Henry Port, the father of Sir John, had been a mercer of Chester. He seems to have acquired some land in Etwall or had come to live with his son. In 1512 he died leaving a widow, Elizabeth, and their nine sons and eight daughters.
John became a lawyer, and married Jane, the daughter and heiress of John Fitzherbert of Etwall, who was the King's Remembrancer of the Exchequer. John Port was knighted in 1525 and became a Justice of the King's Bench two years later. He was one of the panel of judges at the trials of both Sir Thomas More and Queen Anne Boleyn, and after the dissolution of the monasteries he was able to acquire not only the land and buildings at Repton, but also the impropriate rectory of Etwall from Welbeck Abbey estates, and the Manor of Etwall from the Beauvale Priory estates. He and Jane had a family, and after her death he married Margaret, daughter of Sir Edward Trafford.
The family of Sir John Port was linked to the Harpur family (later of Calke*) through the marriage of Sir John's niece, Jane to Richard Harpur. Jane was the heiress of the Fyndernes, whose family had lived in the village of Findern, south of Derby, and from which they took their name. Richard Harpur had studied law. He rose to prominence in the profession and in 1567 was appointed a Justice of the Court of Common Pleas. At a time when property lawsuits were commonplace, he was in a position to earn a substantial income, and turned the experience he gained to his advantage. Through successful property dealings he was able to build up a considerable land holding, mainly in Staffordshire and Derbyshire. An estate in North Staffordshire, based on Alstonfield, was purchased, but considerable property in South Derbyshire, in the Trent valley, was acquired through his marriage.
* Henry Harpur, a grandson of Richard, bought Calke in 1622. At the turn of the nineteenth century Sir George Harpur changed the family name to Crewe. It changed again to Harpur-Crewe, when Charles Jenney inherited the estates from his aunt, Mrs. Moseley, in 1949. The family line came to an end in 1999 with the death of Airmyne, Charles' sister and, in 1981, heir.
When he died in 1557, Sir John Port provided in his will for the foundation of "Etwall Hospital", founded the same year:
"And also, I will, six of the poorest of Etwall Parish shall have weekly for ever twenty pence a-piece, over and besides such lodgings, as I, or my Executors, shall provide for them, in an Alms-house, which, God willing, shall be builded in or near to the Church yard at Etwall . . . "
The inmates were all to be men and were expected to observe a strict code of behaviour. For example, a list of regulations in 1687 declared that almsmen were to be expelled if they married. Well into the 20th century, the almsmen were bound to go to church daily, wearing their blue cloaks, silver badges and mortar-board type hats. Women became eligible for admission to Etwall Hospital in 1867.
Sir John's will also provided for a school to be set up in Etwall or Repton, to be taught by a priest. Although it was sited in Repton, for many years the Hospital was in charge of its administration. The two charities became a Corporation by a Royal Charter of 1622, which provided for the number of almsmen to be increased from six to twelve, because the value of the original endowments had greatly increased. It was only in the 19th century that the two charities went their separate ways. Richard Harpur and the three sons-in-law of Sir John Port became the hereditary Trustees of the Port Charity.
Sir John's son, also Sir John Port, must have been a very wealthy man indeed. Apart from the estates he had inherited from his father, he had married Elizabeth, the daughter and heiress of Sir Thomas Gifford of Chillington, whose wife was the co-heiress of the considerable Montgomery estates.