Why “you should have pleaded differently” claims may fail early

This article was co-authored by Jack Orange, Trainee Solicitor.

In Powis Street Estates (No3) Ltd v Winston & Strawn London LLP [13.11.25], the High Court granted summary judgment in favour of leading counsel who was sued for alleged professional negligence in the conduct of earlier litigation. 

Whilst hindsight may be a wonderful thing, a claimant cannot use this to re-write history. The legal test is centred around what a reasonably competent practitioner would have done at the time. 

The Underlying Claim

The dispute originated in a property sale involving overage (an overage agreement is a type of contract where the seller will be paid extra by the buyer if the specified events happen within a specified timescale). The heads of terms referred to overage but did not specify a time limit, whereas the draft contract provided for a five-year overage period after exchange, resulting in the claimant receiving no overage payment.

The claimant property investment company subsequently brought a claim against those involved in the transaction and instructed solicitors who, in turn, instructed leading counsel to draft the particulars of claim. The case was pleaded on the basis that the five-year overage period had been included without the claimant’s instructions.

The claim later settled in 2023 for a total of over £1.9 million. 

The Negligence Claim

The claimant then pursued its legal team and, in particular, its barrister for professional negligence, alleging it should have recovered at least £3.6 million plus costs of c.£565,000. The claimant argued that leading counsel had failed to plead a different (and ‘better’) case, including allegations focused on the absence of a ‘best endeavours’ obligation to complete within five years and the risk of the five-year overage period running from exchange rather than completion.

The court rejected the claim at an early stage. The key point was not whether, with hindsight, an alternative pleading may have been available.  Instead, the claimant had to show a real prospect of proving that no reasonably competent barrister of counsel’s seniority would have failed to plead the ‘relevant claims’. The court held that the threshold was not met, particularly where the pleaded case was criticised as inadequately particularised and amounted to a hindsight critique. Whilst the claim against leading counsel has fallen away, the proceedings are currently progressing against the claimant’s instructing solicitor, Winston and Strawn London.

Comment

For professionals and their professional indemnity insurers, the decision is a useful authority in resisting conduct of litigation and ‘settlement regret’ claims, where they are, in reality, hindsight claims.

Furthermore, it reinforces that pleading and strategy choices are matters of professional judgement and a claimant must show that the approach taken fell outside the range of what a reasonably competent practitioner would have done; not simply that another alternative was possible and that with the benefit of hindsight, a claim could have been pleaded in a different way to secure a different settlement. 

The decision also emphasises that vague allegations are vulnerable if they are not particularly particularised and that the court will not look kindly on them. 

Finally, the decision also highlights the continuing importance of contemporaneous records of client instructions and the rationale for pleading decisions. Such contemporaneous records is what could save a professional, and in turn its professional indemnity insurers, when faced with a claim such as this.