Jack Bailey


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Jack Bailey

Jack specialises in private wealth disputes, covering trusts and estates across the UK and including those involving international and offshore elements. Jack also regularly deals with disputes in the Court of Protection, particularly those relating to property and financial affairs.

Jack joined Stevens & Bolton in 2020 from a City firm and became a partner in 2024.

Jack works on a variety of trust and estate disputes including claims for breach of trust, the removal of trustees and executors, probate claims such as challenges to the validity of a will and claims under the Inheritance (Provision for Family and Dependants) Act 1975.

In the Court of Protection, Jack regularly advises on contentious applications such as disputed applications for authority to execute a statutory will or to authorise lifetime gifts as well as applications for the removal of a deputy or attorney.

Recent highlights include:

  • Acting in a claim concerning the estate of a high-profile figure seeking the removal of executors and, subsequently, the approval of a scheme for the distribution of the will trust
  • Acting in the estate of a high-profile figure in connection with the sum of £35m held in Natwest Bank since the 1940s
  • Acting in a claim concerning the estate of a high-profile figure in relation to chattels valued in the region of £15m, including the defence of claims relating to proprietary estoppel, mutual wills, contractual arrangements and will validity. Successfully achieving settlement before trial, including a significant costs concession from the opposing party
  • Advising the claimants/beneficiaries in relation to a breach of trust and related TOLATA application concerning a substantial country estate – working alongside the private wealth team to put forward an estate management scheme for approval by the Court on behalf of the trustees
  • Advising the defendant to a breach of trust claim in relation to a Cayman trust relating to assets in the UK and Belgium
  • Advising both claimants and defendants in numerous 1975 Act claims, regularly involving issues such as domicile and overseas assets
  • Acting for the professional deputy in an application in the Court of Protection for approval of historic general management costs, the judgment for which provided clarity on the circumstances in which professional deputies can seek assessed costs as opposed to fixed costs

Jack is listed as a “Star Associate” for private wealth disputes in Chambers HNW and as a “Rising Star” for contentious trusts and probate in The Legal 500. Jack is a member of ConTrA, the Contentious Trusts Association.

Jack has also been shortlisted for Lawyer of the Year – Senior/Managing Associate in the Citywealth Future Leaders Awards 2021.

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