Loeb Smith Attorneys

Corporate / Investments Funds / Finance

Partner

Robert Farrell is a banking & finance lawyer and Partner in the Corporate, Funds & Finance Group at Loeb Smith Attorneys in the Cayman Islands. He specialises in cross-border financing transactions, investment fund finance, restructuring and special situations, advising lenders, borrowers and investment managers.

Before relocating offshore, Robert spent more than a decade practising as a banking & finance solicitor in England & Wales, advising banks, private credit institutions, private equity sponsors and corporate borrowers on a broad range of financing transactions across such sectors as healthcare, hospitality, real estate and infrastructure.

Clients value Robert for his ability to combine technical legal analysis with pragmatic commercial judgement, particularly on matters involving complex financing structures, distressed situations and evolving market practice.

As one client notes: “Robert Farrell is a brilliant professional whose dedication is at such a high level it feels as though he is part of our internal team.”

Robert’s recent work reflects the increasingly sophisticated nature of offshore banking & finance work. He routinely advises on debt finance arrangements involving international real estate assets, shipping finance and cross-border corporate lending structures. He also advises on regulatory issues arising in connection with financing transactions, including compliance with statutory “economic substance” obligations applicable to “finance and leasing” businesses and “banking” businesses.

Some recent and unique matters Robert has advised on include:

advising on a structured financing in connection with the acquisition of a Cayman Islands healthcare business, including the navigation of local business licensing requirements alongside the core transaction documents. The transaction also involved intricate intercreditor issues, as well as onshore tax considerations that influenced the group structure;

drafting loan, intercreditor and security documents in connection with the syndicated funding of the sale and transfer of participating shares in a Cayman Islands cryptocurrency hedge fund, which involved a bespoke security release mechanism. In addition to drafting the funding documents, Robert further advised on obtaining the investment manager’s consent to the creation of share security;

advising US- and UK-based investors on the restructuring of a Cayman Islands cryptocurrency trading SPV, including debt novation, debt forgiveness and debt-for-equity conversion to strengthen the company’s balance sheet;

advising a borrower client in connection with alleged events of default under loan arrangements denominated in digital assets, such as Bitcoin and USDT. The matter was complicated by the fact that Bitcoin was rallying significantly at the time, materially increasing the client’s economic exposure over the course of the dispute;

providing Cayman Islands expert evidence to the English High Court in cross-border bankruptcy proceedings involving a segregated portfolio structure and a disputed personal guarantee;

advising in connection with a complex cross-border fund finance matter arising from the disposal of a significant underlying asset by a Cayman Islands hedge fund, including the preparation of a detailed legal opinion for the auditors concerning the fund manager’s performance fee, distribution and clawback mechanics. The engagement required detailed analysis of valuation methodology, investor allocation rights and the interaction between the fund documentation, accounting treatment and the commercial allocation of financial risk;

structuring and launching a debt-focused master-feeder investment fund targeting opportunities within the entertainment industry, including financing arrangements backed by incomeproducing media rights and a new-to-market performance allocation structure; and

advising liquidators of a Cayman Islands company on creditor distributions and related collateral arrangements designed to protect against potential clawback exposure.

Alongside his transactional practice, Robert regularly advises on regulatory and governance issues affecting emerging technology and Web3 businesses. His work includes advising on tokenised investment funds, digital asset trading structures, financing arrangements involving crypto assets, as well as Cayman Islands and BVI regulatory perimeter issues.

Meanwhile, Robert has written extensively on the convergence of traditional finance and blockchain technology, particularly in the context of investment funds and fund finance structures. This reflects his broader practice focus on the evolving intersection between traditional financing structures and digital asset markets – placing him in a strong position to advise on matters that bridge conventional finance and emerging Web3 technologies.

Accolades 

Banking & Finance Expert of the Year in the Cayman Islands at The Lawyer Network Annual Awards 2026

Recent Articles

Why are Cayman Islands’ foundation companies popular? https://law.asia/cayman-islands-foundation-companies/

Cayman Court makes landmark decision in section 238 fair value dissenting merger/take-private case in Re Changyou.com Limited: https://www.loebsmith.com/legal/cayman-court-makes-landmark-decision-in-section-238-fair-value-dissenting-merger-take-private-case-in-re-changyou-com-limited-/341/

ESG In Finance Transactions and Investment Funds From An Offshore Law Perspective: https://www.loebsmith.com/legal/esg-in-finance-transactions-and-investment-funds-from-an-offshore-law-perspective/335/

Key Features and Benefits of a BVI Approved Fund: https://www.loebsmith.com/legal/key-features-and-benefits-of-a-bvi-approved-fund/343/

English

Cayman Islands Attorney

British Virgin Islands Attorney

Solicitor of the Supreme Court of England & Wales (non-practising)

Bachelor of Laws Degree (LLB Honours) – University of Leeds, England.

Postgraduate Diploma in Legal Practice – BPP Law School, Leeds, England

Real Estate Economics & Finance – London School of Economics

Financial Accounting - Harvard Business School

"Diligent, committed and hardworking...totally committed to a first-class service...[and] a high performer who pushes himself considerably".

Has a “can-do attitude that brings matters to conclusion swiftly and to the satisfaction of clients”.

Has a “sensible approach and gives me an informed view. He's just very easy to work with and has a good understanding of how I work”.

"Very impressive on the commercial finance side of transactions".

“Robert Farrell is a highly competent lawyer who’s easy going style belies his all-round experience and ability”.

“Praised for his ability to handle complex mandates”.