Judgement is a valuable thing, particularly in politics. Sadly for Ed Miliband it’s a commodity he lacks.

Take the current farce over his endorsement of The Sun.

The photo to the right formed part of the newspaper’s biggest ever promotional campaign, in which they sent out 22 million free copies of a special edition right across England.

Awkward isn’t the word: the uncomfortable stare, as though he’s just noticed that the back page contains an embarrassing personal secret; the finger-tip grip, like someone holding a leash and trying to pretend the dog isn’t theirs as it fouls the pavement; the absurdity of the whole construct from a man who just a couple of weeks ago declared that he doesn’t read British newspapers.

Now, after a revolt from numerous Labour figures, including the Mayor of Liverpool, he has reportedly apologised, telling MPs privately that he is “very, very sorry” and publicly saying “sorry to those who feel offended”. It remains to be seen if the latter will be enough – the BBC-style non-apology, implying sorrow that someone feels bad, won’t necessarily wash.

The result is that he has annoyed both The Sun and its critics. Labour’s Icarus has been burned, and the plummeted into a nettle patch.

But who exactly did he expect to win over in the first place?

This is Ed Miliband, remember. He tried to make his name by backing Leveson, promising to break up Rupert Murdoch’s “empire” and accused the Government of a “cosy, sweetheart relationship with The Sun“. Labour have long claimed that one of his early successes was saying “what we all know and used to be afraid to say: News International was too powerful”.

His solutions – Leveson, state oversight of the media and so on – were the wrong ones, but it was at least an attempt to pick a side and target an audience. In a strategy-light Opposition it was a glimmer of a plan.

Few gains in politics come for free. The trade-off for chasing the votes of Hacked Off by slagging The Sun off is that you lose the votes of people who like the paper (or just the concept of a free press) – as with any political decision, the hope is that you win over more people than you lose.

What you can’t do is try to butter up both sides at once. Miliband is now finding this out.

Despite his Murdoch-bashing, Leveson-backing declarations, he has also desperately tried to develop the kind of “cosy, sweetheart relationship with The Sun” that he once denounced in the House of Commons. Yesterday’s photo was the most recent of several attempts at flirtation: he wrote for The Sun on Sunday in February, and took a ride with their official cabbie as part of the European election campaign.

The result is that he looks insincere to all sides. The backlash is, I suspect, just beginning.

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