The last year of his Arsenal contract, no Premier League title for 12 years, growing calls from impatient fans for him to leave. It really is crunch time for Arsene Wenger.
But the Frenchman is not the only man facing a crucial campaign at the Emirates Stadium. Alex Oxlade-Chamberlain enters his sixth season with the Gunners and fans are still waiting for the 22-year-old to fulfill the promise he once showed.
A crisis of confidence coupled with a variety of injury problems has seen the former Southampton starlet stay in pretty much the same place he was when he arrived as an exciting teenager in 2011.
Although still with plenty of time on his hands, the England international is only one-year younger than Paul Pogba and was arguably ahead of the £100m midfielder when he left for Juventus in 2012. Since then, their paths could not have been more different.
Having recovered from the knee injury that kept him out of Euro 2016, Oxlade-Chamberlain has had a very good pre-season to date, scoring good goals against Lens and Chivas de Guadalajara, prompting the natural question to Wenger: can he finally fulfill his potential?
And the Arsenal manager was ready to put his neck on the line for the self-proclaimed 'Ox', claiming he has all the ability he needs to become a world-class performer but needs to start believing in himself to do it.
He's got it all
Wenger told Arsenal.com: "It’s a very important season for him. He has been out for a long, long time. He has been injured and did not go to the European Championships like he should have done if he had been fit.
"That’s why I’m cautious with him. I gave him 45 minutes [against MLS All-Stars], now 70 minutes. I hope I can get him through and fit for the start of the season.
"[He gives us] power, penetration. He has it all, Alex Oxlade-Chamberlain. It’s difficult what he doesn’t have - that’s why I would like him to get to the level he can go to.
"Maybe he doesn’t completely believe himself how good he can be and that’s the final step for him."
Oxlade-Chamberlin has regularly inspired Twitter tirades from Arsenal's online army but his goals against Lens and Chivas de Guadalajara had those critics rubbing their eyes.
We have attached both of the goals below just in case you somehow missed them. The first was the kind of goal Lionel Messi would be proud of while the second had a touch of Cristiano Ronaldo about it.