Roberts’ name, which, to his surprise, transformed the atmosphere: ‘after that he had showed by whom he was sent thither, he was neither evil dealt with neither evil said to’. Neville grew thoughtful, acknowledging that he knew and respected Roberts. As Symson told his interrogators in the Tower, having been detailed to find information on Suffolk’s English supporters, he was aghast to find that they included Roberts, his own control.

Retracing his steps to Antwerp, he took a boat down the Scheldt estuary to the port of Arnemuiden, hitched a ride back to Erith on a barge loaded with salt fish, and returned to Cranbrook. But knowing what he now knew about Roberts, Symson was desperate to avoid him. Staying only one night with his wife, he went back up to Erith, winding up in the tavern where he was arrested. Rather than report to Roberts, he said, he had been going to take his information right to the top: to Sir Richard Guildford himself.6

There was much about Symson’s story that didn’t add up. Perhaps Sir George Neville had been playing a clever game: implying Roberts’ disloyalty, and sending the gullible Symson back to sow seeds of mutual suspicion and doubt among Henry’s intelligence network. But Symson’s abortive mission had proved him a useless spy, naming names at the drop of a hat – so bad, in fact, that it appeared less like a cock-up than a conspiracy. It looked for all the world as though Symson’s mission to make contact with Suffolk was undertaken for different reasons: that he, too, was part of the group of plotters intriguing on Suffolk’s behalf, and that, having been arrested, he was now looking for a plea-bargain by incriminating his superior, Roberts. And then there was the question of what on earth a casual labourer was doing working as a spy in the first place.

Whatever the case, for the royal officials in the Tower, and for Henry himself, trying to unpick the skein of tangled loyalties, the story took on wider implications for the kingdom’s security. Henry was well aware that, over the past years, Sir Richard Guildford had been losing his grip in Kent. If the likes of Symson and Roberts, Guildford men through and through, were – inadvertently or otherwise – sending out the message that all was not well with Guildford’s affinity, then Henry, too, had to think again. There was another big man in the region, one who had been flexing his muscles in a series of increasingly violent encounters with Guildford’s retainers. Not only was this man a Yorkist, he was Suffolk’s cousin.7

Throughout the troubled fifteenth century, violence in the volatile county of Kent had presaged wider conflict. In 1450, Jack Cade had marched on London at the head of five thousand Kentish insurgents in protest at Henry VI’s disastrous inability to rule – an uprising that had foreshadowed the country’s rapid descent into civil war. Kent’s strategic proximity to the Low Countries, Calais and London had made it a focus for repeated invasions, Yorkist and Lancastrian. Then came the Woodville-led uprisings against Richard III in 1483, in which the Guildfords and their man Walter Roberts had played a major role.8

After 1485, as Henry built up networks of royal influence in Kent, he turned to those who had already proved their loyalty during the turbulent years of exile and rebellion. At their apex was Sir Richard Guildford, with close links to Queen Elizabeth, to Sir Reynold Bray, to Lady Margaret Beaufort and to the king himself. But Guildford’s rise meant the eclipse of the region’s two most influential noblemen: John Broke, Lord Cobham and his brother-in-law George Neville, Lord Bergavenny. Both men, allies of Richard III, had been active in putting down the 1483 insurgency and, when Guildford and his fellow Woodville supporters fled into exile, had consolidated their power. But neither had been particularly happy with the rewards and opportunities offered them by Richard. They had stayed away from Bosworth, indifferent and aloof, and, with the opportunism of the age, seemed perfectly prepared to transfer their loyalties to the new regime.

To Henry, though, the very name of Neville spelled trouble. It was intimately associated with the house of York, whose matriarch, Cecily Neville, dowager duchess of York and mother to Edward IV and Richard III, remained a focus for insurgency: her household was closely linked to both the Warwick and Warbeck conspiracies until her death in 1495. Among those who had been involved with Warbeck and who subsequently fled with Suffolk was another Neville: Sir George, ‘the bastard’. Meanwhile, in 1492 the cool, calculating Lord Bergavenny died, and Henry had to deal with his young son and heir. Not only did the aggressive twenty-three-year-old come with all the wrong kind of dynastic and family baggage, but he was bound to be associated in Henry’s mind with Warbeck. For if Warbeck was really Richard duke of York, then the new Lord Bergavenny was his cousin.9

From the outset, Henry made it clear that he was watching the young noble. In 1492, as Bergavenny joined the king’s abortive invasion of France, Henry bound him over to guarantee his return – presumably to prevent him sloping off to join the brewing conspiracy. Warbeck’s attempted landing of 1495 didn’t help, either: in his search for local support, Bergavenny would probably have been one of the first names on his list. Bergavenny, though, appeared to keep his head down. He attended court ceremonies dutifully, and played a seemingly decisive role in the defeat of the Cornish insurgency at Blackheath in 1497 – fighting alongside his cousin, the earl of Suffolk.

