Listen to the full interview via the podcast
Just four months ago we spoke to Simon Kuper about Milan freshening up the management by hiring former player Clarence Seedorf.
Yet now the Dutchman appears on the brink of getting the sack with his former team-mate Filippo Inzaghi set to take the step up from managing the youth side.
But what has gone wrong for Seedorf at Milan and is Inzaghi the right man to take on a club that currently lacks financial might?
To answer that we spoke to James Horncastle who told us that issues arose between Seedorf and his bosses.
"The club have other ideas and while he can point to getting good results - 35 points in half a season which would be worth fourth place over a full season - he feels as if he should be in the job. But it's not results that only count in this job. It's relationships between Seedorf and people in the hierarchy," said Horncastle.
The planning of training sessions was also another issue which Horncastle also detailed, as well as divisions between Seedorf and Adriano Galliani who had originally favoured giving the job to Filippo Inzaghi.
But one issue for Milan highlighted by Horncastle, who do not have too much cash to spare, is the large payout Seeford is now entitled to.
"I think this is one of the reasons why they have gone for Inzaghi because he works for the senior youth team. They can just promote him. He's a low cost appointment unlike some of the other people they were reportedly interested in."
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