Buck Whaley lacking much in cash
And being used to cut a dash
He wagered full ten thousand pound
He’d visit soon the Holy Ground
— Verse from a Dublin ballad of the 1780s

Born in Dublin in 1766, Whaley’s father died in 1769, leaving an estate that included a town-house on St Stephen’s Green, land in Co Wicklow and £60,000. The estate generated an income of £7,000 per annum which became available to the young Whaley when he reached the age of eighteen.

At the age of sixteen, Whaley was sent to Europe on the Grand tour, accompanied by a tutor and with an allowance of £900, a sum that proved to be inadequate. He settled in Paris for some time, maintaining both a country residence and town house, but was forced to leave Paris when his cheque for the amount of £14,000, to settle gambling debts accrued in one night of gambling, was refused by his bankers, the La Touche bank.

Following his return to Dublin, Whaley, at the age of eighteen, was elected to the Irish House of Commons in 1785 representing the constituency of Newcastle, Co Dublin.

While dining with William FitzGerald, the Duke of Leinster at Leinster House, in response to a question regarding his future travel plans, Whaley flippantly mentioned Jerusalem. This reply led to wagers totalling £15,000 being offered that Whaley could not travel to Jerusalem and back within two years and provide proof of his success. The reasoning of those offering the bets was based on the belief that, as the region was part of the Ottoman Empire and had a reputation for widespread banditry, it would be too dangerous for travellers and it would be unlikely that Whaley could complete the journey.

Whaley embarked from Dublin on 8 October 1788, with a retinue of servants and a ‘large stock of Madeira wine’ to cheers from the large crowd assembled at the Dublin quays. Whaley and his companions made their way to Jerusalem, arriving on 28 January.

During his visit, he stayed at a Franciscan monastery, the Convent of Terra Sancta. It was a signed certificate from the superior of this institution, along with detailed observations of the buildings of Jerusalem, that would provide the proof needed to prove the success of his journey. Whaley later boasted of having ‘drunk his way around the Holy Places’, and for relaxation played handball against the Wailing Wall. They stayed for little over a month, before returning to Ireland overland.

Whaley arrived back in Dublin in the summer of 1789 to great celebrations and collected the winnings of the wager. The trip cost him a total of £8,000, leaving him a profit of £7,000.

Following his Jerusalem exploit, Whaley remained in Dublin for around two years and later spent time in London and travelling in Europe, including Paris during the Revolutionary period.

Due to mounting debts, he was forced to sell much of his estate in the early 1790s and these financial problems also led to his departure from Dublin. Whaley, accompanied by his companion, a Miss Courtney, and their children, left Dublin to take up residence in the Isle of Man, where he had a house built near Douglas. Nicknamed ‘Whaley’s Folly’, this house later became the Fort Anne hotel. The house became another part of another story, as it was reported that the house was built on soil imported from Ireland, so Whaley could win a bet that he could ‘live upon Irish ground without residing in Ireland’.

A recovery in the state of his finances enabled Whaley to be re-elected to the Irish House of Commons, this time representing the constituency of Enniscorthy from 1798 until his death in 1800.Whaley is said to have accepted bribes for his vote from both sides to support and later oppose the Act of Union.

Whaley wrote his memoirs in 1797, but these were suppressed by the executors of his estate and remained unpublished until 1906.