Pan's name is often misspelt as Payn in the belief that he was a Jerseyman, but Pen was from England and he was appointed Bailiff for a short period, replacing Jean Lempriere ( -1534) and Richard Mabon as substitute for Helier De Carteret who was under suspension for the second time in his career. Nothing is on record of Pen's background and how he came to be appointed Bailiff. It is assumed that he was an associate of the Governor, Sir Hugh Vaughan.
De Carteret sometimes made surprise visits to Jersey, and during one of these Pen tried to assassinate him in the Market Place, resulting in a fight with drawn swords.
De Carteret was suspended for two years between 1514 and 1516 and again from 1516 to 1523, as a result of a long-running battle with the Sir Hugh Vaughan, and for three years at the start of the second suspension, Jerseymen Jurat Jean Lempriere and the Dean, Richard Mabon, were appointed jointly to carry out his responsibilities. It is thought that King Henry VII's court then decided to indicate who had ultimate control over the island by replacing them with Pen, an Englishman.
However, Pen must have had an earlier involvement in the island's administration because on 15 December 1523, just after de Carteret's second suspension started, records show that he was given a licence "to import 300 tons of bay salt of France into the islands of Jernesey and Garnesey", and to export merchandise thence to France. (Del. Hampton Court, 15 Dec. 15 Hen. VIII.—S.B. Fr. m. 5.). Pen is not shown as a lieutenant to Vaughan, so it is possible that he was acting as Bailiff at that time, or simply involved in private trade between the island and France.
When Helier de Carteret finally won his legal action against Sir Hugh Vaughan and was reinstated as Bailiff, Pen, along with the other temporary appointments made by Sir Hugh, was found to have held office illegally and had to reimburse de Carteret with all payments he received while acting as Bailiff.