In a costs judgment handed down in July 2026, Mitch Winehouse was ordered to pay nearly £1 million in costs to two friends of his late daughter, Amy Winehouse. The judgment is a stark reminder that aggressive, bullying litigation tactics and speculative claims may lead to a substantial costs order rather than force a settlement. The case also confirms the continuing relevance of the established test for awarding indemnity costs.
Amy Winehouse died intestate in 2011. Her estate passed to her parents, and her father, Mitch Winehouse, was appointed its administrator. In 2021 and 2023, two of Amy’s close friends, Naomi Parry and Catriona Gourlay, auctioned around 140 of her personal items. Mitch brought proceedings alleging that Naomi and Catriona had no right to sell the items and that they had breached their fiduciary duties by concealing estate assets from him. In April 2026, the judge dismissed the claim, finding that the defendants had not deliberately concealed anything and that the items had either been loaned to Amy or gifted to them. The parties were unable to agree an order in respect of costs and the court has ordered Mitch to pay nearly £1 million of costs to Naomi and Catriona on the indemnity basis.
In litigation, the general rule is that the unsuccessful party will be ordered to pay the successful party’s costs, although the court may also make a different order after considering all the circumstances of the case. The court may also award costs on the indemnity basis, which is more favourable to the receiving party. When it comes to costs, the court’s discretion is broad, but an award to a successful defendant on the indemnity basis generally requires conduct or circumstances that take the case outside the “norm”. In exercising that discretion, the court may consider the unsuccessful claimant’s conduct before and during the proceedings, whether it was reasonable to bring and pursue the claims and allegations and the manner in which the case was conducted.
In Winehouse the judge justified awarding the defendants their costs on the indemnity basis for the following reasons:
- the persistence of the claim despite its weaknesses: the judge called the claim “speculative, weak, opportunistic and thin” and that it had been pleaded in vague and sloppy terms. The judge also criticised Mitch for pursuing a claim that had evidential difficulties and unreliable witnesses. His abandonment of some claims shortly before trial further indicated that he should have recognised sooner that parts of his case were unsustainable, and that his delay unnecessarily increased the defendants’ costs.
- the aggression: the judge found that Mitch and his solicitors tried to wear Naomi and Catriona down through aggressive and bullying litigation.
- the seriousness of the allegations and publicity: Mitch introduced serious allegations about Naomi and Catriona’s conduct which went beyond the dispute. He voiced these to the press and the judge found that this had damaged their reputations, career prospects, financial security and health.
- the approach to settlement: the judge was critical of Mitch’s position in relation to settlement and alternative dispute resolution, in particular how he refused to go ahead with a prearranged mediation and his unrealistic settlement position.
Although the Winehouse decision did not establish a new test for indemnity costs, it reaffirms that the court may exercise its broad discretion to award them where conduct or circumstances take a case outside the “norm”. Practitioners should bear in mind that robustly defending a claim does not, in itself, automatically result in an award on the indemnity basis; rather, the court may consider the cumulative effect of a party’s conduct throughout the proceedings.
The Winehouse case also highlights the need to review a case continually as proceedings develop. A claim that initially appears reasonable may become difficult to sustain after disclosure, witness evidence or other material emerges. Likewise, allegations against another party should be reassessed if they become unsupported, disproportionate or irrelevant. Practitioners should remember that litigation strategy therefore requires an ongoing review rather than being treated as a one-off decision made when proceedings are issued.
For practitioners, this principle has practical consequences throughout a claim. Clients should be advised not only about the steps they may take, but also about the potential costs consequences of taking them. Before making or maintaining a serious allegation, particularly one involving dishonesty, concealment or breach of duty, as in Winehouse, there should be clear and relevant evidence to support it. In the same way, where a claim or individual issue becomes difficult to sustain, practitioners should carefully consider maintaining it.
The practical lesson from Winehouse is therefore clear. It is not enough to ask whether a client can pursue a particular point, practitioners must also consider whether they should pursue it and whether it remains reasonable to do so as the litigation develops. The case demonstrates that an indemnity costs order does not necessarily result from one procedural misstep. Rather, the court may consider the overall course of conduct of a party and whether that conduct falls outside the ordinary and reasonable course of litigation. If so, the financial consequences for a party may be substantial.
About the author
Alexandra is a solicitor in the Wills & Trusts Disputes team at Wilsons Solicitors LLP, having joined Wilsons in September 2023. She graduated from the University of Southampton with a BA in English and then an MA in English Literary Studies. She then went on to study an MA in Law at the University of Law. Alexandra also holds a Master of Laws (LLM) in Professional Legal Practice. Alexandra completed her training contract with a Hampshire firm and qualified as a solicitor in May 2023. Alexandra advises on claims under the Inheritance (Provision for Family and Dependants) Act 1975, will validity, issues with executors, for both charities and private clients.Outside of work, Alexandra enjoys spending time with family, cooking, reading, and holidays in hot countries.
The views expressed in this article are those of the author and not necessarily those of Today’s Wills and Probate.
