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One of Generali's major investors is contemplating contesting the reappointment of long-serving CEO Philippe Donnet in May. The investor is exploring other potential candidates to lead Italy's largest insurer, according to four sources familiar with the situation.

Three years ago, Francesco Gaetano Caltagirone, holding a 6.9% stake in Generali, spearheaded an unsuccessful bid to replace Donnet, who had the support of the insurer's board and its primary shareholder Mediobanca.

Caltagirone, along with the late billionaire Leonardo Del Vecchio, has criticized Donnet for his alleged failure to sufficiently expand Generali during his tenure since 2016.

More recently, these two investors have raised concerns about a proposed asset management collaboration between Generali and France's BPCE, citing apprehensions about the potential influence from the French side in the partnership.

Caltagirone has yet to finalize his strategy for the shareholder vote on May 8 to appoint a new Generali board and may even choose not to nominate a new CEO candidate, as per one of the sources.

However, he is contemplating suggesting alternative candidates, including current Enel CEO Flavio Cattaneo, who became a Generali director in 2022 under Caltagirone's representation, as reported by three sources to Reuters.

Cattaneo is likely to be nominated again by Caltagirone as a director. Nevertheless, proposing him for the CEO position could pose challenges given his existing responsibilities at Enel.

A spokesperson for Enel clarified that Cattaneo's current mandate at Enel extends until 2026, stating, therefore the Enel CEO is not free to assume other roles.

According to the sources, there are similar concerns about two other candidates under Caltagirone's consideration.

Caltagirone has strong ties with Matteo Del Fante, the CEO of the national postal service Poste Italiane, and Fabrizio Palermo, the CEO of Rome utility Acea. He is contemplating either of them as a potential successor to Donnet.

Representatives for Poste and Caltagirone declined to provide comments. A spokesperson for Acea mentioned that Palermo's term expires in 2026 and he is focused on the company's business plan.

Donnet has expressed willingness to serve another term, but this time, he is not being endorsed by Generali's board due to new regulations from Italy's government, which make it challenging for an outgoing board to propose candidates.

Amidst these uncertainties in Generali's leadership, top shareholder Mediobanca is facing a hostile takeover attempt by Monte dei Paschi di Siena (MPS), a state-backed bank in which Caltagirone has acquired a stake since November.

On January 28, Mediobanca highlighted the interlocking ownership stakes among MPS, Generali, and Mediobanca.

Caltagirone and the heirs of Del Vecchio collectively own 17% of Generali, 27% of Mediobanca, and 15% of MPS.

Three years ago, Caltagirone and Del Vecchio suffered a defeat in a shareholder vote after nominating former Generali executive Luciano Cirina as their CEO contender.

UniCredit recently made a surprising move that could influence the potential conflict between Mediobanca and Caltagirone regarding Generali.