This long read piece in the New Statesman tells one almost more than one needs to know about Dominic Cummings and his intellectual formation. Two things stand out: that at Oxford, he was a pupil of Norman Stone, who was a clever, radical Tory anarchist, who was also a well-known drunk, which could perhaps help to explain Cummings’ tendency to wander round the Commons with a glass in his hand and always arrive at work so late and so disheveled. The second thing is the amount of time he spent in Russia in the mid-1990s, where he will have witnessed at first hand and perhaps enjoyed the breakdown of civil society and the way it could benefit a small number of oligarchs who later helped to bankroll his Vote Leave campaign. Clever, undoubtedly, but corrupt as well.

https://www.newstatesman.com/politics/uk/2019/09/dominic-cummings-machiavel-downing-street