Simon Raftopoulos

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T +1 345 814 2748

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Simon Raftopoulos is the Local Corporate Practice Group Head in the Cayman Islands 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. He is currently recognised by Who´s Who Legal 2021 as one of the world´s leading banking and M&A lawyers, a ´market leader´ in IFLR1000’s 2020 rankings as well as ranked as a 2020 ‘leading individual’ in Legal 500. Chambers Global reported that clients laud him for his skills and describe him as “commercial and practical [with] a good group of lawyers around him”. Past Chambers Global directories have described him as a “brilliant lawyer, with excellent and creative ideas for complex issues”. In 2019 he was ranked as a ‘leading individual’ and in 2018, he was a ´recommended´ lawyer in Legal 500 described as “very technically sound, a problem-solver” and “extremely knowledgeable on Cayman law” in Chambers Global. Also in 2018, Simon was 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 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 undertaken pro bono work for over a decade and is a recipient of the Lee Friedman award for his service to the Family Crisis Centre and the community.


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


13 Sep 2021

Cayman Private Fund Annual Return and Related Fund Entity Deadlines Extended (Final Extension)

The Cayman Islands Monetary Authority issued a notice on 10 September 2021 advising that the filing ...

24 Aug 2021

The filing deadline for private funds annual return is coming soon – are you ready?

As part of their ongoing regulatory reporting requirements, CIMA registered private funds establishe...

14 Jul 2021 | News

Recent updates of the Cayman Islands Economic Substance Regime bring certain Partnerships into scope

On 30 June 2021, the Cayman Islands Government gazetted an amendment of the ES Schedule Regulations ...

14 May 2020 | News

Anti-takeover strategies during COVID-19

The unprecedented market volatility and substantial declines in stock prices that we have witnessed ...

29 Apr 2020 | Analysis

COVID-19 Merger and Acquisition Update

In these uncertain times we have had numerous enquiries from clients as to what we think is going to...

23 Apr 2020 | News

Corporate Governance during COVID-19

In each of Appleby’s jurisdictions, measures have been taken to combat the spread of COVID-19. Wh...

16 Mar 2020 | News

Appleby announces new Office Managing Partner in Cayman

Leading law firm Appleby has announced a number of high profile internal appointments to further str...


7 Oct 2021 |

Regulatory Round-Up: Cayman Islands Q3 2021

Appleby Cayman’s Our latest Regulatory updates for the Cayman Islands up to Q3 2021.

27 Jan 2021 |

Appleby contributes four chapters to Global Legal Insights – Fund Finance 2021: Cayman Islands

The subscription credit and fund finance markets have remained relatively robust over the course of ...

Contributors: Anna-Lise Wisdom
31 Dec 2020 |

Cayman Regulatory Newsletter Q4 2020

Appleby Cayman’s third quarterly publication of the year focuses on regulatory developments, inclu...

Contributors: Peter Colegate
30 Sep 2020 |

Cayman Regulatory Newsletter Q3 2020

Appleby Cayman’s third quarterly publication of the year focuses on regulatory developments, inclu...

Contributors: Peter Colegate
29 Jun 2020 |

Cayman Regulatory Newsletter Q2 2020

Appleby Cayman’s second quarterly publication of the year focuses on regulatory developments, incl...

17 Mar 2020 |

Cayman Regulatory Newsletter Q1 2020

Appleby Cayman’s first quarterly publication of the year focuses on the topics making waves now, i...

13 Mar 2020 |

Appleby contributes five chapters to Global Legal Insights – Fund Finance 2020

Appleby provided five chapters to the Global Legal Insights - Fund Finance 2020 Guide. The publicati...

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