It is possible that Chiksond was a relative of Nicholas ‘Chekesand’, who obtained seisin of a messuage in St. Ives, Huntingdonshire, in 1415. He is first heard of in June 1426, when the Huntingdon wool merchant, John Colles*, gave up his right to land at St. Ives they had hitherto held jointly.
At the end of the 1420s, Chiksond became one of the bailiffs of Huntingdon, an office in which he was to serve no fewer than six terms, some of them consecutive. Administratively speaking, the following decade was probably the busiest decade of his life. He sat in the Parliaments of 1431 and 1435, the second of which coincided with one of his terms as bailiff and, after leaving the latter assembly, he became coroner of Huntingdon. Undoubtedly one of the leading residents of the town by this stage in his career, he swore the oath to keep the peace administered throughout the country in May 1434.
Earlier in the same decade, Chiksond fell out with his erstwhile associate, John Colles. In about 1432 Colles sued him and John Andrew II* for breach of trust, claiming that they had refused to return lands in Hartford near Huntingdon, which he had entrusted to their care before going overseas.
The next evidence of Chiksond is from the later 1440s, when he attested the return of Huntingdon’s burgesses to three consecutive Parliaments. He also took part in the controversial Huntingdonshire county election of 1450, as one of the ‘gentlemen’ who supported the return of Robert Stonham* and John Styuecle*. It is unlikely that he was usually styled as such (in 1462, for example, he was a ‘yeoman’),