As Henry’s uncovering of conspiracy in the mid-1490s made him fall back on servants of proven loyalty, Guildford’s position was reinforced, both in the royal household and in Kent, where his retainers manned the coastal defences and kept a sharp eye on disturbances and potential disloyalties in the region. The stream of royal favour flowed decisively in Guildford’s direction; he and his wife were popular at court, and his younger son became one of Prince Henry’s closest friends.

But Guildford had one fundamental flaw. He was a terrible businessman, utterly incapable of managing his own money – or for that matter, the royal household’s. When in 1494 Henry appointed Guildford as comptroller, the officer who vetted the household accounts, it seemed a barely conceivable promotion for somebody who had already been caught putting his hand in the royal coffers to service his own debts – though at that stage, in the middle of the Stanley conspiracy, Henry may have valued proven loyalty over financial probity. By the late 1490s Guildford’s investments in wardships and the land market had gone badly wrong. Defaulting on repayments for a string of ‘great charges’, he took out further loans. Despite the support of the king and of Guildford’s good friend Sir Reynold Bray, things got so bad that Henry was forced to appoint him a personal debt manager, the abbot of Battle. As Guildford’s fortunes declined, so did his ability to maintain his authority in Kent – and, by extension, the king’s influence too. It was no coincidence that, at the same time, Bergavenny’s influence started to spread.

Fuelled by an ingrained personal loathing for Guildford, the man whose regional dominance had eclipsed his own, Bergavenny started building up his power base, his men appearing more frequently in areas under Guildford’s control, handing out livery clothing, badges, colours and the promises that came with them: job opportunities, money, and the less tangible rewards that constituted a big man’s ‘good lordship’ – protection, influence, help with a lawsuit, or arranging a marriage.10 Trouble began to flare in towns and villages on the borders between Guildford and Bergavenny territory. Henry tried to keep a lid on the intensifying violence: between 1497 and 1503 he instigated over a dozen special commissions to provide rapid justice and attempt to snuff out the trouble at its source. But with Bergavenny poaching Guildford’s servants, the map of power in Kent was changing fast.

At Easter 1503, as Roberts and Symson had their first wary exchange, the confrontation between Bergavenny’s and Guildford’s retinues escalated dramatically. On Easter Monday, Sir Richard Guildford’s son George was presiding over the local court sessions at Aylesford, where he was steward, when a gang of Bergavenny’s men walked in, assaulted him, beat up his constable and bailiff, and made a bonfire of the court records. The following Monday, the same group went on the rampage, steaming through the local fair at Maidstone. In the inquests that followed, accusation and counter-accusation tumbled over each other: Bergavenny’s men said that Guildford had started it, deliberately provoking trouble by swaggering about in Aylesford – which was, after all, Bergavenny’s manor.11

As much as Suffolk’s conspiracy, it was this local turf war, with its packs of aggressive retainers, that was the context for the arrest of the drunken Symson in Erith that summer. The clash of allegiances, in fact, may have lain directly behind the encounter, for the landlord who plied Symson with beer before reporting him to the local authorities, Thomas Broke, was almost certainly one of Bergavenny’s men. Broke came from the village of Crayford, some two miles south and inland from Erith. Lying near Dartford on the main London to Canterbury road, it fell squarely within the territory of Lord Cobham, who was close to Bergavenny, his son-in-law, and was increasingly in his shadow. Thomas Broke was very probably a retainer of Cobham’s; he may also have been related to a ward of the same name that Bergavenny bought from Cobham a few years later. Financial motives were bound up in his informing, too: this was the chance to make some quick cash, spinning Symson’s drunken tall tale into a case of genuine sedition ‘for to have a bribe’.

Symson’s arrest, and his subsequent deposition against Roberts – a tale of doubtful loyalties, tangled affinities and local vendettas – drove home to Henry what he already knew.12 Guildford, the king’s man, was losing control in Kent – and consequently, so was the king. Bergavenny’s influence, on the other hand, was everywhere. Faced with a disastrous breakdown of authority in the region, a situation amplified by the

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