Steven Simon’s Grand Delusion offers a sweeping, insider’s account of American policy in the Middle East from the Iranian Revolution in 1979 through 2023. It is a long book and covers more than forty years of good and bad decisions and unintended consequences. I found it far more ambitious than the typical foreign-policy postmortem.
For the longest time, I believed the United States was in the Middle East for one reason only: Oil. End of story. That explanation sounds clean and satisfying. It gives you a villain, a motive and a sense of closure. But Grand Delusion shatters that myth.
The U.S. did not walk into the Middle East with a master plan. It moved in with a purpose, stayed on and kept making decisions that made sense in the moment but felt ill-advised over time. Across forty years, Simon reveals a rhythmic pattern of error: a superpower convinced it was solving problems, when every move only multiplied the chaos.
Steven Simon is not some salty outsider throwing stones from the sidelines. He worked inside the system – serving under Ronald Reagan, then later working on Obama’s National Security Council. He had a ringside seat to every lever moving and every half-baked policy getting pushed through. This book is what that ringside view looks like once the dust settles.
What the book is really asking
How does the most powerful country in the world keep getting the same region wrong? This question serves as both the book’s underlying theme and the tantalizing mystery for anyone who has tracked decades of American involvement in the Middle East. Rather than providing a single smoking gun or blaming it all on one specific blunder, Simon avoids oversimplification in favor of a more nuanced analysis.
What emerges is a recurring pattern. A series of Middle Eastern policy blunders that spans every successive administration. Each administration arrives convinced it understands the problem and then, builds a policy around that delusion and ultimately, leaves the region in a more messed up state than before.
At one point, Simon notes that an entire administration shaped its actions around a threat that did not exist. The line is written about George W. Bush, but it serves as a broader indictment of the US approach – a morbid tendency to chase shadows while ignoring the shifting realities of the region.
Reagan: When Things Started Slipping
Simon begins with Jimmy Carter (1977-1981), who, contrary to popular belief, did not start off disastrously. His vision of Iran and Saudi Arabia as twin pillars was sound on paper. But the unexpected collapse of the Iranian monarchy and the onslaught of the Islamic Revolution derailed his plans.
The ensuing hostage crisis left the US humiliated on the global stage. Carter, Simon suggests, was unlucky. Then, came Ronald Reagan (1981-1989).
With Reagan, something fundamental shifted. Under his watch, the Middle East became a theater for American power projection. From Lebanon to Libya, from covert deals with Iran to the Iran-Contra scandal, American policy became a maze of contradictions. Iran-Contra affair, in particular, revealed a striking disconnect between Washington’s public rhetoric and its private dealings.
This was no astute statecraft, as Simon implies. It was a desperate attempt to patch holes in a sinking ship using whatever materials were at hand.
George H.W. Bush: Fighting the Wrong War
When George H. W. Bush (1989-1993) took office, the Soviet Union was in its death throes. Yet America’s geopolitical experts were still glued to the same dusty Cold War playbook. That intellectual lag led to one of the most consequential conflicts of the late 20th century.
By the time the tanks rolled into Kuwait in August 1990, the US was essentially using a map of a world that that had ceased to exist. It was a classic case of a superpower being “too big to adapt,” proving that sometimes the most dangerous thing in foreign policy is not a new threat, but an old one that refuses to die in the minds of policymakers.
The deeper failure came after the battlefield triumph. Iraqi army was routed in 100 hours yet the U.S.-led coalition stopped short of removing Saddam Hussein. His regime’s survival allowed him to crush internal uprisings and starve his population. As a result, the “Saddam Problem” dominated U.S. foreign policy for the next 12 years. Here Simon identifies a pattern that recurs throughout the book: Decisive victories… followed by unfinished business.
In my view, this was the moment America fell in love with the idea of “Clean War”. By halting operations halfway to avoid a quagmire, America inadvertently created the conditions for a far bloodier and more protracted one a decade later. Iran Conflict of 2026 is moving along the same lines, if you are paying attention.
Clinton: When Doctrine Becomes a Trap
If Reagan represented contradiction and Bush Sr. strategic inertia, Bill Clinton (1993-2001) brought the creaky doctrine of “dual containment” to the party. His administration treated both Iran and Iraq as equally hostile threats.
On a whiteboard in Washington, Dual Containment appeared mathematically sound. But in practicality, it shackled the U.S. to the region with no exit strategy. Simon writes:
“In the end, dual containment led to America’s containment by Iran and Iraq. It forced the U.S. to maintain a large military infrastructure in the Persian Gulf, embrace sanctions policies that strained relations with NATO allies and Arab states.”
The human cost of Clinton’s doctrine was immense, as sanctions targeted the many to punish the few across both Iran and Iraq. And, the real tragedy of his era was the aborted Conoco deal with Iran. A potential opening for diplomacy, shut down under political pressure.
And yet, Simon highlights that Clinton’s tenure was not without hope. He regards the Oslo Accords as the high-water mark of Clinton’s diplomatic efforts. For a brief window, peace between Israel and Palestine seemed plausible. And, then came the assassination of the Israeli PM Yitzhak Rabin, fueled by the right-wing hatred within Israel. With his death, whatever real chance existed for peace was snuffed out with him.
