Shy he may be, but Gordon Brown is a formidable networker. Among the unlikely alliances he has formed is one with Paul Dacre, editor-in-chief of the Daily Mail and one of Labour's most feared critics.
Mr Brown's allies say that Dacre began the courtship around 2000 after growing disillusioned with the first Blair premiership. At first he was treated warily.
Dacre is said to see the new prime minister as a kindred spirit: hard working, high-minded, scornful of the metropolitan elite and personal celebrity, a leader touched with potential greatness.
Though his newspapers regularly attack the chancellor on issues such as tax and pensions, they never do so with the ferocity reserved for Mr Blair and his acolytes. So when the Daily Mail serialised Tom Bower's hostile biography of Mr Brown in 2004 the extracts chosen were - almost uniquely - mild rather than sensational. News International papers, notably the Sun, have been much harder on the chancellor.
If Brown can keep the Daily Mail and the Associated stable onside until the next election, it will be a remarkable feat. The two occasionally have breakfast. But more often Dacre will head to No 11 for early evening drinks, returning to the Mail's west London HQ, sometimes invigorated, sometimes frustrated. He returned the favour with lunches the newspaper's offices.
Dacre has taken an interest in children's charities at the chancellor's behest. And some Whitehall officials referred to the Treasury's tax on internet gambling as their "Dacre tax".
Many Labour loyalists are astonished that such a relationship should exist between the puritanical Scot and the ferocious Tory who claims to know and shape what Middle Britain thinks.
But insiders at the Treasury and Fleet Street are adamant that the link is based on mutual respect. Dacre was invited to the funeral of the Brown's baby, Jennifer Jane, who died in January 2002.
"It's not a love-in. They have passionate debates about particular subjects, like grammar schools. What they both enjoy is the rough and tumble," said one Brown adviser.
Old hands at the Mail confirm that their boss, who does not like London or the "metrosexual elite", sees Mr Brown as an intelligent, well-read and serious exception to the political pygmies around him. "Against his better instincts Dacre sees Brown as a genuinely special politician, the only one around who is touched with the mantle of greatness," said a journalist who knows both men.
A less flattering assessment is that both men are outsiders, able but prone to insecurities which manifest themselves in bullying. "Neither is comfortable in his own skin," said one. "They're friendly, but there's some opportunism in it too," said another.
It helps that Dacre quickly lost any regard for Mr Blair, whose conference attack on the "forces of conservatism" holding Britain back in 1999 had been an earlier turning point.
Brown strategists hope for what they call "a fair hearing" from the Mail group, but admit that Dacre is always "on the verge of disappointment with Gordon". Events could unfold either way, they suggest. The Brown camp is aware that David Blunkett's courtship of the Mail and Sun did not spare him their ruthless attacks over his affair with Kimberley Fortier: Dacre believes the story comes first.
One aide warned: "Gordon won't waste time trying to persuade the Mail to support Labour." But some Mail writers believe Mr Brown has one tempting bauble in his pocket. Dacre, 60 in November next year, has had his contract extended. But they suspect he'd love to retire with that knighthood.