Practice Areas

01

Dispute Resolution

Simon is a dispute resolution solicitor specialising in complex, high-value disputes across commercial, corporate, and financial sectors. Acting for high-net-worth individuals, family offices, multinational companies, and sovereign investors, he brings strategic clarity to proceedings that often involve multiple jurisdictions and sensitive reputational considerations.

Drawing on extensive experience in cross-border litigation, arbitration, and negotiated settlements, Simon’s approach is defined by discretion, commercial acuity, and a deep understanding of the power dynamics that drive disputes. Clients value his ability to achieve resolutions without escalation – but with clear readiness to act decisively when litigation becomes necessary.

02

Corporate Disputes

Simon advises on contentious corporate matters including shareholder disputes, deadlock scenarios, breaches of directors’ duties, and contested exits. He is frequently instructed by founders, directors, institutional investors, and ultra-high-net-worth clients where control, strategy, or ownership is in question.

 

With a calm and commercially attuned approach, he is adept at managing disputes where the commercial viability of a business or the dynamics of a boardroom are under threat. Simon combines technical legal command with the ability to navigate power structures and sensitive personalities – often resolving matters discreetly while preserving long-term value.

03

Contractual Disputes

Simon represents clients in contractual disputes arising from complex commercial agreements, including claims for breach, misrepresentation, and failure of performance. His work spans sectors and jurisdictions, often involving bespoke or high-value contracts with significant commercial implications.

 

Acting for corporates, investors, and individuals, Simon brings forensic attention to contractual detail while keeping sight of the broader commercial context. His ability to identify strategic pressure points – whether through litigation, arbitration or private resolution – makes him a trusted advisor in situations where time, reputation, and commercial outcomes are critical.

04

White Collar Crime

Simon acts in serious and complex cases involving alleged fraud, bribery, money laundering, and other forms of corporate misconduct. His clients – ranging from senior executives and board members to corporate entities and professional advisors – rely on his ability to navigate parallel regulatory, criminal, and civil exposures.


With experience advising on internal investigations and representing clients in dealings with agencies such as the SFO, FCA and HMRC, Simon is known for his strategic judgment and discretion. He is particularly valued in situations where legal, reputational, and operational risks converge, and where clear, calm decision-making is paramount.

05

Tax Disputes

Simon advises on contentious tax matters including HMRC investigations, tax avoidance and evasion claims, structured tax arrangements, and cross-border liabilities. Acting for private clients, corporates, and fiduciaries, he provides strategic guidance from initial enquiries through to settlement or litigation, often working in coordination with leading tax counsel and advisors.


Simon’s cross-border experience, especially in relation to offshore structures and international tax regimes, allows him to manage disputes involving significant financial exposure and regulatory complexity. His approach is pragmatic and commercially focused – helping clients resolve disputes while protecting wider financial and reputational interests.

What Simon’s Clients Say

Simon is a first-class solicitor; he has tenacity and huge experience of criminal fraud cases, particularly bribery and competition cases, where he has a real expertise.
Legal 500
Simon assisted a client of mine with a very complex HMRC enquiry. His knowledge and experience were excellent. He communicated really well with the client and explained things in a way that were understandable to them, and most of all brought the long standing enquiry to a satisfactory close. It was a pleasure to work with him
Anna Goodship
Simon Caltagirone’s dynamic personality, litigation expertise and in-depth knowledge of the law, make him the first choice in selecting a solicitor. He is a master at strategising and devising creative solutions to complex legal challenges, particularly under pressure.
Corporate Client
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