Gregory E. Gentry

M&A and Corporate Transactions

Greg has strong skills in complex transactions and in leading teams through a deal. He manages the disparate pieces of transactions with large teams of attorneys and corporate stakeholders, with sensitivity to the staffing and leverage models that are most cost-effective for clients. His practice includes advising clients on mergers and acquisitions, venture capital transactions, and a broad range of general corporate matters, and he is valued for his practical, business-oriented approach to navigating sophisticated transactions.

Representative Experience

• Led the $400 million acquisition of a national stop-loss insurance carrier and captive reinsurer. The regulatory and structural complexity of this deal involved acquiring a business operating across multiple jurisdictions and embedded within a broader multinational corporate structure. Greg was responsible for all aspects of the transaction, including diligence, negotiation of definitive agreements, and post-closing integration. The transaction included a high-value purchase price adjustment dispute involving complex actuarial inputs, which required both technical fluency and commercial judgment. The deal also required coordination of extensive multistate insurance regulatory approvals.
• Led the $115 million acquisition of a provider-owned health plan, with a dual-track structure and regulatory execution risk. The transaction required simultaneous closing of an equity acquisition and the novation of a Medicare Advantage H-Contract, subject to approval by CMS and multiple state regulators. Greg coordinated parallel workstreams involving regulatory approvals, transaction documentation, and operational readiness, ultimately achieving a December 31 closing that was critical to both parties’ financial and reimbursement objectives. The ability to align these interdependent processes under a fixed timeline was a key driver of the transaction’s success.
• Led the divestiture of a long-term-care insurance book of business through an assumption reinsurance transaction, involving approximately 1,300 policyholders across four states. In addition to managing sell-side diligence and negotiation of transaction agreements, Greg led parallel negotiations with multiple legacy reinsurers and retrocessionaires, some of which had undergone corporate changes since the original treaties were executed. Following signing, Greg remained closely involved through closing and post-closing, including securing multistate departments of insurance (DOI) approvals and supporting policyholder communications and transition arrangements. This transaction required sustained engagement across legal, regulatory, and operational dimensions.
• Led multiple late-stage financing rounds (Series D through G) for a value-based kidney care platform, including a $300 million Series G financing completed under a highly compressed timeline. These transactions required structuring solutions that balanced investor protections with founder and company objectives. One example of such structured solutions involved a secondary sale and equity exchange mechanism that enabled founder liquidity while avoiding dilution from a new primary issuance while ensuring the client obtained the most senior preferred equity position. The Series G round, in particular, required rapid execution under significant time pressure.
• Counseled on integration planning in connection with a multibillion dollar planned acquisition of a Blue Cross Blue Shield licensee. Greg advised a large, cross-functional working group on interpretation of transaction agreements and was responsible for integration planning across the legal, compliance, ethics, and government affairs functions. This required translating complex contractual provisions into actionable operational plans and coordinating stakeholders across disciplines.

In-House Experience

Formerly, Greg was associate general counsel at Elevance Health, where he supported the mergers and acquisitions, venture capital investments, joint ventures, and other strategic equity transactions of a Fortune 20 health insurance company.

Personal Interests

In his free time, Greg enjoys gardening, traveling with his family, and cooking. He values the opportunity these pursuits provide to spend quality time with loved ones and appreciate new experiences both at home and abroad.