What has already become the best-known anecdote in Jonathan Powell’s The New Machiavelli is a snippet of conversation he had with his then master, Tony Blair. Powell asked him how he could put up with having a three-hour conversation with Gordon Brown, to which Blair responded by asking him whether he had ever been in love. ‘“Not with a man”, I replied’ — and we know he was lying. This book is testimony to his devotion to Blair.

It is, for sure, a curious billet doux -– less like a bunch of roses than a handful of thorns. Comparing, however tangentially, your hero with Cesare Borgia -– the bully-boy who organised orgies to entertain his father, the Pope – could be viewed as the most back-handed of compliments. But the problem is more fundamental than that: it is Machiavelli himself. In trying to establish the reputation of his hero (and thus his own), Powell has to contend with the black legend that surrounds Old Nick.

He opens by announcing that ‘Machiavelli is much misunderstood’, which is akin to Diana Mitford recalling how amusing a chap was Hitler. Powell wants to insist that the author he emulates has unfairly gained opprobrium for telling things as they are, for straight-speaking, and for not blinking when being radical was what was needed. It sounds that Machiavelli was like how Powell wanted New Labour in power to be.

Yet, Powell’s use of Machiavelli hints at the depth of the problem. At one point, Powell declares that there are five qualities required in ‘a great leader’ -– number three being charisma, and the last (but certainly not the least) ‘charm’.

Powell divides sharply between those two terms: for charisma, he gives Weber the obligatory namecheck and means the aura which comes with assumed authority. For ‘charm’, he adds a supposed synonym: ‘sinuousness’. What precisely he has in mind is made clear when he goes on to bemoan that commentators see charm as ‘a sort of black magic’. What he is talking about is an ability to persuade that slides into the power to deceive. Machiavelli might have approved of the skill, but it is a mark of how Powell feels unable to be as blunt as his forerunner that he resorts to the comfort of euphemisms.

A generous response to Powell’s work would congratulate him for going further than the most popular Machiavellians and venturing beyond The Prince. He does lace his book with quotations from Machiavelli’s more substantial Discourses on the First Decade of Livy. It is The Prince, though, that provides the ordering principle to Powell’s book and there is no hint that the author sees any inconsistencies between Machiavelli’s best-known works.

Indeed, he sees neither inconsistency nor irony. Early on, writing ‘in defence of Machiavelli’, he rolls off a list of quotations of authors who have praised The Prince. He includes Rousseau who, as Powell says, described the little work as ‘the book of republicans’, but the phrase is taken out of context. As is explained in The Social Contract, Rousseau saw Machiavelli as hiding his true meaning for fear of Medici reprisals, while revealing his intention to those who had ears to hear by the choice of Borgia as ‘his detestable hero’. There is a long history to reading of The Prince as disingenuous or ironic; Powell, in taking the book at face value, fails to grapple with how sly Machiavelli might actually have been.

Why, then, does Powell make so much of his use of Machiavelli? He says at the outset that he does not want his book to be ‘another memoir of the Blair years’ – though, in that, he fails.

It is perhaps the fate of all who have once negotiated power, that they later find that they themselves have become otiose and so hark back to their past, like Scipio and Hannibal discussing their martial merits in retirement. Powell cannot completely rise above the need to settle scores: to begin the rehabilitation of Blair, and to help unravel whatever good repute Gordon Brown might have. He strains to give his personal emotions an intellectual justification -– not to mention a wider relevance (otherwise known as selling power) -– by ordering his recollection not by date but by an analysis that takes as its starting-point The Prince.

The result, though, reads as oddly disappointed: he served the most successful Labour leader in history but his book exudes the chagrin of hindsight. He seems to wish that the government in which he worked had been leaner -– and much meaner. At heart, his message is that, whatever dark arts it mastered, New Labour was not Machiavellian enough.

There is another insight that drives his use of his source: his belief that a prime minister is not so distant from a Renaissance prince as is usually imagined. A PM is necessarily surrounded by a court in which sage advice can all too easily be drowned out by the yes-men, the flatterers. He also does not have a monopoly of power, which is, instead, dispersed among the cabinet ministers, whom Powell depicts as ‘feudal barons’.

Potentially interesting points, but ones for which Powell might have been helped if he had raised his eyes up from The Prince and looked at some other works: Thomas More or John of Salisbury are more outspoken than Machiavelli about the vicious circle of court life, and any comparison of too-powerful ministers with medieval nobles could have taken as its starting-point the chapter on ‘overmighty subjects’ in John Fortescue. But, then again, The New Fortescue would not have made as catchy a title.

What Powell clearly relishes in Machiavelli is his ability to draw out a general truth from the examples he deploys. He attempts to emulate that, peppering his work with dicta, usually opened by ‘a prudent leader’ or ‘a wise prime minister’.

But some of Powell’s dicta would have left Machiavelli shaking his head. To give just one example: Powell’s advice is driven by a simple dichotomy between a ‘strong’ and a ‘weak’ leader (where, for weak, read Brown). Yet, Machiavelli, particularly in The Discourses, had a keen sense of how circumstances can define the right path: in other words, strength and weakness are not simply born of innate qualities or learnt skills, they also change with the context. The key virtue for Machiavelli was prudence, but not in the way that Powell would have it. As with New Labour, what’s ‘new’ is not necessarily better.

Other insights would have had Machiavelli scratching his scalp. Powell was so intimately involved in the minutiae of running Number 10 that he cannot but want to reform the mechanisms of central government and he has some detailed prescriptions for that. At the same time, they reduce the work’s ambitions to the very local.

Powell mentions once Francesco Guicciardini, most famous for sharing with his lower-born contemporary, Machiavelli, a sharp cynicism about politics, expressed in his histories. Guicciardini also wrote a Dialogue on the Government of Florence which delved into the details of the how to overhaul the instruments of rule in his city. The impression left from reading this book is that Powell wants to emulate Machiavelli but he ends up being more like Guicciardini.

* David Rundle is a Liberal Democrat councillor in Oxford, who blogs on politics at de moribus liberalibus and on Renaissance history at bonæ litteræ.