In the months to come, reliable intelligence proved to be a precious commodity, and spies seem to have infiltrated both camps. In late September 1191 Saladin narrowly averted a potentially disastrous leak when a group of eastern Christians travelling through the Judean hills were seized and searched. They were found to be carrying extremely sensitive documents–letters from the Ayyubid governor of Jerusalem to the sultan, detailing worrying shortages of grain, equipment and men within the Holy City–which they had intended to present to King Richard. Meanwhile, to furnish a regular supply of Frankish captives for interrogation, Saladin engaged 300 rather disreputable Bedouin thieves to carry out night-time prisoner snatches. For Latin and Muslim alike, however, knowledge of the enemy’s movements and intentions was always fallible. Saladin, for example, was apparently informed that Philip Augustus had died in October 1191. Perhaps more significantly, the Lionheart persistently overestimated Saladin’s military strength for much of the remainder of the crusade.

Throughout autumn and early winter 1191, Richard eagerly maintained a regular dialogue with al-Adil, and, to begin with at least, this contact seems to have been hidden from the Frankish armies. In part, the king must have been driven to negotiation by the rumour that Conrad of Montferrat had opened his own, independent, channel of diplomacy with Saladin. As always, the Lionheart’s willingness to discuss avenues to peace with the enemy did not indicate some pacifistic preference for the avoidance of conflict. Negotiation was a weapon of war: one that might beget a settlement when combined with a military offensive; one that would certainly bring vital intelligence; and, crucially in this phase of the crusade, one that offered an opportunity to sow dissension among the ranks of Islam.

Even before leaving Jaffa, Richard entered into an intensive period of communication with al-Adil between 18 and 23 October. Initially, the king set out to gauge the enemy’s attitude towards Jerusalem. He wanted to explore the possibility that Saladin might relinquish possession of a city that Richard bluntly stated ‘is the centre of our worship which we shall never renounce, even if there were only one of us left’. But al-Adil conveyed an unequivocal response from the sultan, emphasising Islam’s own reverence for the Holy City and urging the Lionheart ‘not to imagine that we shall give it up, for we are unable to breathe a word of that amongst the Muslims’.

Richard then made an audacious change of tack–one that surprised his adversaries at the time and still confounds modern historians to this day. The king had already made a point of cultivating an amicable relationship with al-Adil, apparently describing him as ‘my brother and my friend’ in conversation. He now took the far grander step of proposing an extraordinary marriage alliance between Latin Christendom and Islam, in which al-Adil would be wed to Richard’s own sister, Joanne. This union would form the basis of a peace agreement in which ‘the sultan should give to al-Adil all the coastal lands that he held and make him king of [Palestine]’, with Jerusalem to serve ‘as the seat of [the royal couple’s] realm’. This new polity would remain part of Saladin’s empire, but Christians would be given free access to the Holy City. Al-Adil and Joanne would command the region’s castles, while the Christian Military Orders would take control of its villages. The pact would be sealed by an exchange of prisoners and the return of the True Cross. With a flourish of seeming magnanimity, the Lionheart proclaimed that the acceptance of this deal would bring the crusade to an immediate end and prompt his return to the West.

Because this offer was not recorded in any surviving contemporary Christian source (being mentioned only in Arabic texts) it is difficult accurately to assess how such an apparently outrageous arrangement might have been greeted by Richard’s Frankish compatriots. The Lionheart seems to have kept the entire affair a closely guarded secret, even initially from his sister, but whether he took the whole idea seriously, or whether it was merely intended as a ruse, remains uncertain. What is clear is that al-Adil viewed it as a genuine proposal. In diplomatic terms, Richard’s proposition possessed a masterful subtlety. Alive to the potential tensions between Saladin and al-Adil–the latter’s position as trusted brother being balanced by the threat he posed to the sultan’s son and heir–the English king made an offer that al-Adil could not ignore, but one that could also make him appear to be harbouring personal ambitions. Acutely aware of this implication, al-Adil refused to convey the news of Richard’s scheme to Saladin in person, instead deputising Baha al-Din, instructing him to speak with strict caution.

Saladin actually agreed to the terms, although he may have believed that Richard would never go through with the plan and was merely trying to ‘mock and deceive him’. Certainly, within a few days the Lionheart sent news that his sister would be unable to marry a Muslim and now suggested that al-Adil should convert to Christianity, leaving ‘the door open for negotiations’.⁸⁵

A few weeks later, with the Third Crusade now grinding out its advance on Judea, Richard once again requested a parley. He and al-Adil met in an opulently appointed tent, pitched just beyond the Muslim front line at Ramla, on 8 November 1191. The atmosphere was almost convivial. The pair exchanged ‘foods, luxuries and presents’, tasting delicacies from their respective cultures; Richard asked to hear some Arabic music and a female musician was duly ushered in to entertain him with singing and the playing of a harp. Having talked through the day, ‘they parted’, in the words of one Muslim witness, ‘in amity and good spirits as firm friends’, even though the Lionheart’s repeated requests for a direct meeting with Saladin were declined.

Now, for the first time, the king’s negotiations with the enemy became public knowledge in the crusader camp, prompting considerable criticism. One Christian eyewitness noted that Richard and al-Adil ‘seemed to develop a sort of mutual friendship’, exchanging gifts including seven camels and an excellent tent. The general feeling among the Franks appears to have been that this diplomacy was ill advised. The Lionheart was said to have been fooled by the façade of generosity and goodwill into delaying the advance on Jerusalem–an error ‘for which he was much blamed and much criticised’–and outmanoeuvred by Saladin’s brother, who ‘trapped the overly credulous king with his shrewdness’. This notion of Richard as a befuddled pawn, manipulated by the devious political operator al-Adil, does not match up with the depiction of the Lionheart as a diplomat by Muslim sources. Indeed, the Mosuli chronicler Ibn al-Athir openly praised Richard, noting that ‘the king [met with al-Adil] as a skilful stratagem’.

In fact, the English king seems to have been a wily negotiator. A different man might have felt stymied by Saladin’s continued refusal of direct dialogue, but Richard sought to turn this factor to his advantage. On 9 November he sent the sultan an artful message, capitalising on the concessions made weeks earlier: ‘You have said that you granted these coastal lands to your brother. I want you to be an arbitrator between him and me and to divide these lands between [us].’ The Christians would need ‘some hold on Jerusalem’, but he wanted there to ‘be no blame on [al-Adil] from the Muslims and none on me from the Franks’. Richard’s rather devious underlying intention was to shift the whole basis of the negotiations, encouraging Saladin to think of himself as a magnanimous arbitrator and not an arch-opponent. At least some of the sultan’s advisers ‘were greatly impressed by this [approach]’.⁸⁶

In the field of diplomatic machination, however, Saladin was, at the very least, Richard’s equal. Throughout the autumn, the sultan had been in contact with Conrad of Montferrat, a fact he made no effort to hide from the Lionheart–indeed, Conrad’s envoy even occasionally ‘went riding with al-Adil, observing the Franks as the Muslims engaged them in battle’, a spectacle which, it was believed, prompted the English king to redouble his own efforts at negotiation. Looking to exploit the rift between Richard and the marquis, Saladin pushed for a ‘show of open hostility to the Franks from overseas’, promising that if Conrad attacked crusader-held Acre he would be rewarded with an independent principality including Beirut and Sidon. The sultan juggled the negotiations with Richard and Conrad with panache, even lodging their respective envoys in different parts of his camp on the same day, all the while aiming, in the words of one of his advisers, ‘to cause dissension amongst them’.