Paul Merson has questioned Arsene Wenger's reasons for allowing Jack Wilshere to join Bournemouth on loan.
Eddie Howe completed the signing of the Arsenal and England midfielder on Deadline Day, with Wilshere now set to spend the duration of the 2016/17 season at the Vitality Stadium.
Having been plagued by injuries in recent seasons, the guarantee of regular first-team football is understood to have played a key role in the Gunners' decision to allow Wilshere to leave.
However, speaking on Sky Sports News HQ, Merson believes the 24-year-old still has plenty to offer Arsenal, leading him to question whether Wilshere may have drifted out of Wenger's plans at the Emirates Stadium.
"I was very surprised to see someone of Wilshere's calibre to go on a season-long loan," he said. "I was surprised Arsenal would let him go for that long.
"He's different to what Arsenal currently have, he makes things happen, he can thread the ball through the eye of a needle.
"This is not a case of Wilshere needing to play football, there are a lot of other players at Arsenal who need to play football.
"Alex Oxlade-Chamberlain needs to play, Theo Walcott has barely kicked a ball and they haven't been on loan anywhere.
"You'd have to ask whether Wenger fancies Wilshere, that would be my question to him.
"Does he fancy him as a player and does he trust him as a player? Because there are other players at Arsenal who haven't performed and they haven't been out on loan."
With just two years remaining on his contract at Arsenal, Wilshere will be keen to work his way back into Wenger's thinking by making an impression on the south coast.
But Merson claims a string of positive performances could reflect badly on Arsenal's decision to sanction the loan, while he fears Wilshere may lose his love for the north London club in the process.
"If he starts ripping things up like we know he can at Bournemouth, and Arsenal lose two or three games on the trot, there are going to be some serious questions asked," Merson added.
"I'm not sure whether he has a long-term future at Arsenal, but that's from both sides because the lad could lose his love for the club.
"After all, Wilshere started at the Euros for England not so long ago so to come back from that to a year loan could hurt the player."