A club will always find themselves in an impossible position if a player is in the final six months of their deal and there’s interest in a transfer.
They know that they won’t be in a position to demand a giant transfer fee, but the player could also start to play within themselves as they look to avoid an injury which would ruin a potential transfer in the summer.
Southampton find themselves in that situation with Ryan Bertrand just now, and it looks like Arsenal are showing an interest in signing him this month:
Arsenal considering a move for Ryan Bertrand with his contract up in the summer.
Talks continue with Saints but no deal done yet.
— Jack Rosser (@JackRosser_) January 22, 2021
The report indicates that he would come in as a depth option to backup Kieran Tierney after the departure of Sead Kolasinac, so it could be a big decision for the defender to make.
He’s already been through a situation at Chelsea where he was a bit-part player and he finally became a regular starter when he left to join Southampton, while Tierney is immensely popular at Arsenal so it’s hard to see him being dropped.
It’s very possible that Bertrand feels he’s advanced to a level where he deserves a chance with another elite club and he wants to prove himself at The Emirates, but it would be a risky option.
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It’s also believed that he’s open to staying with Southampton if they make a suitable contract offer – you would imagine that means a big pay rise and a few years on the extension – something that might be risky for a 31 year old defender when pace is a big part of his game.
He would certainly be a handy signing for The Gunners if they can pull it off, so it will be interesting to see what Bertrand decides to do if they agree a fee with the Saints.