To understand what is at stake behind the manoeuvres of recent years around Generali, you first need to grasp the figure of Francesco Gaetano Caltagirone. This Italian tycoon, whose fortune climbed to nearly €8bn in 2025 thanks to the performance of his construction group, Cementir, is not confined to the building sector. He also controls one of the country's most widely read daily newspapers as well as local titles, openly supportive of Giorgia Meloni's conservative government.
For years, he has wanted to get his hands on Generali, the insurance giant and a key player in Italian public financing. A strategic takeover would directly serve his industrial interests, since the insurer is a leading investor in Italian real estate. But without the wealth required to launch a takeover bid, Caltagirone is pursuing another route: taking power from within.
A war of influence inside the boardroom
For several years, he has worked to gain control of the board by putting forward his own slates of directors, in opposition to outgoing CEO Philippe Donnet. In 2025, Donnet was again reappointed thanks to the backing of Mediobanca, Generali's largest shareholder with a 13% stake. Foreign investment funds tipped the balance, well aware that a potential politicisation of the group would not bode well for shareholders.
Although it may already be too late. Philippe Donnet and Natixis were forced to abandon their plan to combine their asset-management businesses, which could have created a European giant managing around €1,900bn. The Italian government had firmly opposed the move over fears of losing control of Italians' savings-widely invested in domestic bonds.
An alliance game
Caltagirone can rely on a strategic alliance with the Del Vecchio family. Above all Leonardo, who died a few years ago and founded Luxottica. His legacy lives on through the family holding company, Delfin, led by Francesco Milleri, who is also CEO of EssilorLuxottica.
Together, they hold 17% of Generali. This duo also controls close to one-third of Banca Monte dei Paschi di Siena (MPS), which has just taken control… of Mediobanca.
The alliance game becomes clear. By establishing themselves at MPS, both men would push aside Philippe Donnet's main supporter, paving the way for a knock-on takeover of Generali. Caltagirone and his allies now hold one-third of the insurer's capital.
Meloni, bystander or beneficiary?
For Giorgia Meloni, this reshaping of financial power is not trivial. The Financial Times recalls the scars left by her time in Berlusconi's government, at the height of the euro zone crisis. Even today, she wants Italian debt to remain in the hands of domestic investors, to limit the risk of capital flight.
Having an ally at the helm of Generali, one of the largest buyers of government bonds, would be a boon. She has made a point of prioritising the clean-up of public spending during her term.
Spread between German and Italian bonds (Source: TradingView)
Giorgia Meloni became prime minister on 22 October 2022.
Cooperation between Caltagirone and Meloni could increase the insurer's commitment to holding Italian sovereign bonds.
A plan too perfect?
While Francesco Caltagirone has never been so close to finally ousting Generali's CEO and installing one of his own, headwinds have emerged and threaten to bring this elegant plan to an end.
First, a judicial investigation is now targeting Caltagirone, MPS CEO Luigi Lovaglio, and Francesco Milleri. The allegations concern collusion in the takeover of Mediobanca.
Damning wiretaps are fuelling those suspicions. The Financial Times reports that in one of them, Lovaglio told Caltagirone: "You were the real engineer, I only carried out the mission…You cooked up something perfect, so congratulations on that idea”.
The other threat lies in Leonardo Del Vecchio's holdings outside EssilorLuxottica. Francesco Milleri is seeking buyers, and UniCredit has been cited in the media this week as a potential acquirer.
The legal case involving some members of the holding company is very likely linked to that intention, Alphavalue notes.
Despite the headwinds, the Financial Times says that even the most ardent defenders of Generali's independence admit Caltagirone could end up prevailing. Not by force, but through patient influence in the boardroom.
