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If the deal goes ahead it would boost Freshfields' corporate strength in the region as well as adding much-needed headcount.
Chiomenti terminated merger talks with US firm Shearman & Sterling earlier this year following "cultural differences". Sources close to the firm have confirmed that the Rome-based practice is in discussions with Freshfields.
Sources say that some of Freshfields' Italian lawyers had initially approached a group of Chiomenti's rainmakers with a view to cherry-picking particular partners. It is believed these local partners acted on their own initiative.
Those approached declined the offer to join Freshfields on this basis, but suggested a move towards a merger would be mutually advantageous.
A merger with Chiomenti would give Freshfields an edge in terms of critical mass, particularly in corporate and securitisation work. It would also give the firm territorial coverage that extends beyond highly competitive Milan.
Historically, Milan is Italy's legal centre, but growth is now coming from the privatisation opportunities provided by state-owned companies in Rome. In Milan there are 18 foreign practices compared with Rome's five, one of which is Freshfields' small three-partner office.
Chiomenti is essentially a Rome-based law firm, and a merger would put Freshfields in an ideal position to take greater advantage of the booming Rome market while at the same time boosting its Milan presence. Chiomenti also has a presence in Turin in the heart of the much ignored but highly lucrative northern belt which crosses from Turin to Venice.
Luigi Bendi, Chiomenti's senior partner and a member of the management committee, refuses to confirm that his firm is in talks with Freshfields, but does say: "We're always looking to come up with good Anglo-Saxon partners, and Freshfields is an extremely good firm in certain areas."
Freshfields managing partner Ian Terry would only compliment Chiomenti on being a "fine firm".
Chiomenti is believed to have terminated merger talks with Shearmans because the US firm was unable to provide what the Italians regarded as a realistic business plan that could cater or develop the needs of European clients. Chiomenti was concerned that Shearmans was too preoccupied with servicing its existing US clients in Italy to grow the Italian-based work effectively.
Shearmans is still hunting around the Italian market to find a suitable merger partner.
Freshfields is currently the only international magic circle firm not to have found a local Italian tie-up. Clifford Chance linked up with Grimaldi, Linklaters' alliance includes Gianni Origoni, and Allen & Overy merged with Brosio e Casati.