I admit to being an occasional follower of Boris Johnson’s former Special Advisor. I’m not sure I would be at ease in his company, or he in mine, however. I have a sense that, stimulating brain though he may have, he is as likely to wreck a convivial dinner party as to make it. Described as one of the brightest of his generation, he graduated with a First in Ancient and Modern History from Exeter College, Oxford, in 1994 — a not-uncommon example of a member of the establishment biting the hand that feeds it.

I am reminded of another brilliant Oxford man, formerly of Jesus College, equally from an established background, who ended up questioning the existing order. Thomas Edward Lawrence specialised in Middle Eastern archaeology, then found himself wrapped up in a world war and espousing the cause of Arab nationalism, when such was not government policy. 

Iconoclasts who question the “brain fog” of the status quo are a necessary aspect of every progressive institution. They force organisations to take a hard look at themselves. It can even be a cleansing, constructive experience. General George S. Patton, that iconic American military figure, certainly thought so. His interactions with the US government and its military machine were frequently volcanic. He was one who delighted in “pushing wet spaghetti uphill”, if he thought it the right thing to do, once observing that, “If everyone in the room is thinking the same thing, then someone’s not thinking.”

Or we can take another member of Generation X (officially, mid-1960s to mid-1980s): Andrew Gilligan, three years older than Cummings and another historian, the product of St John’s College, Cambridge. A brilliant journalist, his relentless pursuit of the truth has often brought him into confrontation with the Government, notably over Iraq in 2003-4. Although he won awards for his journalism, some of his employers have been obliged to pay damages or issue corrections, when his zeal overstepped the mark. Though I have been on the receiving end of his uber-aggression, I would concede that his activities are necessary to a healthy, functioning democracy.

Cummings therefore is not unique, though his iconoclasm seems tattooed deep into his DNA. One of his former tutors at Oxford recounted in the New Statesman how he was always “fizzing with ideas, unconvinced by any received set of views about anything … something like a Robespierre — someone determined to bring down things that don’t work”. Perhaps it is no coincidence that both Cummings and Gilligan came to work for the Johnson administration in its early months. 

I cannot help feeling that Cummings is his own worst enemy, with his confrontational rather than collaborative public persona. Let’s take his own blog on Substack, for example. On 24 August he examined Professor Colin Gray’s thoughts on Strategy and Defence Planning.

I buckled up for Cummings’ own thoughts on strategy, of which he is a (self-advertised) master. My antennae started twitching at the first sentence: “Gray is one of the leading academics on ‘strategy’ since World War II.” The world renowned Colin S. Gray, an Anglo-American writer on geopolitics and professor of International Relations and Strategic Studies at the University of Reading, died in 2020. He left an impressive legacy of 30 books on military history and strategy, yet Cummings writes as if Gray were still alive.

But I quibble. Cummings agrees that “if one abstracts at the right level”, deep and recurring truths can be pulled from history. Few would contest his assertion that “how Rome innovated”, “how Rome organised military training” and “how Roman leaders connected political ends to military operations” are profound, timeless lessons.

Cummings seems blinded by his own time in Russia

My antennae soon twitched again. Mr Cummings infuses his writing with quotes from the 19th century Prussian military philosopher and general, Carl von Clausewitz, author of On War, published posthumously in 1832. He is equally adept at citing the much older Chinese general and philosopher, Sun Tzu, whose timeless work The Art of War dates to around 500 BC, and is lauded by military and business communities today. Both are eminently quotable and used by many leaders as a sort of magic wand to convey insight and wisdom. Cummings will not be the first or last to cherry-pick them, mining both for their aphorisms on anything to do with strategy and tactics, but often out of context for the period in which they wrote.

According to Cummings, Professor Gray (who spent his academic life studying strategy and advising national leaders) “warns that we can’t reliably predict crucial political ‘tipping points’, but he’s wrong. For example, Bayesian techniques, applied to polling/models, can and do predict critical tipping points in elections, which are inherently political, and therefore the root of strategy in Gray’s own formulation” (his italics). Bayesian probabilities evolve from the application of logic and statistics to a given problem. They are widely accepted and used in fields such as the mechanics of machine learning.

Cummings goes on: 

There are many similar examples, though obviously this entire field is massively under-rated in politics/government, because they’re so hard and so dysfunctional. This obviously does not negate the profound wisdom of [the] classics. It does not mean we should ignore ancient warnings to be humble in the face of inherent uncertainty, non-linearity and chance. But we can cautiously improve methods and know more of the future, at least in the relatively short-term (months, not decades), than a reasonable historian or scholar of strategy may think. We must always keep in mind the fragility of such predictions, the dangers of depending on them, and the need to seek strategies that are robust in many different plausible branching futures.

If I understand the Prime Minister’s former strategist correctly, he believes that the methodology used in predicting the outcomes of polls and elections, can be used in the wider international arena. That the vagaries of human nature, which result in diplomatic friends and enemies, in invasions and declarations of war, might be boiled down to statistical probabilities. Is Chancellor Scholz a Chamberlain to Putin’s Hitler? Is Zelensky a Churchill or a Dubček, the Czechoslovak leader who attempted reform before being overwhelmed by Soviet invasion in 1968? Gray is wrong, for the numbers will presumably tell us.

