The Gamble

By Thomas E. Ricks

After a bloody battle of Shiloh in 1862, with Union casualties scattered across the field and panic spread through out the union troops. Late that night, William Sherman found Grant smoking under a tree in the rain. Sherman muttered: “Well, Grant, we’ve had the devil’s own day, haven’t we?” Grant took a puff and replied without a pause: “Yep. We will get tomorrow, though.”

A similar mood hangs over Thomas Ricks’ The Gamble.

As America fumbles the Iraq war over many years from 2003-2006, a grim determination that the campaign may already be slipping away, sets in.

By 2006, the Iraq War had entered a phase where many American leaders struggled to publicly admit it was a disaster and bigger one in making. Sectarian killings were exploding. Baghdad neighborhoods were being carved apart through intimidation and ethnic cleansing. Al Qaeda in Iraq was growing stronger. American forces still dominated tactically. They could raid houses, seize roads, kill insurgents, and deploy overwhelming firepower almost at will and yet the larger trajectory of the war felt unmistakably heading towards an epic disaster.

Ricks describes a military that had become strangely detached from the society around it. American troops often operated from giant forward operating bases or from within the fortified cocoon of the Green Zone. They were launching missions into Iraqi neighborhoods and then withdrawing behind walls again. Officers began describing this bitterly as “commuting to war.” Soldiers would drive into dangerous neighborhoods during the day and then disappear at night, leaving civilians exposed to insurgents and militias the moment American patrols rolled away.

That phrase becomes one of the key psychological turning points in the book.

Because counterinsurgency wars are fundamentally about building trust, permanence, and daily security. Civilians do not risk cooperating with you if they believe you will vanish by sunset.

What makes this part of The Gamble so striking is that the intellectual push for the surge did not really come from the institutional Army itself. In many ways, Ricks portrays the American military establishment as deeply resistant to confronting what had gone wrong in Iraq.

The existing strategy had produced a bizarre situation: the most technologically sophisticated military in the world was failing at the oldest and most basic military task imaginable: providing everyday security to civilians.

What is remarkable in Ricks’ telling is how much of the intellectual energy behind changing strategy came from outside the active chain of command. Think tanks, retired generals, civilian academics, and policy intellectuals began filling a vacuum the military institution itself had failed to fill.

The American Enterprise Institute becomes an unexpectedly important player in the story. Ricks describes how AEI effectively became a kind of alternative war-planning hub at a moment when official strategy had stalled. Figures like Eliot Cohen helped frame the argument that the war could not be salvaged simply by killing more insurgents or handing off responsibility faster to Iraqi forces.

That mattered because much of the senior military leadership was still trying to reduce the American footprint in Iraq even as security collapsed.

General George Casey Jr., the top American commander in Iraq before Petraeus, becomes one of the central symbols of this tension in Ricks’ narrative. Casey believed that a visible American presence itself fueled the insurgency and that Iraqi forces needed to take the lead quickly. His approach emphasized transition and drawdown. But as sectarian violence exploded, critics increasingly argued that the strategy was creating a security vacuum faster than Iraqi institutions could fill it.

Retired General Jack Keane emerges almost like a backstage political operator, lobbying the White House and pushing for an overhaul of strategy and leadership. Ricks describes a strange period where retired officers, policy intellectuals, think-tank analysts, and dissenting insiders effectively began bypassing parts of the established military hierarchy because they believed the existing command structure had become incapable of correcting itself.

At the center of this transformation stood General David Petraeus. The book is part his biography.

Ricks portrays Petraeus as unusually adaptive. He is part scholar, part operator, part bureaucratic insurgent and an excellent athelete. Petraeus had already been involved in rewriting counterinsurgency doctrine and had helped bring historians, journalists, academics, and unconventional thinkers into military discussions. He understood that the war Iraq had become was not primarily a conventional battlefield problem anymore.

His right hand man, General Raymond Odierno also becomes one of the more interesting figures in the book. Earlier in the war, Odierno had developed a reputation for heavy-handed operations, but Ricks shows him adapting under the new strategy and becoming one of its key executors. One of the book’s recurring themes is that adaptability itself becomes a form of leadership. Some commanders remained trapped inside old assumptions. Others adjusted once reality made denial impossible.

Petraeus, AEI, Cohen and General Keane all advocate for a surge against strong political winds. And yet the surge does begin producing visible results.

American troops have been ordered to make camps outside the green zone and stop commuting to the war.

In parts of Baghdad again, markets reopened. Shopkeepers who had kept metal shutters down for months started selling vegetables and cigarettes again. Streets that had emptied by dusk saw children outside a little later into the evening. Some Sunni tribes, exhausted by the brutality of Al Qaeda in Iraq, turned against it and began cooperating with American forces. Small American outposts appeared inside neighborhoods instead of far away behind concrete barriers. Soldiers walked the same streets every day, learned names, drank tea with local leaders, and started looking less like raiders passing through and more like a permanent presence.

The killings dropped sharply in many areas during 2007 and 2008.

For a while, it felt as if Iraq had stepped back from the edge.

But underneath the quieter streets sat an uneasy question.

Had the country actually become more stable? Or had the violence simply been pressed downward temporarily?

The surge created breathing room. It bought time. It probably prevented Iraq from collapsing outright at that moment. The deeper fractures were still there. Sunni versus Shia distrust, militias embedded in politics, weak institutions, old fears waiting beneath the surface. American soldiers could reduce violence and create local trust block by block. What they could not do was guarantee what Iraq’s leaders would build once the immediate pressure eased.

That’s the lingering feeling at the end of the story.

Its simply whether the surge “worked,” but how close the United States came to strategic failure before enough people inside the system finally recognized they had to stop commuting to war and start living inside the reality they were trying to change.