The Billionaire Who Would Revive Generali by Preventing a Deal

The apartment blocks which Francesco Gaetano Caltagirone has constructed across Rome since the 1960s are so ubiquitous, the construction tycoon is sometimes referred to as the city’s “Eighth King.”

Now, the 82-year-old ruler of a corporate empire stretching from cement to newspapers, banks and insurance companies is engaged in a boardroom struggle that is set to shape the future of Italian finance — and define his own legacy.

The real estate billionaire, who holds the third-largest stake in Italy’s biggest insurer, Assicurazioni Generali SpA, is opposed to a partnership deal that Generali’s CEO, Philippe Donnet, wants to make with the owners ...