The death of Derek Draper, the former Labour party apparatchik, got acres of press coverage, with tributes pouring in from the great and the good, including Tony Blair. But reading the obituaries, I couldn’t help feel that they didn’t do justice to the man I first met in the early 1990s, and for a time counted among my closest friends. They neither captured the full extent of his skulduggery nor how entertaining he could be when relating the latest gossip from Blair’s inner circle.

His friend Decca Aitkenhead’s piece in the Sunday Times came closest, but she left out one of my favourite anecdotes, perhaps because it involves her. As I recall, Derek’s wife, the TV presenter Kate Garraway, had sold a package to OK! magazine about their wedding in 2005 and, as part of the deal, agreed to write an account of her ‘special day’. It was due while they were on their honeymoon and, since selling the story had been Derek’s idea, she asked him to ghost-write it for her. He agreed, and then, unbeknownst to her, called Decca and asked if she would do the honours. When the piece was published  under Garraway’s byline, Decca was astonished to discover that Derek hadn’t changed a single word in her ghost-written, ‘first person’ article.

There was no trace of hypocrisy with Derek – he would describe his intrigues with the relish of a Shakespearean villain

I like that story because of the layer upon layer of duplicity it reveals, which was typical of the man. I also find the brazen cynicism of it quite appealing. That, too, was one of Derek’s hallmarks. During the time I knew him well, from 1993-95, he was unapologetic about being a rogue, bragging about his misdeeds as a Labour party fixer as he held court in Green Street, a nefarious private members’ club in Mayfair. I remember asking him at the end of one long evening whether he had a contingency plan if any of his misdemeanours were written about in a newspaper. ‘That’s easy,’ he said in his strong Lancashire accent. ‘Born-again Christian.’

I later had to remind him of this conversation when, following his downfall after the Observer ran a devastating exposé in 1998, he earnestly told me he’d seen the error of his ways and become a born-again Christian.

He and I were unlikely friends, given our diametrically opposed political views. We met through a mutual acquaintance – Charlotte Raven, whom I’d hired to work as an associate editor on the Modern Review. They’d met at Manchester University a few years earlier and still slept with each other from time to time, though they were really just friends. Derek was working for Peter Mandelson and used to describe himself as ‘the spin-doctor’s spin-doctor’, but he was more of a backroom operator – Labour’s equivalent of a Nixon burglar. Unlike other political hacks, there was no trace of hypocrisy with Derek – he would describe his intrigues with the candour and relish of a Shakespearean villain.

Which, of course, meant he was bound to come unstuck. He was mendacious, but not so mendacious that he would try to deceive his friends about what he got up to. At the launch party of Blair’s 100 Days, a book he’d just published about New Labour’s first 100 days in office, a lobby correspondent asked whether the rumours were true that he hadn’t actually written it. ‘Written it?’ he replied. ‘I haven’t even read it.’

After his first fall from grace – there were several – he went to America to retrain as a psychotherapist, and I visited him in California while I was on tour to promote How to Lose Friends & Alienate People. This was in 2002 and he claimed to be a reformed character. I was sceptical, telling him that the dark arts he’d learnt at the feet of Mandelson would prove too tempting to renounce for ever. Sure enough, after his return to London, he was lured back to work for the Labour party, whereupon he quickly got caught up in another scandal, this one involving Gordon Brown’s spin-doctor Damian McBride. They had planned to use a blog they’d set up to disseminate scurrilous gossip about leading Conservative politicians, including David Cameron, until they were exposed by Guido Fawkes.

Lesser men would have been defeated by being repeatedly disgraced, but there was something so winsome about Derek – deep down, he just wanted to be loved – that he found redemption in the arms of Garroway. His friends couldn’t believe it when they heard of his engagement – Piers Morgan said: ‘If I’d known the bar was so low, I would have had a go myself.’ But it turned out to be a successful marriage and ‘Dolly’ couldn’t have hoped for a more devoted carer when he was laid low by Covid. I will miss the old rascal.