Last month, the publication of the Prime Minister’s EU renegotiation aims fell rather flat on Fleet Street. The centre right press were underwhelmed at best, and as I wrote at the time:

‘Cameron has just handed the Outists a huge opportunity. His pitch has not only failed to win over the centre right press, it seems it has actively repelled some of them. The ball is now in Vote Leave’s court – can they succeed in winning hearts and minds on Fleet Street where he has failed?’

The Daily Mail has now provided the first answer to that question: yes, the Leave campaign can and will capitalise on the weakness of the Government’s pitch. On Wednesday the paper urged the Prime Minister himself to support a vote to leave – arguing that ‘withdrawing is the only way we will ever control mass immigration into this country.’

Newspaper support isn’t everything, but this is a hugely significant development. The Remain camp hope to paint their opponents as a fringe, distant from the mainstream life of the nation – that will be harder to do with the second-most read newspaper in the country advocating a Leave vote.

The timing makes it all the more significant. The Government would like to hold a public row with the EU, secure some small change to the rules on welfare for migrants and then parade such an agreement as a victory. The Mail has effectively declared that the demand for EU welfare changes is without value, and that even if achieved it would be insufficient to make a Remain vote worthwhile – the strategy is holed beneath the waterline.

Notably, while The Sun is yet to back one side or the other, Wednesday’s The Sun Says editorial was also dismissive of the value of Cameron’s welfare demands. With weak demands, a disorganised renegotiation campaign and an EU utterly unwilling to make fundamental, lasting changes, more of Fleet Street could well come to recommend a Leave vote.