Rake’s progress – An Irishman’s Diary on the life, loves and wagers of Thomas ‘Buck’ Whaley

'I was born with strong passions, a lively imaginative disposition and a spirit that could brook no restraint," begins Buck Whaley's Memoirs. This is what might fondly be called understatement. Because Thomas "Buck" Whaley led a life for which the word chequered scarcely does justice.

Born 250 years ago on December 15th, 1766, in Dublin, Whaley in adult life inherited a fortune, gambled heavily, lost his fortune, fought duels and generally led a debauched life.

After travelling the Continent, he found himself in Paris, where he conceived a plan (unsuccessful, as it happens) to rescue Louis XVI from the guillotine.

Thomas Buck Whaley also served as an MP in the Irish parliament.

In one respect, Buck Whaley was a fine role model for many politicians on the windy side of the law. He accepted substantial bribes from both factions in the Act of Union negotiations.

But it was a journey that Whaley undertook to Jerusalem for a wager that marked him out as a true adventurer.

Having dinner one evening with William FitzGerald, Duke of Leinster, the topic of Jerusalem came up. Even back then, this was a notoriously tetchy part of the world.

No matter, Buck bet that he could journey to the Holy Land and back within two years – a tall order in the 18th century. The wager was for £15,000, or well over a million euro in today’s money.

In October 1788 the Irishman embarked with a retinue of servants and a “large stock of Madeira wine”.

Whaley was destined to pass through some very dangerous places – not least the Ottoman Empire, which was then a centre of excellence for banditry and general skulduggery.

The Dublin man was perhaps fortunate in that a local ruler called Ahmed al-Jazzar “The Butcher” took a liking to him. Presumably that Madeira came in handy.

At any rate, he reached Jerusalem safely. Whaley later boasted of having “drunk his way around the Holy Places”, and for relaxation played handball against the Wailing Wall, surely a first for any Gaelic sportsman.

Whaley’s Jerusalem sojourn was verified by Franciscan nuns; Buck stayed at the Convent of Terra Sancta in the city, and a signed certificate from the superior corroborated his story.

It’s hard to know what his father Burn-Chapel Whaley would have made of this. As his name might suggest, Burn-Chapel was something of an anti-Catholic.

Buck Whaley arrived back in Dublin in the summer of 1789 to great acclaim, and collected his winnings.

Sadly, his life thereafter went into a downward spiral, including a spell in a debtors’ prison in London. Inevitably, he tried to escape but was unsuccessful.

On his eventual release, Whaley fled to the Isle of Man. Little is known of his time there but he evidently found sufficient funds to build a house.

Whether to win a bet, or on romantic whim, the Dublin man undertook to “live upon Irish ground without residing in Ireland”. Accordingly he had Irish soil shipped out to the Isle of Man to form the foundations of his house.

Less than four years later, in 1800, Whaley made a last fateful journey to England. En route to London he stopped off at the George Inn in Knutsford, where he died. He was only 34.

Contemporaneous newspapers ascribed his death to rheumatic fever. But unsurprisingly it wasn’t that straightforward. According to Sir Edward O’Sullivan, who published Whaley’s memoirs in 1906, “Tradition has preserved a more tragic account of his demise.”

It seems likely he was stabbed in a fit of jealousy by one of two sisters “to whom he was paying marked attentions at a time when each of them was in ignorance of his concealed attachment to the other”.

O’Sullivan adds that the lady who killed him “was said to have been won by Whaley from the Prince of Wales in a wager”.

Somehow, given what we know about the man, this has more of a ring of truth to it than “rheumatic fever”.

Thomas Buck Whaley was buried in Knutsford Churchyard.

But even his funeral was not without incident. O’Sullivan quotes a local historian: “A strange circumstance took place just before his funeral. The body had been placed in a leaden coffin . . . . the workmen had just made up the coffin, when Mr Robinson, an Irishman, who also was a dancing-master of that day, stepping upon the coffin, danced a hornpipe over the body.”

Somehow, it seemed a fitting tribute to this consummate adventurer and member of parliament. The jig was up, but his life might as well be celebrated by one.