify areas where additional investigation or risk mitigation measures may be appropriate. He coordinates with deal counsel, brokers, underwriting teams, and other transaction participants to facilitate smooth execution under tight timelines.

Gerald has worked on transactions where diligence uncovered nuanced regulatory and operational risks late in the underwriting process, requiring rapid analysis and collaboration across multiple parties to develop commercially reasonable solutions before signing. He has also assisted underwriting teams in evaluating complex diligence records and translating technical legal findings into practical underwriting recommendations that aligned with both risk management and business objectives.

Every transaction presents a different combination of industry risks, deal structures, diligence quality, and business objectives, so Gerald tailors his approach to the specific legal needs of each matter and underwriting team. For some transactions, the key challenge may be evaluating a particularly complex regulatory or compliance issue. In others, it may involve assessing gaps in diligence, assisting in negotiating policy language under aggressive timelines, or coordinating efficiently with buyer’s counsel and underwriters across multiple workstreams. With every matter, Gerald shapes his litigation approach around the underlying transaction, the client’s appetite for risk, and the business implications of every strategic decision.

Clients can expect responsiveness, practicality, and a collaborative approach with Gerald. He continually looks for ways to improve efficiency, streamline issue-spotting, and support underwriting teams in fast-moving deal environments. Gerald not only understands the legal risks and underwriting issues involved in a transaction, but also appreciates the importance of maintaining productive working relationships throughout the process.