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Mr. John McCaffery

Professional Description:

Chartered Accountant and Taxation Expert


FCA (ICAEW) Law Degree LLB Hons

Alexander & Co
17 St Ann's Square
M2 7PW
Area of work:



John McCaffery is tax partner and head of tax at Alexander & Co, having previously worked for two of the big four firms. 

Advising individuals, entrepreneurs, families and their businesses on tax issues and planning, John has particular expertise in transactional and forensic taxes.

John has engaged and advised on a wide variety of matters including matrimonial and shareholder disputes and arrangements, company and partnership acquisitions, disposals and reconstructions, structuring and advising on the tax consequences of investments by individuals including EIS and VCT arrangements, property planning and tax mitigation strategies. 

John has significant tax due diligence experience which involves detailed review of documentation, advising on and quantifying key tax exposures and developing potential solutions.

Main areas of specialisation include:

  • Tax on shareholder disputes
  • Tax on commercial litigation
  • Tax on matrimonial disputes
  • Tax on business acquisitions, reconstructions & disposals

Recent work includes:

Matrimonial/Shareholder Dispute: Joint expert advising on the separation of a property portfolio held within a corporate structure, where the parties were joint shareholders and required separation of the assets in a tax efficient manner.

Commercial / Shareholder Dispute: Expert witness for the defence, reporting on the application of the UK thin capitalisation and transfer pricing rules on a multi-million-pound international joint venture arrangement on the development of an African port operation through a UK Holding company.  As a direct result of this work the client obtained a multi-million pound settlement.

Legal Negligence: Expert witness for the defence reporting on the suitability of the sale and implementation of various tax avoidance schemes and VAT arrangements by a firm of accountants to a number of their clients via scheme providers.

HMRC Investigations: advising numerous clients on the tax consequences of various tax avoidance planning arrangements they had historically entered into, in light of the Advance Payment Notice and Follower Notice legislation recently introduced.

Shareholder Dispute: Reporting on the tax implications of the activities of a fraudulent managing director, advising on planning that would reduce the tax exposure to the company in relation to these activities and the removal of the director and managing this process with HMRC.

Matrimonial/Shareholder Dispute: Advising on the equitable separation of assets between divorcing parties where those assets included the disposal of a company, where both parties and their children where shareholders, A FURBS and other pension arrangements and several valuable properties held in complex structures.

Legal Negligence: Providing an expert opinion on the tax implications that arose from the solicitor’s client engaging in a scheme provided by a financial advisor that purported to allow the client to utilise his pension arrangements to fund his company via a sale and leaseback arrangement.  The client is in the process of litigating against the scheme provider and the case is in the process of being taken to the Tax Tribunal.

Commercial/Private Client: Advising and reporting on the tax implications of the acquisition of a business from an LLP that was owned by a corporate structure where the goodwill had been incorrectly separated from the main business.  This was followed by a refinancing of the business to increase the shareholding of the individual shareholders and undertake a partial exit of a trust shareholder.



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