In the closing months of 1481, Richard Cely, an English wool merchant, and his eldest son, Richard the younger, were indicted for poaching a hart and two calves in the royal forest near Dartford in Kent. The pair of men, naturally anxious to avoid facing the charges in court, found an ally of social and political standing in Sir Thomas Montgomery. It was the Celys’ hope that Montgomery would exert his influence on their behalf to shield them from the law. After receiving word that the knight had crossed the Channel to Calais, Richard the younger wrote to his brother, George, who was stationed there. He urged his sibling to ‘whate apon hym and thanke hym for us for he has beyn howr spessyall good master in thys mater … thorrow hys labor I am cwm in qwatans of dyvars whowrschypfull men that wyll myche for ws for hys sake’. This assurance of good lordship had been purchased with a gift of £5 and ‘whalew of a pype whyn’ for Montgomery and a payment of 3s. 4d. to one of his associates named Ramston. A royal councillor, knight of the body, steward of the forest of Essex, and counted among the king’s confidants, Montgomery was in an advantageous position to secure a writ of supersedeas on behalf of the Celys to halt the progress of royal justice from proceeding any further against them. A subsequent letter from Cely on 28 November lamented that the favour ‘haue coste myche mony’ but accepted that the alternative would have been much worse if ‘ Sur Thomas Mongewmbre had not beyn howr good master hyt wholld a coste myche mor’.

The perception Montgomery enjoyed among his contemporaries that he was a suitable ‘good lord’ capable of exercising his will upon the course of royal justice was a testament to the strides he had made in his career under Yorkist rule. Prior to 1461, Montgomery faced obscure prospects as a younger son lacking a proper endowment to sustain himself. It was only after his staunch support for the Yorkist cause that his fortunes were rewritten. Montgomery’s rise to prominence amid the traumatic political change sparked by the Wars of the Roses was a trajectory repeated by many among the aristocracy.