Generali's Leadership Transition and Strategic Reforms: Assessing Caltagirone's Legacy and Delfin's Challenges in Driving Sustainable Value Creation

The leadership transition at Assicurazioni Generali, marked by the departure of Alessandro Caltagirone and the evolving role of Delfin, has reshaped the insurer's strategic landscape. As the company navigates a complex interplay of governance reforms, ESG commitments, and shareholder dynamics, investors must assess whether these shifts will catalyze sustainable value creation or exacerbate internal fragmentation.

Caltagirone's Legacy: ESG as a Governance Tool

Alessandro Caltagirone's tenure (2020–2025) was defined by a strategic pivot toward ESG (Environmental, Social, and Governance) initiatives, framed as both a moral imperative and a governance lever. His alliance with Fondazione CRT, formalized in early 2025, underscored this approach. Together, they committed €10 million to Sicilian solar and wind projects, €50 million to a green venture capital fund for clean energy startups, and €20 million to Turin's “smart city” initiative. These moves were not merely altruistic; they were calculated to embed ESG criteria into Generali's corporate identity, countering Mediobanca's influence and aligning with institutional investor expectations.

Caltagirone's strategy also involved blocking competing initiatives, such as the proposed Generali-Natixis asset management partnership, which he viewed as incompatible with long-term sustainability goals. By leveraging his 6.9% stake, he positioned ESG as a non-negotiable pillar of Generali's strategy, even as critics argued this prioritized governance control over operational efficiency.

Delfin's Strategic Priorities: Governance Reform and Shareholder Value

Post-Caltagirone, Delfin—the vehicle of the Del Vecchio family—has emerged as a key architect of Generali's future. Holding a 9.9% stake and aligned with Mediobanca (via its 13% ownership), Delfin's priorities center on cost efficiency, technological modernization, and governance transparency. Its opposition to the Natixis deal reflects a preference for strategies that enhance profitability without compromising long-term stability.

Delfin's influence is amplified by Italy's new corporate governance law, which redistributes board seats proportionally in contested shareholder votes. This could enable Delfin to secure a larger board representation, challenging Mediobanca's dominance. However, its success hinges on navigating internal divisions, such as the exclusion of Caltagirone and his allies from key committees post-2025. The dissolution of the strategic operations committee—a former “control room” for high-impact decisions—has raised concerns about oversight gaps, particularly in ESG integration and risk management.

Challenges in Sustainable Value Creation

The post-Caltagirone era has exposed structural vulnerabilities in Generali's governance. The absence of a dedicated strategic oversight mechanism, coupled with the lack of a clear second-in-command, risks diluting the company's ESG momentum. For instance, the exclusion of Caltagirone's allies from the Innovation and Social and Environmental Sustainability Committee could weaken the cross-functional coordination needed to execute initiatives like the SME EnterPRIZE program or the Fenice 190 fund.

Moreover, shareholder activity—such as De Agostini's recent sale of 1.6 million Generali shares—signals potential investor skepticism about the company's direction. While Generali's “Lifetime Partner 27” strategy emphasizes climate resilience and digital transformation, the governance tensions may hinder its ability to balance profitability with ESG commitments.

Investment Implications

For investors, Generali presents a paradox: a company with ambitious ESG goals but a governance structure prone to internal conflict. The key question is whether Delfin can stabilize the board while preserving the ESG momentum Caltagirone initiated.

1. ESG Momentum vs. Governance Risks: Generali's ESG-linked grants increased by 15% in 2025, and its renewable project commitments rose by 35%. However, the lack of diverse board representation in ESG committees could undermine these efforts. Investors should monitor the company's quarterly reports and IVASS (Italian Insurance Supervisory Authority) assessments for signs of alignment.

2. Board Dynamics and Shareholder Influence: Delfin's potential to secure proportional board seats under the new Italian law could enhance governance transparency. However, if Mediobanca resists this shift, it may trigger further shareholder battles, increasing volatility.

3. Strategic Agility: Generali's “Next Level Plan” for 2025–2027 hinges on strategic agility. Investors should evaluate whether the board's current structure—lacking a vice president and relying on independent directors—can adapt to market changes without sacrificing long-term vision.

Conclusion: A Tenuous Balance

Generali's leadership transition underscores the delicate balance between ESG-driven innovation and governance stability. While Caltagirone's legacy has embedded sustainability into the company's DNA, Delfin's challenge lies in ensuring these initiatives are executed cohesively. For investors, the path forward depends on whether Generali can reconcile its ESG ambitions with a governance model that fosters collaboration rather than conflict. Those willing to navigate this complexity may find opportunities in a company poised to lead in sustainable finance—if it can first resolve its internal fractures.