The Strategists: Churchill, Stalin, Roosevelt, Mussolini, and Hitler 

– How War Made Them and How They Made War

By Phillips Payson O’Brien

Dutton 2024

Phillips Payson O’Brien, Professor of Strategic Studies at the University of St. Andrews at Fife and the author of 2019’s memorably interesting The Second Most Powerful Man in the World, opens his new book, The Strategists (append an endless subtitle), by making a distinction that will be familiar to his students but perhaps not to his general readers: the difference between strategy, the kinds of operational plans many generals and admirals could formulate, and grand strategy, which only their bosses could impose. Grand strategy, O’Brien writes, has two distinguishing characteristics: it’s implemented by people whose authority cannot be countermanded by a higher individual authority (dictators, naturally, but also canny elected officials), and it involves “actions above the conduct of operations on the battlefield.” 

O’Brien’s central characters, German dictator Adolf Hitler, Italian dictator Benito Mussolini, Russian dictator Josef Stalin, British Prime Minister Winston Churchill, and US President Franklin Roosevelt, “the Five” as he dubs them, all engaged in grand strategy, and in the author’s fleet, page-turning running profiles of each, the endemic weaknesses of grand strategies are revealed even more clearly than their strengths. It requires an almost eerie combination of ruthlessness and egotism to rise to the levels of power the Five achieved, and that combination is never conducive to the supple adaptability that good strategizing requires. Although even here, there are differences: O’Brien points out, for instance, that although Stalin was as savage a figure as his erstwhile partner Hitler, he was better at changing his plans in the face of new information. 

The book charts the interests and mental habits of these five men, and it makes for easy, unchallenging reading throughout. O’Brien’s offhand descriptions are uniformly fascinating, as when he’s discussing Churchill’s return to the Admiralty and the new tone he infused: “As opposed to the subdued and schoolmasterly [Neville] Chamberlain, he spoke about British defiance in bright colours, with the added authority of his past experiences of war.”

And since three out of his five were dictators, O’Brien is able to concentrate a good deal on the ways dictators use and abuse grand strategy; he makes the obvious contemporary connection to Vladimir Putin’s invasion of Ukraine and references “Hitler’s fascination with the largest, heaviest firepower,” which “reveals something common in dictators: a stress on strength, without a corresponding ability to understand rational trade-offs.”

O’Brien characterizes Hitler as the most delusional of the Five but Mussolini as the most pathetic, which renders all the more interesting the fact that Mussolini is the book’s most interesting, even moving character. He usually seems to lack the inhuman pathology of Hitler and Stalin, but he’s usually often careful to avoid displaying the feral opportunism of Churchill and Roosevelt. And as the book’s action increases, he’s regularly worried that his own abilities at grand strategy are being eclipsed by the other members of the Five:

When Hitler conquered Poland without Italy … Mussolini started to fear that he was missing out not as a peacemaker (which was never really his forte) but as a conqueror (not his greatest skill either, it must be said). Moreover, the dictator who had cultivated such a hyper masculine image worried that he had humiliated himself by not living up to the terms of the Pact of Steel. He lamented to [his mistress, Clara] Petacci, in November 1939, “I have no time: I am in a great hurry. I won;t be able to carry out all that I had planned, I won;t be able. My world will be incomplete.”

Unlike with The Second Most Powerful Man in the World, O’Brien breaks no new ground in these pages; no reader familiar with the Second World War’s strategy or grand strategy will find any revelations here. But this author is adept at teasing the personal out of the informational, and the reader always benefits from this skill. His dictators in particular stand out in all their malevolent energy, although as O’Brien makes clear, some of the lessons they failed to learn are still eluding their malevolent modern-day counterparts. 

Steve Donoghue is a founding editor of Open Letters Monthly. His book criticism has appeared in The Washington Post, The American Conservative, The Spectator, The Wall Street Journal, The National, and the Daily Star. He has written regularly for The Boston Globe, the Vineyard Gazette, and the Christian Science Monitor and is the Books editor of Georgia’s Big Canoe News