On his election to the abbacy Samson took steps to remedy his lack of the legal knowledge necessary in his new office for the protection of St Edmunds’ liberties and possessions. He appointed men learned in secular law to advise and instruct him – Jocelin refers to them as his ‘private counsellors’ – and studied appropriate legal texts. Thus, he soon became a formidable party in the law courts and was regarded as a wise judge. At some stage he was appointed a royal justice in eyre (but is known to have served only once, that was on a circuit in September and October 1194, in Norfolk, Suffolk, Cambridgeshire, Essex, Hertfordshire and Huntingdonshire).

Excellent illustrations of the legal skill of Samson and his lawyers are in Jocelin's chronicle and in the Public Records. Thus, Jocelin relates, the merchants of London desired to be quit of toll in the Bury market, but many nevertheless grudgingly paid it. The citizens of London on this account made a ‘great commotion’ in their hustings court and sent messengers to Samson informing him that by virtue of a charter of Henry II, Londoners were exempt from toll throughout England. Samson replied that he called the king to warrant that the king had never given them any charter to the prejudice of St Edmunds’ liberties, which were granted before the Conquest by Edward the Confessor; furthermore, although the king could grant quittance from toll throughout his own dominions, he could not do so in the town of Bury St Edmunds since within the banleuca where the market was situated, the abbot enjoyed regalian rights. The Londoners persisted in the dispute with bitter acrimony and threats of violence. Worst of all, they boycotted the Bury market for two years, ‘from which our market suffered great loss, and oblations received by the sacrist were greatly diminished.’ So the quarrel dragged on until Samson compromised and persuaded the Londoners to await the king's return so that he might take his advice. Jocelin does not date this episode, but possibly the king in question was Richard I who returned from captivity in Germany in March 1194.