Manchester United contract woes prove gap to City is far wider than just points

As Manchester City stand on the verge of tying down the future of English football's brightest prospect, Manchester United remain at a stalemate with David de Gea.

This is yet another area where the blue half of the city is blazing a trail, while the red side languishes behind.

Discussions are ongoing with De Gea's representatives over a new five-year deal, while Anthony Martial is also negotiating a long-term contract.

United are confident Martial will sign on the dotted line soon – but De Gea is more of a concern, with his ambitions to win major trophies believed to be the major stumbling block.

Selling City's stars on the promise of silverware has been an easy pitch for director of football Txiki Begiristain, who has secured the futures of one key player after another over the past 12 months.

Raheem Sterling – on a deal that could be worth as much as £300,000-a-week – became the latest of Pep Guardiola's stars to commit himself to the Etihad last week, signing on for another five years.

Add his name to those of Kevin de Bruyne, David Silva, Sergio Aguero, Ederson, Gabriel Jesus, Fernandinho and Nicolas Otamendi as City have systematically snuffed out any doubt about the players who were so pivotal to last season's Premier League title triumph.

Leroy Sane is next on Begiristain's to do list after Phil Foden completes the formalities of his new six-year contract.

There is little chance of Guardiola's squad being broken up any time soon, which serves as a major worry for their Premier League rivals and a boost to their ambitions of conquering Europe.

It is a testament to the organisation of the club's football department, which works seamlessly through chairman Khaldoon al Mubarak, chief executive Ferran Soriano, Begiristain and Guardiola.

Compare that then to Old Trafford, where Luke Shaw was in danger of walking away as a free agent in the summer after his contract was allowed to drift into its final 12 months.

The England international became one of the highest paid defenders in the world when signing a five-year deal last month, but there were real fears United would lose him for nothing.

The same applies to De Gea and Martial.

United can protect their assets by triggering 12 month options on the pair, which will keep them for one more year after this – but if the offers on the table are not signed by the summer, they will seriously have to consider cashing in before the start of next season.

It is becoming an all-too familiar story.

Marouane Fellaini had one foot out the door before United backed down and handed the Belgian a two-year deal with the option of a third.

United had their misgivings about the size of the deal, despite Jose Mourinho lobbying hard for the midfielder.

Now they face similar scenarios with Juan Mata, Ander Herrera and Ashley Young.

All three can speak to clubs abroad from January – and all three present United with the dilemma of losing saleable assets for nothing or committing themselves to expensive contracts for ageing and/or fringe players.

If 33-year-old Young can be convinced to sign a 12-month extension, it makes sense, considering his versatility and experience.

The cases of Mata and Herrera are more complicated.

Mata, who will turn 31 before the end of the season, knows he is about to sign the last major contract of his career.

His form in recent weeks is evidence of his value to United, while Mourinho has made it clear to United's board that he wants both Mata and Herrera to stay due to their contribution to the dressing room.

But Mata is not regarded as part of Mourinho's strongest XI – and should the manager be given the funds to sign a right winger in January or the end of the season, the Spaniard will be pushed further down the pecking order.

On a two or three-year contract on around £130,000-a-week, he will become a very expensive squad player.

Likewise Herrera – who, at 29 – would be committing himself into his thirties.

In the cases of all three, United have almost certainly missed the boat in terms of cashing in. That needed to be done in the summer when they had a full 12 months to run on their deals.

By signing them up to new long-term deals, they would be leaving even less space for Mourinho – or his successor – to overhaul a squad desperately in need of freshening up.

Mourinho, himself, spent his first two years at the club clearing out many of the players he inherited from Louis van Gaal, in particular.

He believed he was left at least two players short in his rebuilding plans last summer – and hopes to address that in January with the signing of a top class centre back and possibly a right winger too.

But with United already saddled with a wage bill of over £300m-a-year, something has to give.

Not for the first time, the need for a director of football is highlighted.

Begiristain's long-term planning, which pre-dates Guardiola, has left City with beautifully balanced squad on and off the pitch.

A focused approach allows them to identify and secure transfer targets in advance, at the same time as securing the futures of their existing players.

United, meanwhile, are caught between games of high stakes poker with star players, while also trying to meet their manager's transfer demands.

Ahead of another window when Mourinho hopes to strengthen, United's hierarchy look likely to have their hands full just trying to keep hold of what they've got.