Citywealth Leaders List, 60 second interview – Alessia Allegretti, Boies Schiller Flexner

Date: 20 Jan 2026

Karen Jones

This week’s 60 seconds Citywealth Leaders List interview is dedicated to Alessia Allegretti, Founding Partner and Co-Managing Partner, Milan and Rome, at Boies Schiller Flexner.

Picture of Alessia Allegretti, Boies Schiller Flexner
Alessia Allegretti, Boies Schiller Flexner

Tell CityWealth readers a bit about your role.

I am a partner at Boies Schiller Flexner, a US law firm, based in Italy. I advise companies, entrepreneurs and families with international interests on cross-border corporate, governance and strategic structuring matters. My practice sits at the intersection of business and private client advisory, and I often work on situations where ownership, succession, governance and international structuring overlap.

What does a typical day look like for you?

There is no real “typical” day, which is one of the aspects of my work I enjoy most.

My time is usually divided between client calls across different jurisdictions, internal coordination and decision-making, and broader management and business development responsibilities. Whenever possible, I make a point of spending time with clients within their companies, as understanding how their businesses actually function – and how decisions are taken in practice – is essential to anticipating their needs, building long-term, trust-based relationships, and providing effective advice.

Tell us about some recent, interesting client instructions or requests you have received.

Over the past year, I have been involved in several particularly complex and sensitive matters. One of these concerned advising a single family office in connection with criminal and tax litigation in Italy relating to a superyacht, a highly delicate situation requiring careful coordination of legal strategy.

I am also currently involved in a tense succession handover from father to son concerning the father’s 49 per cent stake in a business he founded. The situation is further complicated by the fact that the remaining 51 per cent is held by a UK-based private equity fund, creating a challenging interplay between family dynamics, governance considerations and third-party investor interests, all of which require a measured and pragmatic approach.

In addition, I have been working on a contentious trust dispute in New Zealand, assisting the Italian settlor in connection with breaches of fiduciary duties by the trustees. The matter has required close coordination across jurisdictions and a strategic approach to managing legal, tax and relational complexities.

What challenges do your clients face and how are you helping your clients to overcome them?

One of the main challenges my clients face is managing complexity across borders. Assets, businesses and family members are often spread across multiple jurisdictions, and decisions taken in one area can have unintended consequences elsewhere. I support clients by providing a clear strategic framework, acting as a trusted advisor throughout the process, and ensuring that the various interests at stake are properly aligned.

What is your proudest professional achievement?

My proudest professional achievement is probably having worked alongside David Boies and my long-standing partner Luigi Macioce to establish the Italian operations of Boies Schiller Flexner and, in four years, fully integrate the Italian office into the firm’s US platform. David is a legendary lawyer and, beyond that, a very special person. Being trusted to help build the firm’s presence in Italy and to contribute to its integration at a global level has been both professionally and personally significant.

More broadly, I am proud of the many long-term personal relationships I have built with clients over the years.

What do you consider to be the most important attributes for a leader?

Determination, clarity and consistency are fundamental, together with ethics and a great deal of responsibility. Above all, a leader needs a clear vision and the ability to translate that vision into decisions that inspire trust and provide direction, especially in complex or uncertain situations.

 Who do you most admire and why?

I tend to admire people who combine technical excellence with integrity and a strong sense of responsibility.

Where was the last place you travelled to for work or pleasure?

I travelled to Panama and the San Blas Islands from 28 December to 6 January, which was a wonderful way to start the new year. All the ingredients for a perfect holiday were there: a blend of striking, powerful nature, warm and smiling people, great food and Latin music.

If you were not in this industry, what else might you be doing?

If I were not working in law, I would likely be involved in luxury travel. I enjoy curating experiences, discovering different places and cultures, and understanding what makes a journey truly distinctive, which, in a way, is not so different from what I do professionally.

How do you relax after a long day?

I usually relax at home with my partner and, when possible, by returning to my native village in Valle d’Aosta to see my two little nephews. Being around them is a great way to reset and gain perspective after intense days.

If you could recommend one person in the private wealth industry, who would it be and what would you say about them?

I would mention the same professionals I have already referred to in my submission:

Luigi Macioce, partner at Boies Schiller Flexner, who is qualified both as a lawyer and a tax advisor and combines the two perspectives in an integrated and highly pragmatic way on complex cross-border matters.

Maria De Peverelli at Stonehage Fleming Family Office, an art expert with deep experience in advising families on the management and long-term stewardship of significant art collections.

Raffaella Sarro at La Trust Company, a professional trustee with extensive experience in trust structuring and administration.


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