Tony Blair stepping down as a Middle East peace envoy after eight years was greeted almost everywhere with a mixture of harsh criticism, derision and relief. He had reportedly long been allocating three days a month to the job and devoting the rest of his time to his business interests.

Blair is a member of a strange but exclusive club consisting of British and American political leaders whose careers have been blighted or terminated over the past century by calamitous involvement in the Middle East. On the British side members include Winston Churchill, David Lloyd George and Anthony Eden, and among the Americans are Jimmy Carter, Ronald Reagan and George W Bush.

Do the different crises in the Middle East with which these six men failed to cope successfully have anything in common? Were similar mistakes made, and why has the region become such a graveyard for political reputations?

Blair’s departure coincided almost to the day with the centenary of the moment on 18 March 1915 when an Anglo-French fleet entered the Dardanelles with the purpose of fighting its way through to Istanbul. As First Lord of the Admiralty, Churchill was a prime advocate of the plan which failed disastrously when Turkish mines and guns sank three battleships and seriously damaged three others. Shortly afterwards he supported the landing of ground troops on the Gallipoli peninsula on 25 April, which ended in total defeat eight months later, after a quarter of a million British and French troops had been killed or wounded, along with a similar number of Turkish soldiers.

A British tank in a destroyed Egyptian street during the 1956 Suez crisis (Getty)

The British attacked the rugged and highly defensible Turkish positions at Gallipoli primarily because a series of Turkish defeats in the first months of the First World War led Churchill and Lord Kitchener, Secretary of State for War, to underestimate their powers of resistance. Reading about this in Eugene Rogan’s highly informed and intelligent book, The Fall of the Ottomans: The Great War in the Middle East 1914-20, I was struck by the parallels between what happened then and the US and British invasion of Iraq in 2003. In both cases there was the same over-confident underestimation of the opposition, and wilful ignorance of the dangerous physical terrain at Gallipoli and the equally lethal political landscape of Iraq. In the wake of this failure Churchill was demoted, and his reputation never quite recovered until he became Prime Minister in 1940.

Seven years after Gallipoli, in 1922, Lloyd George lost his job as prime minister when he almost went to war with Turkey after backing the failed Greek invasion of the Turkish mainland. I have always thought that Blair resembled Lloyd George more than any other British prime minister in his ambition, self-belief and ability to manipulate others. Both men imagined with good reason that they could successfully manoeuvre their way towards ingenious solutions for intractable problems. They had their greatest triumphs in Ireland: Lloyd George negotiating an end to the Irish War of Independence in 1921 and Blair bringing peace to Northern Ireland with the Good Friday Agreement in 1998.

Tony Blair: A career of controversies Show all 11 1 /11 Tony Blair: A career of controversies Tony Blair: A career of controversies The Tony Blair 'selfie'.. A journalist takes a picture of Kennard Phillips 'Photo Op', depicting Prime Minister Tony Blair taking a 'selfie' in front of an explosion in Iraq, during a press viewing of the exhibition Catalyst: Contemporary Art and War Tony Blair: A career of controversies Protesters pictured outside the QEII Conference centre in London in 2011 as former British PM Tony Blair give his evidence in the Chilcot Iraq Inquiry Tony Blair: A career of controversies David Lawley-Wakelin, who disrupted Tony Blair’s testimony at the Leveson Inquiry by bursting into the court Tony Blair: A career of controversies Blair giving evidence Tony Blair: A career of controversies Tony Blair visiting troops in Iraq in 2007 Tony Blair: A career of controversies Blair meeting with troops in Basra, Iraq in 2003 Tony Blair: A career of controversies Britain's Prime Minister Tony Blair speaks to British soldiers at Divisional Headquaters in Basra, May 2007 Tony Blair: A career of controversies British Prime Minister Tony Blair eats dinner with British troops in Basra, Iraq, 21 December, 2004 Tony Blair: A career of controversies Syrian president Bashar El Assad during his official visit to the United Kingdom in 2002. Mr Blair tried to engage Mr Garcia in a conversation about Syria. The former Prime Minister made clear he was very much in favour of military intervention last summer. Tony Blair: A career of controversies Syrian president Bashar El Assad and wife Asma during their official visit to the United Kingdom in 2002. Mr Blair tried to engage Mr Garcia in a conversation about Syria Tony Blair: A career of controversies Former Prime Minister Tony Blair's signature adorns a program he signed for an Iraq veteran during a reception at the Guildhall in London following the service of commemoration at St Paul's Cathedral honouring UK military and civilian personnel who served in Iraq

Crucial to their success was that they both knew a great deal about Ireland. Lloyd George because Ireland had been at the centre of successive British political crises for half a century. Blair because he is half-Irish, his mother Hazel coming from a family of Protestant farmers in Donegal. Blair’s autobiography, a fascinating and funny book, has a telling story about his grandmother and her undiluted Protestant bigotry. Blair went to see her when she was so far gone with Alzheimer’s that she scarcely recognised him. Blair writes: “As I patted her hand, she suddenly grabbed mine, opened her eyes wide and said: ‘Whatever else you do, son, never marry a Catholic.’ Everything else had disappeared from her mind, but left at the bottom was the residue of sectarian aversion.”

Despite taking Britain into the Iraq war of 2003 and living in the Middle East for long periods since he was prime minister, Blair has never shown anything like the same sensitivity to the politics of the region as he once had in Ireland.

Giving evidence to the Chilcot inquiry in 2010, Blair gave the impression of never taking on board the sectarianism and corruption of the government in Baghdad – that he had helped place in power. The rise of Islamic State to rule a third of Iraq must have come as a complete surprise, going by his up-beat view of Iraq at that time. It would be intriguing to know what advice Blair gives his wealthy clients in the Gulf and central Asia about future developments in Iraq, Syria and Libya.

Is anything to be learned from the Suez crisis of 1956 which ended the career of Anthony Eden and proved that Britain could not act in the Middle East contrary to American wishes? The demonisation of President Nasser as Hitler reborn was very similar to the demonisation of Saddam Hussein (though he was much more of a demon than Nasser ever was). In both cases self-deluding propaganda held that a single ruler of immeasurable evil was responsible for the troubles of Egypt and Iraq. I remember a neurosurgeon in a hospital in Baghdad saying to me just after the fall of the city in 2003 that “the Americans should remember that even Saddam found it difficult to rule Iraqis”.

After the Suez crisis, the United States became the leading Western power in the Middle East and its presidents became more likely than British prime ministers to end up on the political casualty list. Jimmy Carter had bad luck with the outbreak of the Iranian revolution, the fall of the Shah and the seizure of hostages at the US Embassy in Tehran. There was not a lot he could do about it. Ronald Reagan was permanently damaged by Iran-Contra, the bizarre attempt to persuade the Iranians to free US hostages taken in Beirut in return for arms and use the money from the arms sales to illegally fund the Nicaraguan Contra rebels. It should always have been obvious that the damage from this weird plot going wrong far outweighed any possible benefits. It is also probably a mistake to try to outdo the Iranians when it comes to deviousness.