get others to join in a wager with him.35 In July 1787 he had told his mother that he intended to set off for Jerusalem that autumn, but she feared he was too weak following his illness and hoped he would postpone the trip until the following year.36 She had got her wish, but by 1788 the expedition was back on the agenda with a vengeance and betting began in earnest.
The precise terms of the wager are unclear, but it seems that the odds were placed at two to one against Whaley completing the trip, so that he stood to gain £2 for every pound he staked.37 Also, the expedition had to be completed within a certain time. Whaley himself put it at two years (W, 35) but other reports suggest a more limited timeframe: twelve months, fourteen months,38 or that ‘he should visit Jerusalem in the space of 12 months … there is no limitation as to the time of his return’.39 The patrons of Daly’s Club were the heaviest subscribers to the wager but many other members of the gentry and nobility also put their names down, among them the Earl of Grandison. Known for turning himself out in fine velvet embroidered with jewels, Grandison was said to be ‘very ingenious in the art of wasting the most possible money in the least possible time’.40 Under the terms of his bet with Whaley, made on 22 February 1788, he promised to pay him £455 ‘upon his return to Dublin from Jeruzalem’.41 This was just one of many individual wagers and when all were added up the amount Whaley stood to gain ran into five figures. He put the total at around £15,000, but other reports specify a larger sum: anything between £20,000 and £40,000.42 Whatever it was, it was a huge amount, at least €6 million in today’s money. But then gambling was one of the great obsessions of the eighteenth century. Wagers were laid on all sorts of sporting events, from prize-fighting to horseracing, but in theory one could bet on the outcome of almost anything. ‘There were bets on lives … on politics, on others’ bets, on every vagary of public and private life.’43 The famous dandy Richard ‘Beau’ Nash (1674–1761) had once ridden naked on a cow for a wager, and in 1785 Lord Derby undertook to pay Lord Cholmondeley 500 guineas ‘whenever his lordship fucks a woman in a balloon one thousand yards from earth’.44 Whaley himself claimed that he once jumped from the second-floor window of a Dover hotel ‘over the roof of the mailcoach that was then standing near the door. By laying mattresses in the street to break the fall, I performed the feat and had the honour of winning the wager.’45 (W, 326–7)
Eccentric as these bets were, gambling on something as dangerous and unpredictable as a journey to Jerusalem was all but unheard of. This was despite the fact that the Holy City, once thought to be the centre of the world, had exerted a powerful magnetism for centuries. Christian pilgrims had flocked there since the early Middle Ages, and the Crusaders had captured and held the city for nearly a hundred years. But by the early fourteenth century the Crusaders were a spent force and over the centuries that followed the flow of European pilgrims to the Holy Land slowed dramatically. By the eighteenth century few Europeans – and even fewer Irish46 – were travelling to Jerusalem. In the present age of online booking it is hard to conceive just how out of bounds most people regarded Jerusalem. One might almost as well have proposed a trip to the South Pole. To travel there for a wager was unthinkable, but as ever Whaley was galvanised by the thought of doing something that had not yet been accomplished. Indeed it was a seminal moment in his life: had it not been for the bet and the expedition that followed, it is unlikely he would be remembered today. But his track record of shambolic misadventure and profligacy did not inspire confidence, and the journey that lay ahead was so fraught with hazards that many reckoned his chances of winning the bet to be slim indeed. They ‘never imagined that a young man of his volatile disposition, would seriously engage in such a distant expedition’.47
Other than his volatility and unreliability, there were plenty of reasons for expecting Whaley to fail. The most efficient way to get to Jerusalem was to sail through the Straits of Gibraltar and down the Mediterranean, but a voyage would take several weeks and was likely to be hindered by unfavourable weather. Violent storms were frequent and could easily wreck a ship and drown its occupants, while adverse winds and dead calms could hold up the progress of a vessel for days on end. Apart from that there was the lurking possibility of attack by pirates or the naval fleets of hostile powers. Even if Whaley survived the perils of the sea, dry land presented hazards of its own. As well as visiting Jerusalem he planned to make overland detours to other places of note, in particular the city of Constantinople (Istanbul). But most land routes were ill-equipped to accommodate travellers. Unfavourable terrain, bad roads and bad weather were to be expected, along with accommodation that ranged from poor to abysmal to non-existent. Meanwhile there was an ever-present risk of attack by bandits or other hostile parties.
