The Mediobanca-Generali Deal: A Crossroads of Stakeholder Power and Strategic Risk

Let me tell you, the Mediobanca-Generali deal is a high-stakes game of corporate chess. With the shareholder vote delayed until September 25, 2025, this is a critical moment for investors to assess whether the complex web of cross-holdings and shareholder politics can be untangled in time—or if this deal is heading for a disastrous stalemate.

The Stakes: A Delayed Vote and a Hostile Bid Looming
Mediobanca's postponement of its shareholder vote isn't just a bump in the road—it's a red flag. The original June 16 deadline was scrapped because major players like the Del Vecchio and Benetton families, UniCredit, and Francesco Gaetano Caltagirone (who collectively hold over 34% of Mediobanca's shares) are withholding support until Assicurazioni Generali (AG) clarifies its position. AG holds 50% of Banca Generali, making its approval essential. But here's the rub: AG only began evaluating the deal on June 12, 2025—leaving just three months to align interests before the September vote.

Notice how shares have already dipped 2.1% since the postponement was announced? That's investor skepticism screaming, “This deal is far from done.”

The Cross-Holdings Quagmire: Why Everyone's a Foe (or a Friend?)
This isn't just about Mediobanca buying Banca Generali. It's about dismantling Italy's Byzantine web of cross-shareholdings. Mediobanca is offering its 13% stake in AG to acquire Banca Generali—a move that would reduce its exposure to AG while boosting private wealth management. But here's the problem:

• Del Vecchio (20% Mediobanca stake): His Delfin Group is a major AG shareholder. If AG isn't getting a better deal, he'll block the vote.
• Benetton (2.2% Mediobanca stake): They're cross-invested too. Their support hinges on AG's terms.
• Caltagirone (10% Mediobanca stake): He's outright opposed, fearing the deal dilutes Mediobanca's value.

Add in UniCredit's 1.9% stake, which it might abstain, and you've got a bloc that could kill this deal. The Bloomberg report warning of over 40% opposition/abstentions isn't a scare tactic—it's math.

Monte Paschi's Shadow: The Hostile Bid Threat
Mediobanca's CEO, Alberto Nagel, isn't just playing defense here—he's in full panic mode. Why? Because state-backed Banca Monte dei Paschi di Siena (MPS) is itching to launch a hostile bid. Nagel's strategy is to grow Mediobanca too big for MPS to swallow—but if the Banca Generali deal fails, MPS pounces.

Look at MPS's shares—up 8% this year. They're positioning for a fight. Mediobanca's projected 20% ROE (up from 14%) and €300M synergies are compelling, but they're meaningless if the deal collapses.

Market Skepticism: A Vote of No Confidence
Investors are already voting with their wallets. AG's shares fell 1.2% post-postponement, and Banca Generali's dropped 2.1%. Why? Because the market sees two glaring risks:

1. Time is Running Out: AG needs to deliver a “yes” by early September, or the vote fails. No time for dithering.
2. Strategic Gaps: Even if the deal passes, AG's divestment of Banca Generali means it loses a revenue stream. Without new partnerships, AG's valuation could crater.

Investment Advice: Wait-and-See Until September 25
Here's my take: This deal is a gamble with too many loaded dice. The risks—Monte Paschi's bid, shareholder defections, and cross-holdings chaos—outweigh the rewards unless there's a last-minute breakthrough.

• Hold Off on Buying: Mediobanca's stock is already down on uncertainty. Wait until after the vote to see if Nagel can rally support.
• Watch AG's Moves: If AG and Mediobanca can't agree on commercial partnerships by August, sell the dip.
• Beware Monte Paschi: If the deal fails, MPS's bid could send Mediobanca's shares soaring—but that's a high-risk bet.

The bottom line? This is a “sit on your hands” situation until September 25. The cross-holdings mess and shareholder infighting make this a landmine field, not an investment playground. Don't get crushed by the crossfire.

Final Call: Hold cash here. Let the dust settle.