Tying his future to the long-term success of Theo Walcott, will be the biggest gamble of Arsene Wenger's Arsenal career. Rumours have surfaced today that Walcott is poised to finally sign a new contract after months of wrangling.
Espn.co.uk reports that Walcott has agreed a new three-and-a-half year contract. Official confirmation is still pending. Although the move will be seen as a boost to Arsenal's inconsistent season, it also represents a major risk from Wenger.
The first possible hazard is Walcott's own inconsistencies. This is a player who has endured a stuttered development, since joining the Gunners as a highly prized teenage in January, 2006. Walcott has rarely been able to consistently showcase the talent to match his potential.
Part of the problem has been effort. Too often Walcott has appeared content to drift in and out of games. He has sought refuge in complaints about his place on the wing and publically lobbied for a move to central striker.
As he so often does, Wenger is choosing to believe in the character of his player. He is opting to trust that Walcott will repay the club's faith, represented by fiscal reward, with renewed effort. However, the flip side is a player who has finally forced through his monetary demands, now slipping back into bad habits.
The new deal means the bare minimum is no longer an option for Walcott, or his under-fire manager. It's that same pressure on Wenger that pervades every potential implication of Walcott's new contract.
Returning to the positional debate clarifies this issue. The argument about whether Walcott belongs on the wing or through the middle, is as contentious among Arsenal fans, as it has clearly been around the negotiating table.
This season Wenger has ceded to Walcott's insistence that he can be an elite central striker. The experiment has offered no definitive answers. Impressive performances against Reading, Wigan and Newcastle United, have been countered by inept performances against Southampton and Manchester City.
Of course, Wenger's fine history of turning wingers into strikers offers hope about Walcott's future in the middle. After all, he did it with Thierry Henry and Robin van Persie. However, the real question is, does Wenger have the time for one more transition of this type?
Patience is in short supply among many Arsenal fans. Seven seasons and counting without a trophy can do that to a fan base. Many sections of the Gunners support want ready-made stars over the promise of potential.
Walcott symbolises that wait for potential and all the frustrations that can accompany it. His 14 goals, improved finishing and movement this season, show a player who can be a threat anywhere along the forward line. Yet will he let position and effort stop him? At a supposed £90,000 per week, according to The Independent, Wenger had better hope he doesn't.
Perhaps the Frenchman's biggest gamble with Walcott has been prioritising his deal during the January transfer window. With their top four status under arguably its greatest threat, few would deny that Arsenal should use the winter buying period to recruit new faces.
Yet Wenger has continually stated that Walcott's deal must come first. Once it's signed, will it be the pinnacle of Arsenal's transfer dealings this month? If so then Wenger should expect a torrent of abuse from a frustrated support, at the first sign of trouble.
If he does prioritise existing resources over spending to reinforce, Wenger will further alienate those who believe his time is up. More importantly, he will also risk driving away the moderates who hope for improved results, but recognise the difficult circumstances the manager has faced since moving stadiums.
Without that support, Wenger would cut an increasingly isolated figure at the club, especially if Arsenal continue to struggle in the English Premier League. By making Walcott the primary focus of his transfer dealings, Wenger has played a dangerous game with the expectation and tolerance of his own fans.
Walcott can be Arsenal's match-winner, just as easily as he could join the ranks of flops like Jose Antonio Reyes and Aleksandr Hleb. His career crossroads mirrors that of his manager.
Wenger has banked everything on the belief that Walcott is finally ready to emerge as his latest prospect-turned world class performer. Even for a risk taker like Wenger, that's a brave gamble.