Simon Raftopoulos is a partner and a member of the Corporate Finance and Private Equity teams. He represents clients in a wide variety of corporate finance transactions, including private equity and fund finance, joint ventures, mergers, acquisitions, leveraged buyouts, initial and secondary public offerings and private placements of equity and debt securities. Simon also represents clients on large private equity transactions and his team has a deep PE formation and transactional presence in Cayman.

Prior to joining Appleby, he was an associate in the Banking and Financial Services Group of Mathesons in Dublin.

Simon has consistently been ranked since 2012 and is highly rated globally across the leading legal directories. For 2019, he has been recognised by Who´s Who Legal as one of the world´s leading banking lawyers and ranked as a ´market leader´ in IFLR1000. Chambers Global described him as a “brilliant lawyer, with excellent and creative ideas for complex issues”. For 2018, he is a ´recommended´ lawyer in Legal 500 and described as “very technically sound, a problem-solver and extremely knowledgeable on Cayman law” in Chambers Global. Also in 2018, Simon has been recognised in the Merger & Acquisition chapter of Who’s Who Legal: M&A and Governance. He is quoted as earning his praise within the legal industry for his “precise and definitive” advice in Chambers Global 2016 and a “great banking lawyer who is extremely practical” in Chambers Global 2015. Legal 500 2015 reports that he is the “technically brilliant” global private equity head. Chambers Caribbean 2014 reported clients had this to say about Simon: “He provides really good service, and is very responsive and great when we need things done within a quick timeframe”.

Simon also participates regularly at conferences and seminars, and provides commentary to international and local media. He has been a contributing author to the Global Legal Insights Fund Finance publication since its inception. He also participated in the MandA.TV Leaderboard Interviews at the 2013 Cross Border M&A Advisor Symposium and spoke on the subject of ´Trends in Offshore M&A´. Simon also received the ´Finance Deal Maker of the year´ award in 2014.

Simon holds the Securities Institute International Capital Markets Qualification.

In the Cayman Islands, Simon has also been involved in undertaking pro bono charitable work at the Family Resource Centre.




Recent transactional highlights include:

  • Advising Fosun International in connection with the successful USD2.billion acquisition of Ironshore Insurance.
  • Advising Riverstone in connection with an initial public offering of the shares of Riverstone Energy Limited on the London Stock Exchange.
  • A leading upstream oil and gas focused private equity firm in successfully closing its US$3.5 billion fund.
  • The seller, as Cayman counsel, in connection with a US$1.9 billion acquisition of Central American banking firm BAC-Credomatic by Colombian banking conglomerate Grupo Aval (subject to regulatory approval and conditions).
  • The investors on the US$7.6 billion restructuring of the Education Media and Publishing group which was one of the largest of its type in Irish corporate history.
  • A leading offshore drill rig company and certain of its Cayman subsidiaries in the acquisition and/or transfer of drilling rigs, each valued at approximately half a billion US dollars.




Blackhall Place (Ireland)

University of Johannesburg (South Africa)

“[Simon] is always very responsive and gets things done in an organised and efficient process, so working with him is a real pleasure.”

Chambers Global


17 Jun 2019 | News

Appleby sponsors 5th annual European Fund Finance Symposium

Appleby is proud to be a platinum sponsor of the European Fund Finance Symposium, taking place in Lo...

19 Mar 2019 | News

Appleby sponsors 9th Global Fund Finance Symposium

Appleby continues to be a major contributor and platinum sponsor to the Global Fund Finance Associat...

Contributors: Anna-Lise Wisdom
10 Dec 2018 | News

Appleby Cayman advises on the take private AmTrust

Jacob MacAdam and Simon Raftopoulos, partners in Appleby’s Cayman Islands office, have advised on ...

Contributors: Simon Raftopoulos
19 Oct 2018 | News

Appleby proudly sponsors European Fund Finance Symposium

Founding member and annual platinum sponsor, Appleby, continues to be one of the major contributors ...

13 Mar 2018 | News

Appleby advises on major insurance transaction

Appleby advises longstanding client, Cunningham Lindsey, on its sale to Sedgwick Claims Management S...

Contributors: Simon Raftopoulos
22 Feb 2018 | Deals

Appleby advises Butterfield in connection with its acquisition of Deutsche Bank’s Global Trust Solutions business

Appleby (Cayman) Ltd. (Appleby) advised The Bank of N.T. Butterfield & Son Limited (Butterfield) in ...


Related People