Reimagining what “might have been” is something we all do with the past, with capital H history and the events of our own lives. In his book, Bob Thompson undertakes what he describes as a “ridiculously ambitious, one-person staff ride of the Revolutionary War.” (A “Staff Ride” is an educational tour for military officers, to learn from battles of the past). His goal is to consider the possible alternative outcomes for the battles of the American war of independence. He argues, “We don’t know this story as well as we should—or how easily the ending could have changed.”

Thompson is keen to take the reader along with him—assuming that we have about the same level of knowledge—and his enthusiasm shows through, in passages like this:

We don’t know nearly enough about the months-long catastrophe that was George Washington’s attempt to defend New York City in 1776. Fought on what would become some of America’s most expensive real estate—Brooklyn Heights! Midtown! The Upper West Side!—the New York campaign added up to a series of humiliating defeats or miraculous escapes, depending on who’s telling the tale. On the night of August 29, to take just one example, Washington and his badly beaten army were ferried across the East River from Brooklyn to Manhattan by a bunch of sailors and fishermen from Massachusetts.

But his bigger questions are what if it had gone differently for Washington, through which Thompson explores how lucky the American side had to be to come out the victors on many occasions. He points out:

We almost never think about what would have happened if neither the rebels nor the British had won the war. … But by 1781, a more likely scenario—fueled in part by French reluctance to throw more scarce resources at a cause that might be lost—was peace negotiations in which the European powers would hold all the cards, and which would, at best, preserve much of the territorial status quo.

Exhausting stalemates ending in truce were par for the course with many European land wars, so it would hardly have been unprecedented.

He attributes to personality clashes battlefield decisions that had huge ramifications. Bunker Hill “turned into a war-altering disaster for the British” because they “didn’t listen to Henry Clinton.” Clinton urged an early morning attack, but his colleagues rejected this suggestion because Clinton was “socially awkward” and they didn’t like him. Various degrees of pettiness among the officer class seem to affect both sides, in Thompson’s accounts. 

Thompson notes the way our understanding of the war has been shaped by cultural emphasis, which changes over time: “Until 1861, Revere was a regional hero, not a national one. But when one of the most popular poets in American history took an interest in him, he went permanently viral.” Which other revolutionary war figures would have higher billing if they’d struck the right note with tastemakers generations later? Indeed in more recent times, the popularity of Lin Manuel Miranda’s musical “Hamilton” has been credited with keeping the title character on the $10 bill.

Thompson’s comment about Revere’s “virality” matches his chatty tone throughout, as he attempts to see the battles on the modern landscape:

Militiamen took aim from behind the used Impalas at Mirak Chevrolet; flankers charged through the aisles at Stop & Shop, then looted Mystic Wine next door; noncombatants sought shelter behind the counter at Retro Burger & Ice Cream.

He compares the pace of marching soldiers with slow traffic on the Massachusetts Turnpike, trying to peel back the layers of the visible world to see the ghosts of the battles. Like reenactors, pulling on itchy wool jackets and squinting hard enough to feel they are in a real conflict.

While this is engaging, I wish I’d liked this book more. Thompson follows the tracks of old maps, searches for overgrown historical markers, and on the way through encounters tour guides, scholars, and amateur enthusiasts with their views of the various battles involved. He visits battlefields, retraces Benedict Arnold’s escape, analyzes Cornwallis’ tactical decisions, and recounts the role of various other players in their battle choices. He continues his search for “Unknown Dudes Who Accidentally Saved the Revolution.” Unfortunately, too much of it has the vibe of your friend from work telling you about his vacation in real-time, and the attempts to reimagine 1700s conversations in modern slang fall awkwardly. (Low blow, dad, says John Laurens.)

And while he’s focused entirely on the military conflict, there’s less attention paid to the greater geopolitical what-ifs. Not just what if this particular general hadn’t died, been called away, or made a particular decision on that day? But what if the crown had behaved differently towards the colonists? What if the British Caribbean colonies had thrown in their lot with the rebels? And what if the French king had realized what he was unleashing: that supporting a campaign for liberty on the other side of the Atlantic might presage the end of royalty in France? (It’s all very well to stick it to the British via their troublesome subjects; it stops being funny when it’s your own subjects storming the Bastille.)

Which launches other questions historians could ask. Should we look at Lexington and Concord not as America’s but as Britain’s revolution? Did the British, early adopters ever, actually sweep in the age of revolutions that carried across Europe? But having beaten others to the jump, this early rebellion actually served to inoculate the mainland of Britain from the further turmoil that swept away borders and rulers in the next half-century.

Scholars often fall into the inclination of wanting their pet event to be the turning point, the lynchpin, the event without which our world would be different. I tend to doubt there are such events or such people. Rather, events and individuals have the meaning we give them: if a particular battle had never happened at all, the test of arms would simply have come on another field. Thompson suggests, “What-if questions are as unanswerable as they are irresistible. Yet it’s essential to keep asking them, because one of our basic impulses when we think about the past, is to assume that things happened because they had to happen.” Yet this creates a loop, like the paradox of time travel. There is no answer, because the world doesn’t work that way.

Thompson tries to be even-handed about most of the actors. But the nitty gritty of who-said-what-to-whom leaves further gaps that 250 years can’t fill. We get some jostling for rank by ambitious officers and some tactical misjudgments by leadership, but not the biggest doubts playing out in the minds of those wavering about the wisdom of war at all. His own what-if frame is too narrow. Never asked is, What if there never was a revolution?