Department profile
Appleby

Corporate & Finance

Global Guide 2026 : Cayman Islands


Appleby

Rankings

About

Provided by Appleby

In the corporate finance space, our team advise on a full spectrum of acquisition and leveraged financing, loan financing and bespoke structures, including mergers and acquisitions, public to private deals, corporate finance and restructurings. Clients include all major banks, public companies and financial institutions. We also continue to dominate the fund finance lending space, particularly in subscription finance. In the structured finance market, our practice includes over a third of the CLO market handling not only a large number of new issuance CLOS but also refinancing and re-set transactions; representing premier managers and all the major underwriters. Our corporate restructuring team act as both company counsel and for creditors and creditor committees, applying expert knowledge and experience and assisting clients with situations involving financially distressed companies; using both Cayman and US restructuring tools. Our teams also has an in-depth knowledge and are leaders in Cayman cross-border mergers and acquisitions and has a market leading equity capital markets practice, handling many of the biggest and complex transactions in recent years. We also advise our clients with regard to regulatory matters including compliance.
Alerts to clients on the introduction of new regulations and changes to the law which affect their business are delivered regularly by our team.

Chambers Review

Provided by Chambers

Corporate & Finance - Cayman Islands

Band 1

Band 1


What the Team is Known For

Appleby has a market-leading finance practice acting for an impressive list of financial institutions. The law firm regularly represents underwriters in structured finance transactions, including CLOs. It possesses further strengths in fund finance, as well as debt capital markets and derivatives issuances. The firm's finance expertise is complemented by a sound understanding of M&A and regulatory issues.

Work Highlights

Provided by Chambers

  • Appleby was Cayman counsel to JetBlue Airways, and its subsidiaries, on a USD2.75 billion debt issuance backed by the airline's loyalty programme.

Strengths

Provided by Chambers

  • Appleby's team is responsive, technically strong and always very helpful.

    Corporate & Finance respondentGlobal
  • Appleby understands clients' goals and risk appetite, and addresses issues and advice accordingly.

    Corporate & Finance respondentGlobal
  • Appleby always takes a very commercial approach and is thoughtful about flagging the nuances to us.

    Corporate & Finance respondentGlobal
  • Appleby’s Cayman team is technically strong, highly responsive and commercially focused. It consistently delivers clear, actionable advice, particularly on complex regulatory and governance matters.

    Corporate & Finance respondentGlobal
  • One of the main reasons I consistently turn to Appleby is because it is considerate of all variables in a deal and highly attentive to the client's approach and goals.

    Corporate & Finance respondentGlobal

Notable Practitioners

Provided by Chambers

  • Band 1Benjamin Woolf
    Band 1Benjamin Woolf

    Benjamin Woolf

    Benjamin Woolf comes highly recommended for his strengths in Cayman structured finance mandates, particularly CLOs. He is also very capable when it comes to mergers, acquisitions and debt capital markets issuances.
    • Benjamin Woolf is an excellent and reliable lawyer.

      Corporate & Finance respondentGlobal
  • Band 1Simon Raftopoulos
    Band 1Simon Raftopoulos

    Simon Raftopoulos

    Simon Raftopoulos is a well-established figure in the Cayman Islands and leads Appleby's corporate team within the jurisdiction. He is also extremely experienced in equity finance as well as fund finance, with regular roles advising financial institutions on their provision of credit to private equity funds and related entities such as investment advisers.
    • Simon Raftopoulos is easy to work with and I feel I can be direct with him about everything.

      Corporate & Finance respondentGlobal
    • Simon Raftopoulos is a longstanding leader in the fund finance space.

      Corporate & Finance respondentGlobal
    • Simon is my go-to Cayman partner. I trust him to guide us on legal issues and help us meet our clients' expectations. He is extremely available and attentive.

      Corporate & Finance respondentGlobal
    • Simon Raftopoulos is a very smart and experienced lawyer. We are happy to have him as a part of our team.

      Corporate & Finance respondentGlobal
  • Band 3Caroline Barton
    Band 3Caroline Barton

    Caroline Barton

    Caroline Barton heads Appleby's banking and asset finance group, in which position she has significant experience advising borrowers as well as lenders. In addition to finance work she is also well accustomed to advising on capital markets transactions, including the issuance of American depositary shares.
    • Caroline Barton is efficient, to the point and replies quickly.

      Corporate & Finance respondentGlobal
  • Band 3Jacob MacAdam
    Band 3Jacob MacAdam

    Jacob MacAdam

    Jacob MacAdam advises international banks, corporate clients and private equity firms on a variety of financing arrangements, M&A and capital markets activities, as well as corporate restructurings.
    • Jacob MacAdam is a huge asset to our advisory group. He is a thought leader in the field and has presented options few other legal advisers would have considered.

      Corporate & Finance respondentGlobal
    • I can confidently say he is exceptional in every respect. His technical knowledge and precision are outstanding, with every piece of advice being clear, thorough and strategically sound.

      Corporate & Finance respondentGlobal
    • Jacob MacAdam is a fantastic business lawyer. He knows what matters and how to get a deal done.

      Corporate & Finance respondentGlobal

Ranked Individuals at Appleby (4)

Cayman Islands

Members

Provided by Appleby

Appleby has rankings in the following guides

What success is built on

Chambers is the leading data and intelligence partner for the legal sector.

Explore thought leadership