Jose Mourinho faces one of the toughest challenges of his managerial career so far this summer.
After a torrid campaign last term, Tottenham Hotspur have been left to pick up the pieces.
Despite rallying to finish in the Premier League's top six, the north London side are in need of a summer rebuild as they prepare to go again next term.
After several seasons of playing in the Champions League, to be gearing up for a campaign in the Europa League is a bitter blow - and one which they won't want to replicate again.
That means that strengthening the squad ahead of the new season is a must.
Adding new players is clearly a big task, but it could also be difficult to fend off interest for their more talented players.
Reports last week suggested that Manchester City could be lining up a move for Harry Winks, with Pep Guardiola said to be 'intrigued' at the opportunity to develop the midfielder.
While a fee of £40million is touted for a potential move, former Spurs striker Darren Bent believes that Winks would really excel at the Etihad Stadium.
Speaking to Football Insider, Bent said: "It could help him improve as a player, the way Manchester City play, he’s a great link player and is really talented – in possession we’ve seen how he protects the back-four, how he can move the ball around.
“I think he’d be a great addition for Manchester City.
We don’t know what the price will be, he’s a talented footballer and I think one, Spurs won’t want to let him go and two, he would be an excellent addition, something slightly different to Manchester City.”
GIVEMESPORT'S Phil Spencer says...
This would be one of the deals of the summer if it was to come off.
Harry Winks is clearly a talented player, but I never had him down as someone who was good enough to play for Manchester City.
The 24-year-old is certainly technically-gifted and fits the mould of Pep Guardiola's side, but I really struggle to see where he fits into that midfield at the Etihad Stadium.
Unless Spurs were really looking to cash in, it's not one that I see being a priority for Guardiola.
However that's not to say that Winks won't attract attention.
With Tottenham not competing in the Champions League it could difficult to keep certain players happy, and if a bigger club were to come knocking, it would be nearly impossible to turn them away.
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