Arsene Wenger always buckles and sells his best players - why will it be any different with Alexis Sanchez?

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It’s a situation that’s oh so familiar for Arsene Wenger but, far from that giving him the steady experience to weather the pressure, that past has arguably only increased that pressure. That is because the stark reality is that any time that the Arsenal manager has faced a situation like Manchester City’s interest in Alexis Sanchez he has always buckled. He has always caved.

It happened with Patrick Vieira, it happened with Thierry Henry, Emmanuel Adebayor, Samir Nasri, Cesc Fabregas and Robin van Persie and it is precisely why some close to the situation have more breezily been talking as if the same will happen again; that Wenger will eventually buckle again.

In each of those eventual sales, Wenger was as publicly resolute about refusing to let the player leave as he is now, insisting they just wouldn’t go.

That may have of course been a necessary negotiation stance for Arsenal at a time when things were financially tight after the stadium move but it also reflects the greater frustration for Wenger right now. Given how the club has grown since the sale of Van Persie in 2012 and financially moved on a level, these scenarios were supposed to be a thing of the past.

Instead, the Sanchez case only sharpens the still-bubbling debate over Wenger should now be part of the past; whether he should have taken the decision to leave after winning the FA Cup. The 67-year-old is a hugely proud man who is determined to prove such calls wrong, and obviously believes he can re-establish Arsenal as a title-challenging force again, but selling Sanchez would greatly diminish that - let alone the vibe around the Emirates.

It is why this decision takes on an even deeper dimension for Wenger than all the others, why it feels even more significant, more important - why whether he caves could be key to how his last contract goes.

One of the reasons that previous big sales were so frustrating was because of the feeling that they always seemed to delay Arsenal’s future, always affected a young project just as it was taking off but then the very fact they were young and Wenger was so committed to that plan meant that there was always time; always a chance to build again.

That will not quite be the case this time if this deal is to be Wenger’s last contract, although that is by no means certain. It’s just the footing of the club oddly isn’t as certain either: they have more disposable money than ever before, but so do their rivals, meaning that for the first time since Wenger joined they are no longer a certain Champions League club.

That feeds into the reality that there were always more justifications for sales in the past, more reasons beyond the potential negative effects of a want-away player staying. Henry was, for example, possibly becoming too dominant in the team; Wenger had doubts about Nasri; Van Persie was hitting 30; Fabregas was desperate to go home to Barcelona.

The only similar factor at play here is that Sanchez will himself turn 29 in December, but there is something else. When asked exactly why Wenger has given in before, some close to the transfers have even argued that the French manager can’t help ultimately “empathising” with the players, and can’t quite bring himself to keep them against their will when it comes right down to it.

Whether that it is fanciful or not, it would be in-keeping with the occasionally self-defeating purism we have seen throughout the Arsenal manager’s career; that refusal to compromise on seemingly core almost-moral football principles.

He just needs to refuse to compromise now in a different way. He needs to take a decision for himself. He needs to keep what could be his last team-group fully firing, to get back into the Champions League, so they can more easily replace Sanchez next season.

He is also very conscious of the actual economic factors surrounding all of this, and how it could be worth much more to keep the Chilean for another season than sell him for up to £80m now.

It’s then up to City to change that, to offer the kind of money that changes those economic factors.

Would Wenger cave then? It’s hard to say, but will say so much about what is to come - as well as those same decisions in the past.