Nothing is known for certain about this MP’s family background, although he was probably related to John Chaloner, an associate of Bartholomew Bolney*, the Lincoln’s inn lawyer, with whom he himself had close contact .
It seems likely that by the time Chaloner attested the Sussex elections of 1442 he had established himself as a landowner in the county, and he was living at Cuckfield by 1439.
Among those associated with Chaloner in this latter transaction was Bartholomew Bolney, with whom he had been linked in a professional capacity for many years, and who had already assisted him in his acquisition of land at Hurstpierpoint.
There is little to throw light on Chaloner’s political stance at this stage in his career. The Parliament had been summoned in the aftermath of the Yorkist victory at Northampton, but although Chaloner had been appointed to a royal commission back in 1455, shortly after the Yorkists had triumphed at St. Albans, no similar appointments were forthcoming when Edward IV came to the throne. It may be the case that at the time of his election he was already employed on the Sussex estates of the Mowbray dukes of Norfolk, for in the 1470s he served the then duke as under steward of courts in the barony of Lewes. He was retained in office when the Mowbray estates passed by marriage to the King’s younger son, Richard, duke of York. At the same time two of his kinsmen, both named John Chaloner, jointly occupied the parkership of Bentley in Cuckfield, which formed part of the same inheritance.
At an unknown date before November 1477, Chaloner relinquished to John Audley*, Lord Audley, his title to lands at Huntspill in Somerset, which, as they had once belonged to William Alberton, may have once pertained to his first wife.