The political situation in the Near East was another cause for concern. The region Whaley planned to visit was part of the Ottoman Empire, the greatest power in the Muslim world and a place of ‘mystery, anxiety and fantasy’.48 Following its emergence in Turkey in the fourteenth century, the Empire had grown to become one of the largest and most formidable on earth, comprising Turkey, Greece, the Balkans, the Caucasus, Syria, Palestine and large parts of Arabia and northern Africa. The Ottoman sovereign, the Sultan (also known as the ‘Grand Seignior’ or ‘Grand Seigneur’), was based in Constantinople as was the central government, the Porte. In the late eighteenth century, just as European imperial ambitions were increasing, the Ottoman Empire was in decline. Riven by internal turmoil, the Porte was losing control of some of the outlying regions, where local governors had become almost like autonomous rulers.49 Simultaneously, ongoing wars with the great powers of Europe threatened to result in the loss of other territories. For years Russia and Austria had been aggressively pursuing plans to carve up the European part of the Ottoman Empire between them, and in 1787–8 their belligerence lured the Sultan into the latest of a series of costly wars. On the eve of Whaley’s departure news was filtering through of clashes between Ottoman and Austrian armies on the Danube. Meanwhile the Russians were besieging the Ottoman-controlled city of Ochakov near the Crimea, a protracted engagement in which the Turks would ultimately come off the worst. The land war between the Ottomans and the Austrians was unlikely to hinder Whaley, but he risked being caught up in the hostilities with the Russians if they spread further south. In previous conflicts, much of the fighting had taken place in the Aegean, for instance at Çeşme near Smyrna (now Izmir), where Russian ships had destroyed an Ottoman fleet in 1770.
Whaley would be sailing directly through these seas. Commenting on his planned route, one newspaper referred ominously to ‘the disturbance which affects the scenes thro’ which he is to pass’.50 Also, those in authority would have to be dealt with and perhaps placated. Worryingly, the road to Jerusalem led through the Ottoman province of Sidon, the domain of a ruthless governor known as al-Jazzar, ‘the Butcher’. In addition, the cultural differences between the West and the Ottoman world had to be taken into account. As a European Christian travelling in lands that were predominantly Muslim, Whaley would inevitably attract curiosity, if not hostility. If he could find ways to blend in with the locals, or at least make himself less conspicuous, so much the better. Whaley did take the time to apprise himself of many of these realities by reading the accounts of Europeans who had recently travelled in the Ottoman lands, among them Francois Baron de Tott’s Memoirs … Containing the State of the Turkish Empire and the Crimea (1785) and Constantin de Volney’s Travels Through Syria and Egypt in the Years 1783, 1784, and 1785, an edition of which was published in Dublin in 1788. Volney’s work was full of useful information on the places, people and dignitaries Whaley expected to encounter.51
Yet there was one final, unpredictable force that threatened the success of his expedition: an epidemic disease whose very name inspired terror. The plague had killed millions in Europe before being all but eliminated there through improved sanitation, healthcare and the use of quarantines. But it remained rampant in the Near East and visited Constantinople almost every year. A particularly virulent outbreak in 1778 may have wiped out a third of the city’s population.52 These facts were not unknown to Whaley and while the other dangers of the journey and the ongoing wars and disturbances did not concern him much as he prepared to embark, he was terrified of falling victim to the plague.
By the summer of 1788 almost everything was ready for Whaley to begin his great undertaking, but shortly before his date of embarkation he stumbled once more on his Achilles heel. Early
