The former is Boris Johnson’s senior advisor and de facto chief staff; the latter is Jeremy Corbyn’s communications and strategy director. One is hard-right, the other hard-left.
Both are formidable operators behind the scenes – unelected advisers widely suspected of pulling the strings of their political masters.
Their take on the world is very different and their politics could hardly be further apart. But they’ve a lot in common. Both are Oxford graduates who went to posh public schools: Winchester and Balliol College (Milne), Durham School and Exeter College (Cummings). And both of them want to disrupt and smash the status quo.
Both have a connection with Russia. For three years in the 1990s, following the collapse of the Soviet Union, Cummings worked there; exactly what he did is unclear.
Milne has been an apologist for Soviet communism and for Putin, expressing understanding of Russian military action in Ukraine and the annexation of Crimea.
Cummings, once described by David Cameron as a “career psychopath”, is a ruthless operator, with a deliberately confrontational style, who believes in breaking the rules if that’s what it takes to win.
Milne’s sobriquet is “Jeremy Corbyn’s brains” or, more sinisterly, “Corbyn’s Beria” – after Stalin’s feared secret police chief. In stark contrast to Cummings, he is known for his charm, but there is steel behind the charm. He has a remarkably low profile and a much quieter, though no less effective, style.
How did they get where they are today? From 2011-2014, Cummings was a controversial aide to Education Secretary Michael Gove. “The atmosphere he created was one of fear,” said one former colleague, while a member of the No 10 Policy Unit remembered him as “awkward, abrupt, arrogant, aggressive”. His moods were variable.
In October 2015, Cummings became campaign director of Vote Leave. He is credited with inventing the “take back control” mantra – and that notorious £350m slogan on the Brexit bus.
Last year Vote Leave was fined £61,000 for breaking electoral law on spending limits. Earlier this year Cummings failed to give oral evidence to the Digital, Culture, Media and Sport Select Committee’s investigation into fake news – MPs unanimously found him to be in contempt of Parliament.
After becoming the Prime Minister’s chief of staff, he reportedly told special advisers that the government’s mission was to take Britain out of the EU by October 31 “by any means necessary”. That helps to explain Johnson’s unlawful prorogation of parliament.
“When are you ******* MPs going to realise we are leaving on October 31? We are going to purge you,” the Mail reported Cummings as screaming at former Business Secretary Greg Clark.
Johnson duly purged not only Clark, but two former Chancellors of the Exchequer, Winston Churchill’s grandson and 18 other Conservative MPs who had dared to delay the October 31 deadline in order to avoid a no deal exit from the EU.
Now let’s look at Milne. Before taking up his post with Corbyn, he had a long career at The Guardian. Beginning as a news reporter, he became Comment Editor and then Associate Editor. Three years after the 9/11 terrorist attack on New York, he controversially ran a column by Osama bin Laden, assembled from recordings of one of his speeches. He is a longstanding supporter of the Palestinian cause.
According to The Guardian’s former Middle East editor, Brian Whitaker, Milne views international politics almost entirely through an anti-imperialist lens. He has been a fierce critic of the EU and he has given press briefings in contradiction of statements made by Sir Keir Starmer and Emily Thornberry, senior members of the Shadow Cabinet.
According to the recent Channel Four Dispatches documentary, in the summer Corbyn had been persuaded (by John McDonnell and Diane Abbott) to adopt a more pro-EU Remain stance, but changed his mind following an intervention by Milne.
Neither Corbyn nor Johnson are known for their mastery of policy detail. That’s a gap that Milne and Cummings, in their very different ways, have been happy to fill.
Johnson and Cummings, with their Brexit supporters, have pretended to defend Parliamentary sovereignty while doing everything they can to subvert it.
If there’s a Labour government, might Corbyn and Milne, with their far-left supporters, be tempted to follow suit? Whoever ends up as Prime Minister after December 12 (assuming that’s either Johnson or Corbyn) will have a dangerous accomplice at his elbow.
Tony Rossiter is a former civil servant. He lives in North Yorkshire.