The full extent of Bailey’s landholdings was not made clear in the earlier biography,
Bailey’s association with the Montagu earls of Salisbury dated back to the days of Earl John at the end of the fourteenth century, when he was serving as constable of the comital castle of Christchurch in Hampshire. Following the earl’s attainder and execution, he was replaced in this office by the royal nominee Thomas Gerard.
It was, however, the death at the siege of Orléans of Thomas Montagu, earl of Salisbury, without legitimate male issue that was to cause protracted troubles for his executors and feoffees, Bailey among them. Apart from the heirs general, Richard Neville and his wife Alice Montagu, the new earl and countess of Salisbury, Earl Thomas’s cousin William Montagu* also staked his claim to some of the estates of the earldom in the Westminster law courts. It seems that Bailey rapidly came to terms with the Nevilles, to whom he released his title before the end of 1429.
