(i) Whether loss caused by a breach of constructive trust is compensatable in principle.
The constructive trust was equity’s response to the breach that generated the unauthorised profits, giving Hotel Portfolio II an immediate proprietary interest in the fund representing those profits. The Supreme Court's view was that it would be "extraordinary and contrary to basic equitable principle for the dissipation of a fund held on an institutional constructive trust to give rise to no remedy by way of equitable compensation for any consequential loss".
(ii) Whether Hotel Portfolio II suffered a loss as a result of the dissipation.
The assessment of equitable compensation for breaches of trust is to be conducted through a “but-for” counterfactual: what would have been the beneficiary’s position but for the breach of trust?
Mr Stevens argued that Hotel Portfolio II had suffered no real loss because the dissipation breach was aggregated with the earlier breach that generated the profits and, therefore, Hotel Portfolio II was in the equivalent position to that in which neither breach had occurred. The Supreme Court disagreed. It found that this argument did not follow the case law, was inconsistent with the purpose of the constructive trust, and would enable "the dishonest assistant to escape scot-free". Instead of a counterfactual where the constructive trust never came into being, the correct counterfactual was one where the trust fund had not been dissipated. Therefore, Hotel Portfolio II had suffered loss in the full amount of £103.76 million.
(iii) If so, whether the profits from the onwards sale could be treated as a gain made for the benefit of Hotel Portfolio II and set off against the subsequent dissipation loss to reduce Mr Stevens’ liability.
The general rule is that a trustee is not permitted to set off gains made in one breach of trust against losses made in another. There is, however, a permitted exception where breaches arise in the same transaction and a strict application of the rule would lead to a plainly inequitable result. Mr Stevens argued that the transactions were all connected in such a way that the exception should apply. The Supreme Court were unpersuaded, describing his argument as "fantastical".