Cummings then wades into the war in Ukraine. This is apparently the point of his diatribe on strategy, which turns out not to be about strategy at all. It is here that Cummings reveals his true colours. “We have politicians pushing escalation with the world’s biggest nuclear power over a state, Ukraine, that is of trivial inherent importance to the world and which we are not obliged to fight for by any alliance.” He claims, “Our politicians have not described coherent ends for our action in Ukraine. ‘Putin must fail’ is not a coherent end. Truss’s definition of the end as ‘removing Russia from Crimea’ is a ticket to nuclear war.”

In fact, Cummings seems blinded by his own time in Russia (1994–1997), for nuclear war is not on the horizon. It never has been. It has been threatened on numerous occasions by Vladimir Putin, but not a single missile has been readied or put on heightened alert, despite the Russian leader’s frequent threats, or those of his minions, to the contrary. The war in Ukraine has proved that Russia is a military husk, whose hollowed-out centre, despite possessing overwhelming numbers of manpower and every category of military equipment, has been outclassed by a lesser-equipped opponent with superior willpower, doctrine and training. Presidents Zelensky and Biden understand this. So does Jens Stoltenberg, the NATO Secretary General and most of the alliance’s national leaders. However, it seems that Cummings is as intimidated by the illusion of Russian military power as the German Chancellor, Olaf Scholz. 

Cummings drags Clausewitz’s most famous dictum to his aid, that “War is not a mere act of policy but a true political instrument, a continuation of political activity by other means”. He is right to echo Clausewitz’s observation that “That the ends must be political”. Removing Russia from Ukraine seems to me a perfectly logical political end. Supplying Ukraine with military capability to achieve this, aligns perfectly with the political objective. Yet the thrust of the Cummings argument is that our politicians have failed to identify appropriate strategic objectives.

He overlooks the military teaching of Colin Gray and many others, that there are four levels of war. The tactical level is the short-term realm of skirmishes, engagements and battles. The operational level encompasses a series of campaigns (comprising many tactical actions) designed to win some larger objective. Most often undertaken by senior military commanders, the operational level looks further out in time and distance, sometimes lasting months. 

Then we have the military-strategic level, where admirals, generals and air marshals translate political direction into war plans and the allocation of resources at the highest levels. This in turn responds to the political-strategic level of war, where civilian governments decide whether or not to go to war, whom to fight, and with whom to ally. Decisions at this level involve the interrelationships between allies and national will. 

Russian success in Ukraine would act as a fatal lure

Cummings, the master strategist, in his haste to condemn this well-bedded institutional approach, has confused the military-strategic (the realm of generals) with the political-strategic (that of politicians). For the Western powers, political ends have always been analysed before military strategic planning begins. Although the intervention in Sierra Leone (2000-2001) taught that short-term military wins are possible, the lessons from Afghanistan and Iraq were that military and political exit strategies need to be in place before entry into a new theatre can be considered. The overthrow of Colonel Gaddafi in Libya (2011) was also a reminder that post-conflict peace building and stability operations were as important as the intervention of military forces in the first place. In other words, political ends must always dictate military activity.

As an aside, in his Substack piece, Cummings opines that “I also think many military experts have ignored the Godfather advice — never hate your enemies, it clouds your judgement — in their predictions of ‘Russian collapse’ and ‘Ukraine victory.’” I have not encountered any thinking of this nature with those who walk the corridors of power. This is precisely the point of the cool, reasoned judgement of those at the military and political-strategic levels. Perhaps Cummings is projecting his own hot-headedness onto others. 

After all, the mastermind of the 2016 Vote Leave campaign was renowned for his shoot-from-the-hip aggression, rather than a more ponderous, bureaucratic (but necessary) consideration of options. Running a successful political campaign that, several years on, seems at best a Pyrrhic victory, with half the nation alienated to the result, is unlikely to go down in history as a methodology to bury a contentious political issue for good. The aim of strategic thinking as taught by Sun Tzu and Clausewitz, is not victory at any price, but a triumph which lasts.

Finally, Cummings appears to throw any pretence of strategic thinking out of the window. He goes on to argue, “A ‘humanitarian’ logic makes no sense, given we routinely ignore such humanitarian logic applied to millions of blacks getting slaughtered in Africa for decade after decade. And our debate ignores the crucial political fact that in the east the war resembles a civil war, with both sides speaking Russian, layered on top of the history of some of the most appalling battlegrounds and massacres of the Eastern Front in World War II. Hence, partly, the depth of hate and the atrocities.”

This is precisely Putin-speak — that the Ukrainian conflict is essentially a civil war. In other words, let the Russians have it. The Cummings approach to strategy fails to see the consequences of unprovoked invasion by one sovereign state against another. How that would play out for the other former Warsaw Pact countries of Eastern Europe, and in other parts of the world where one neighbour looks aggressively at another. Never mind that Russian success in Ukraine would act as a fatal lure to the Russian leadership to extend their ambitions elsewhere.

My attention was drawn to a 2017 blog in which Cummings lauded the Sun Tzu approach: “You pull the opponent off balance with a series of disorienting moves, feints, bluffs, carrots, and sticks. You disorient them with speed … You try to make the opponent look like an unreasonable aggressor. You isolate them, you break their alliances and morale.” All well and good, but what that wise old Chinese philosopher was referring to here was the tactical and operational levels of war, the short-term business of winning battles and campaigns.

I shudder to think of the quality of “strategic advice” being bandied around No.10 at the height of the Cummings-Johnson partnership. Dominic may be a good blue-sky thinker, and heaven knows we need them, but his Substack article goes a long way in explaining what he is not — a strategic thinker.