A few months after retiring as President Reagan's national security adviser, Robert McFarlane secretly flew to the last place anyone would have expected to see a senior American official in 1986 - Tehran. As part of the clandestine, illegal Iran-contra deal, McFarlane brought with him a shipment of weapons parts. In return, he hoped, the Iranians would use their influence to release the American hostages held in Lebanon. Unfortunately, the mission did not quite go as planned. When McFarlane's unmarked aircraft touched down, no senior Iranian officials were there to meet him. Picking through his luggage, security guards came across the gift he had brought to show his goodwill - a chocolate cake from a Tel Aviv bakery. But as it was Ramadan and the guards were fasting, it could hardly have been a less appropriate present.

Somehow, McFarlane's chocolate cake - rich, gooey and well intentioned, but misguided and mildly offensive - seems an apt symbol for the sorry saga of American intervention in the Middle East. His mission, needless to say, ended in disaster. The deal did nothing to hasten the return of the hostages; instead, its exposure crippled the Reagan administration, and McFarlane tried to kill himself a year later. Like so many American policymakers in the past half-century, he left office battered and bewildered by the politics of the Middle East.

Rich in irony and incident, Patrick Tyler's history of the White House and the Middle East would make instructive reading for the latest occupant of the Oval Office. Tyler is no radical: the United States, he writes, is still “the indispensable power in the Middle East”; but its mistakes “have cost countless thousands of lives” and “sundered landscapes once vibrant with diverse cultures”. His brisk, engaging book is a plea for “tolerance and accommodation” in American foreign policy. But if the past 50 years are any guide, it is likely to fall on deaf ears.

In essence, A World of Trouble consists of eight presidential portraits, showing how Eisenhower, Johnson, Nixon, Carter, Reagan, Bush, Clinton and Bush grappled with the dilemmas of power, oil and strategy from Suez to Iraq. If Tyler has a hero, it is his first subject, Eisenhower, the avuncular general-turned-golfer whose bumbling manner hid a shrewd political instinct. Unlike the McFarlanes of the past 50 years (of whom there were many), Eisenhower approached the Middle East with few ideals but a keen sense of political possibility, born of his experience in Europe during the second world war. Unlike his successors, he recognised the limits of American power and the perils of intervention in distant lands. When Britain and France invaded Egypt in 1956, for example, Eisenhower's opposition was crucial in ending the operation; Suez was his “finest hour”, Tyler writes. But even Eisenhower had his faults: by subordinating Middle Eastern politics to “the fight against international communism”, he “failed woeful-ly to address the deep-seated grievances of the region”.

An obvious objection to Tyler's argument here - and indeed to the premise of his book - is that nobody elected Eisenhower to address the grievances of the Middle East. Indeed, one might argue that a principal failing of American policy has been that successive presidents, obsessed with the region's strategic location and oil reserves, and heavily influenced by their friendship with Israel, have thought it their business to meddle in the affairs of a very distant and different part of the world.

Many of the disasters that Tyler chronicles are well known: the 1979 hostage crisis in Iran, for example, or GeorgeWBush in Iraq. But even supposedly effective presidents had their horror stories. Ronald Reagan, for example, made one of the most dreadful mistakes in American history by sending the marines as peacekeepers to Beirut in 1982. There, a year later, 241 servicemen were killed by a gigantic truck bomb, the marines' biggest loss in a single day since Iwo Jima, and a humiliating tragedy that Reagan's admirers often choose to forget.

The most obvious thread connecting all these blunders is the controversial relationship between Washington and Tel Aviv. Tyler does not go quite as far as John Mearsheimer and Stephen Walt, for whom the Israel lobby lies at the heart of American foreign policy; but he is nevertheless a keen critic of the special relationship between the United States and Israel. Indeed, what is perhaps most striking is the constant American appeasement in the face of Israeli aggression. “Don't lie to me! I'm sitting here watching it on CNN!” Reagan yelled down the telephone to Menachem Begin in 1982, after the Israeli leader had reneged on a promise not to bombard Beirut. But in typical fashion, Reagan did nothing about it - a pattern that has been repeated, by and large, ever since.

While Tyler's book jumps rather abruptly from episode to episode, and breaks little new ground in terms of analysis, it nevertheless makes a lucid and even-handed introduction to a deeply contentious subject. Reading it during the Israeli invasion of Gaza, it was hard not to be struck by the parallels between past and present, and not to be depressed by the miserable prospects for change. Whether President Obama will do better than his predecessors remains anyone's guess, but since he seems to share their sense of America's mission to the world, it is difficult to be optimistic.

A World of Trouble by Patrick Tyler
Portobello £25 pp640

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