Saints are being linked with several left backs as Ryan Bertrand approaches the final month of the season with a new contract still not signed, the question is whether this might now be Saints preferred course of action.
Ryan Bertrand has been one of Saints best signings since we returned to the Premier League, by the end of this season he will have completed 7 seasons at St Mary's and is on course to have played around 230 games for the club in all competitions.
For a reported fee of £10 million Saints have truly got value for money from a player who has been at times outstanding and at worst steady in the Saints side and was a rock in a team that finished in the top 6 under Ronald Koeman and reached the League Cup final under Claude Puel.
There are those who will say that he is perhaps Saints best ever left back and there is a lot of evidence to back that up.
Certainly there were those who were more loved by the fans such as Mark Dennis, there were those that went on to achieve more in the game such as Wayne Bridge and there was of course David Peach a stalwart in the Saints side under Lawrie McMenemy and an FA Cup winner in 1976, not to mention Francis Benali who saw off many a rival to replace him in the team.
But despite a list of left backs in the last 50 years that reads like a whose who of the top echelons of English football, some at the start of their career such as Gareth Bale and others at the end of it like Graeme Le Saux, there is a case for Bertrand to be crowned the best ever.
None of his competitors for the title played as many top flight games for the club aside from Francis Benali and in overall terms with everything taken into account it is hard to make a claim that Bertrand has not been the best to play in that position in the club's history.
He has not been as spectacular as some, but he has played to a high standard season in season out for 7 full years and that is a record that cannot be matched.
But as they say all things must come to an end and Saints are at that crossroads where with the player turning 32 in the summer, they have to consider whether he has another year left in him, or is it time to replace him.
This is a tricky question that crops up from time to time at any football club.
Bertrand himself is seemingly not short of suitors, Leicester City are rumoured to be lurking to take him on a free transfer at the end of the season and there are others who have been linked including Arsenal.
Bertrand himself has expressed a desire to stay at St Mary's, he unlike many who harbour coaching ambitions when their playing career ends, sees his future as in the boardroom, perhaps initially as an assistant director of football type role, but moving forward perhaps even as a CEO.
Talks are said to have taken place between club and player about staying at the club and what role he will take in the future, but as of yet it seems there is no agreement having been made.
That has led to various left backs being linked with the club, up until recently it was assumed that Jake Vokins might be groomed to take over, but he does not seem quite ready yet, so if Bertrand does leave then an experienced replacement has to be found.
One name being iinked is that of Brentford's left back Rico Henry, who ironically is currently out injured with a hamstring tear.
Henry is no spring chicken though, he will turn 24 in the summer and has not played above Championship level, so the question is whether he can make the step up, the fee being quoted is £15 million, but I would be surprised if Saints would want to do business at that level given his lack of top flight experience
So the question is are the transfer rumours linking the likes of Henry just agents talk or indeed even Saints trying to put a little pressure on Bertrand himself to sign a new deal.
As I have mentioned I think that Bertrand can be considered one of our best ever signings, not just of the last decade, but of my lifetime given the size of his fee and the service he has given to the club, I have even suggested he could well be our best ever left back, but I do think he is not quite the player he was, he is still doing a job, but I just think his reactions have slowed a little, both defensively and in going forward.
This is understandable given his age and the big question Saints have to ask is whether he has another year left in him at the highest level, perhaps he might have two, but at some time in the near future we have to have a replacement lined up and is now the time to do it.
Ryan Bertrand will also realise that his time as a player is coming to an end, it seems he would like to stay with Saints but they cannot offer him the role he craves going forward, if that is the case is it in his own best interests to have one last move, from that perspective Leicester and Arsenal could potentially offer him more in the twilight of his playing career than Saints.
I do not expect this to be resolved until the end of the season, both Saints and Bertrand himself will be mulling over their options, if Bertrand does leave then it will be a sad day, he has been a great player for Southampton FC and deserves to be recognised as such.