It has not aged well, to say the least.
From Barnard Castle to the Brexit bus, here’s a rundown of career “highlights” of Boris Johnson’s former top adviser.
Bernard Jenkin tells prime minister to ditch "hangers on" in his top team.
No.10 refuses to deny PM’s partner Carrie Symonds is unhappy about the job offer.
The Conservative Party is investigating Theodora Dickinson, who also used to work for Vote Leave, after the slur towards Bradford-born Naz Shah (pictured).
Conservative and pro-Brexit voters are turning against the prime minister after he refused to sack his chief adviser.
Ex-special advisor James Starkie, who worked with Cummings for Vote Leave, said he would be "shocked" if the aide leaves No.10 in the next few months.
But the former Vote Leave boss is not Downing Street's top earner – some advisers make almost as much as the PM himself.
Parliament has ignored warnings on fake news for 2 years and now democracy is at stake, DCMS Select Committee member Ian Lucas writes.
As David Cameron renews his feud with the former Vote Leave chief, a fresh battle looms over just who should run the Tory campaign.