Arsene Wenger has long been known as a shrewd operator in the transfer market. The Arsenal boss has nurtured a string of young talent during his decade in charge, however, recently there have been signs that all is not well at the club for whom the Frenchman has brought unprecedented success.
His failure to persuade fellow countryman Mathieu Flamini to remain in London will add fuel to the fire for those critics who have already began to question whether Wenger's philosophy is reaping the kinds of rewards expected.
Indeed, without a trophy in three years, the sight of one of their players of the season heading for Milan is a worrying prospect for many supporters and has the potential to spark other players' departures.
Flamini's industrious work alongside Cesc Fabregas in the heart of midfield has been heralded through the current campaign, but the Frenchman has history when it comes to issues of loyalty. Wenger himself poached the 24-year-old from Marseille on a free transfer after he had agreed terms on a contract renewal, prompting Marseille coach Jose Anigo to describe him as a 'traitor'.
What goes around, comes around and Wenger, usually a canny operator when it comes to tying his stars down, lost out - choosing to criticise his former charge for 'holding the club to ransom' instead of taking it with quiet dignity.
It seems strange that a club who are making more money than ever from their new 60,000 seater stadium have such an aversion to breaking their wage structure for their most important players. Granted, structures are there for a reason, but the likes of AC Milan and Chelsea will always be able to offer players astronomical sums to move clubs and if Arsenal can't keep pace then this situation will continue to arise.
It may not be right, but the majority of top flight professionals will still choose a massive pay packet over loyalty to a particular club. Football is all about money and Wenger's pursuit of 'the beautiful game', while it can be commended for its vision on and off the pitch, will come a close second when reality rears its ugly head.
Indeed it looks as though Wenger will lose another of his stars, with winger Alexsander Hleb's agent claiming that he will leave the club in the summer. Inter Milan seems his most likely destination and, while Hleb hasn't contributed goals to the extent of a Freddie Ljungberg or Robert Pires, the Belarussian is another talented player that the club can ill-afford to lose.
Flamini's departure can be put down to money, as his history suggests; but Hleb's may mean more in the context of the club's decline in recent years. If Wenger is unable to persuade the likes of Hleb to stay, then there is scope to suggest that some other players may also seek their fortunes elsewhere.
One of those continually linked with a return to Spain is Cesc Fabregas, although Wenger can be safe in the knowledge that his midfield prodigy is far more loyal to the Arsenal cause than either Flamini or Hleb.
Indeed, the youngster signed one of the longest contracts in history last year and has long proclaimed his admiration for his boss. With Barcelona and Real Madrid sniffing around the threat of Fabregas leaving is an ever-present, but with one of his best seasons behind him, the 20-year-old is the antithesis of the mercenary culture of modern day stars.
Building his team around Fabregas, Wenger now needs to spend money to contend with Man Utd and Chelsea and lift some of the morale that a third trophyless season has sapped from the supporters.
Links with Man City's Michael Johnson and Villa skipper Gareth Barry suggest that Wenger will look to replace those who decide to jump ship this summer and only a fool would question his ability to unearth a new young talent, but the Frenchman has always been loathe to spend big on established stars. And that is what the clubs needs now.
Having turned down the chance to sign Fernando Torres, Cristiano Ronaldo and Wayne Rooney because of the size of their transfer fees, Wenger has been burned before when splashing the cash. £10million on Francis Jeffers, £6million on Richard Wright and what turned out to be around £13million on Jose Antonio Reyes spring immediately to mind. Wenger has been wary ever since.
The club has dealt well with departures before: when Patrick Vieira left it gave Fabregas a chance to shine, likewise Emmanuel Adebayor has blossomed after coming out of the shadow of Thierry Henry. Yet, having to plug the gaps coming from unexpected departures this summer, Wenger may be blinded by the fact that his squad needs more strength in depth.
Wenger's assertion that 'if we'd won at Man Utd we'd have won the title', is either a clever smokescreen for his own inability to compensate for the injuries to Eduardo, Robin Van Persie and Bacary Sagna, or a symptom of a delusion that his philosophy is working as well as ever. One hopes, for Arsenal's sake, that it is the former; but his decision to play the impulsive Emmanuel Eboue on the right-wing for most of the season suggests otherwise.
Eboue had a stunning season at right-back before the arrival of Bacary Sagna, yet he is sorely out of his depth on the wing - never once looking like he'd provide a telling cross or even score a goal. Indeed Wenger's blind faith in the Ivorian, coupled with the sale of Lassana Diarra to Portsmouth in January, can be seen as a major contributing factor to their dwindling title challenge.
With an injury to the impressive Sagna coming in the club's most crucial run of games, Wenger's decision to shift Kolo Toure to right-back upset the balance of the side and exposed a startling lack of depth. Diarra could have filled in and would have also taken over the mantle from Flamini in central midfield, but chose to join the Redknapp revolution instead.
Sticking rigourously to his guns Wenger believes his side are strong enough, even in the wake of Flamini's exit. The Frenchman seems to have unearthed another talented youngster in Cameroonian Alex Song, but experience is needed in the spine of the team if Arsenal are to stiffen their defensive resolve.
The likes of Philippe Senderos, Denilson, Abou Diaby, Justin Hoyte, Armand Traore and Niklas Bendtner have not suggested that they have enough to cover any major absences over the course of a season and certainly don't match up when you compare them with Manchester United and Chelsea's fringe players; while Wenger also faces a tough decision over his captain.
After William Gallas' petulant display after the Birmingham game, a change is surely due. Gallas won't take it well, but Fabregas or Kolo Toure are far better suited to the role and if Wenger keeps faith with the French defender (as he did with Thierry Henry last season), then he is doing more harm than good.
Die-hard fans will point to the fact that Arsenal were flying high at the top of the league for the first half of the season as a reason not to change anything. Yet over the past few years, the club have started brightly and then vanished without a trace once injuries and fixture congestion takes its toll in the latter stages.
This season has been no different and, coupled with a few strange decisions by the usually unflappable Wenger, Arsenal do not look capable of challenging United and Chelsea on all fronts without comprehensively adding to their squad in the summer.
In failing to persuade Flamini or Hleb to stay at the club, Arsenal have shown a weakness which their rivals are likely to capitalise on. Without an injection of new blood at the club, another trophyless season seems an inevitability although Wenger's own position is unquestioned. The manager can breathe new life into the club once again with a set of fresh faces; but his first job is to persuade his current crop of stars to stay and the signs don't look good.