George W. Bush: War is easy. What comes after is not
The chapter on George W. Bush (2001-2009) is where Simon’s book hardens into something colder and more damning. From lamenting missed opportunities, Simon shifts gears to analyzing a manufactured catastrophe. He dissects an era where American policy wasn’t just misguided, but untethered from reality.
The Iraq War was sold on the back of phantom intelligence and non-existent weapons of mass destruction. Yet as Simon makes clear, the invasion itself was not the deepest failure. It was the absence of any coherent plan for the day after. By dismantling Iraq’s institutions and administration apparatus, the U.S. unleashed a wave of chaos that consumed the country.
The U.S. army was saddled with the task of stabilizing what had increasingly begun to resemble a failed state. But you cannot “stabilize” a country where your presence is the very thing fueling the insurgency. As Simon argues, Washington had sent a sledgehammer to perform a scalpel’s work: asking a conventional army to shoulder the delicate, political task of nation-building.
Reading this chapter, I felt like Simon is warning us that the most dangerous weapon in any administration isn’t a missile, it’s a conviction that can’t be corrected by the truth.
Obama: Restraint, With Consequences
Barack Obama (2009-2017) enters Simon’s narrative as something of an anomaly. Compared to Bush and Clinton, he was a reluctant strategist. He wanted the U.S. to pivot away from the hyper-interventionism of his predecessor.
Simon credits Obama as the first president to openly recognize the limits of American power in the Middle East. He understood that the Middle East was a trap to be avoided, not a prize to be won. In this context, the Iran Nuclear Deal (JCPOA) of 2015 was a diplomatic masterstroke – it marked a negotiated pause after decades of hostility.
That said, this restraint was its own double-edged sword. In Syria, for example, America’s decision to avoid direct intervention and choosing to arm the rebel groups produced a classic half-measure. Determined to avoid another Iraq-style quagmire, Obama helped create the worst of both worlds: a fragmented battlefield on which groups like ISIS could flourish.
Restraint by itself, Simon soberly concludes, does not guarantee stability.
Trump: Disruption Without Direction
Simon’s critique of Trump (2017-2021) is perhaps the most damning because it suggests that for four years, the most powerful country in the world stopped trying to lead and started trying to disrupt, leaving a fractured region for others to manage.
By torching the JCPOA without any viable alternative, Trump ripped out the last rusty guardrails and pushed the entire Middle East straight off the cliff. To his credit, Trump did achieve notable success with the Abraham Accords, normalizing relations between Israel and several Arab states.
While the Accords built a defensive wall, the killing of Soleimani kicked the hornets’ nest. It signaled to Tehran that the U.S. was done playing the containment game and had upgraded to a policy of targeted decapitation.
In Simon’s assessment, this was the phase where the seeds of the 2026 Iran Conflict were sown. The central lesson is stark: when you destroy a diplomatic framework and replace it with nothing but threats, you aren’t avoiding war, you are making it inevitable.
Biden: The Weight of Inheritance
Joe Biden (2021-2025) arrives at the end of the book, but not at the end of the story. He inherited a region shaped by four decades of accumulated decisions: a JCPOA lying in ashes and a hardened Israel-Palestine divide. And, an Iran that had little reason to trust negotiations. (As I write this in the first week of May 2026, that last point remains intact.)
Simon suggests that America’s future lies elsewhere. In the Pacific, in Europe and in its own hemisphere. But if recent events have shown anything, it is this: The Middle East does not let go easily.
It Was Never About Oil
If there is one overarching lesson in the book, it’s this: it was never about oil. Simon doesn’t say oil was irrelevant, but he argues it was never the central engine driving America’s massive military and diplomatic commitment.
Instead the real drivers were: a) Strategic positioning against the Soviet Union during the Cold War b) The security of Israel and c) The stability of Saudi Arabia.
And yet, even with these objectives, the outcomes were mixed at best – often disappointing and at times, self-defeating.
Why This Book Stays With You
What makes Simon’s writing so compelling is that he never sounds like a man trying to win an argument. Instead, he sits you down at the table where the decisions were actually made. You see the quiet trade-offs, the half-measures, the unintended ripples spreading across years and borders.
There are no sweeping condemnations, no theatrical outrage. What Simon offers is something rarer: a calm accumulation of choices and their often painful consequences.
That quiet discipline is what makes Grand Delusion an unputdownable read. Simon doesn’t tell you what to conclude. He shows you how things unfolded and then leaves you alone with the weight of it.
Final Take
We started this review by noting Simon’s identification of a recurring “pattern of errors.” By 2026, that pattern has become a circle. Simon’s hope for a “Pacific future” is currently being held hostage by a Middle Eastern past that refuses to stay buried.
As we sit here in May 2026, watching the U.S.-Israel-Iran Conflict stuck in a quagmire, Grand Delusion reads less like history and more like a live script. The grand delusion, Simon suggests, is thinking we can just swap the leaders while the same old disastrous story keeps repeating.
If you follow geopolitics, if you care about American power and its limits, if you want to understand how we got here without the usual noise and slogans – read Grand Delusion. It is the real thing.
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