Having signed professional forms back in 1986, Matt Le Tissier went on to spend his entire professional career with Southampton.
Also the first midfielder to score 100 Premier League goals, the 44-year-old made eight appearances for England at senior international level.
Now part of Soccer Saturday and a patron of Samsung's 'Win A Pro Contract' competition, we caught up with Le Tissier to discuss his former club's targets for the next season, as well as the futures of both Luke Shaw and Gareth Bale.
Having finished 14th last season, would it be fair to say that this summer is bigger for Southampton than 12 months ago? Is there a bit of pressure to build upon their performances from last year?
"I think that's a fair point. Both the chairman and the manager have spoken about European qualification and that sort of stuff. If you look at the squad that we had at the end of last season, you'd probably say that it wasn't good enough for that so if they are talking about that, you'd like to think that they are going to invest. I'd suggest that they need three or four decent signings.
"I think they are a bit short at centre-back and maybe in the wide positions. They probably need one more top-class centre-forward. Jay Rodriguez did very well with Rickie Lambert, but if you are going to start challenging for Europe, you are going to need three or four good forwards."
A Southampton player that has been linked with a move away, particularly to Chelsea, is Luke Shaw. How important is it that he continues his development where he is? After all, if he went to Chelsea he would be challenging Ashley Cole and Ryan Bertrand for a place so some times he may not even get in the squad.
"It's very important. Him, his agent, his family and whoever he has got around him need to take all those things into consideration. For me, I just want him to play football. In that situation I wouldn't have thought twice about staying somewhere that I will be first choice - guaranteed - as long as my form is good. You can't beat getting games under your belt at that age. He's got loads of time ahead of him to make a big move to a Champions League club if that is what he so desires. I know he was a Chelsea fan as a boy so that might have some effect later on his career."
Does he have what it takes to play for a club in the Champions League? And what about England at a senior level?
"From what I've seen so far I don't see any reason why not. I've not see too many deficiencies in his game that show that he is going to get exposed in any way. I've only seen a lot of very, very good things and there is no reason why he can't play regular Champions League football and become a regular for England. Ashley Cole is coming to an end and Leighton Baines still has a few years left in him - he's a very good left-back - so he will have some competition with him. But Shaw has got a very bright future ahead of him."
What, in your opinion, would represent a good season for Southampton next term?
"I think anything above where we finished this season really. If you can keep progressing, keep everyone fit and add to the squad, I would suggest that maybe a top-10 finish is not beyond the realms of possibility. We need to build a nice steady base and build gradually. There seems to be a decent amount of money there for transfers, so they should be able to build. It's not a Manchester City scenario where they can spend £20m every time you go to the market - it's not that kind of wealth, but there is enough to build."
Someone that you would have seen develop at Southampton is Gareth Bale. Now at Tottenham Hotspur, he's been heavily linked with the likes of Real Madrid. What do you think he should do? And what do you think that he will do?
"I think he should stay at Spurs to be honest. The Premier League would miss him for a start, so from our point of view watching him week in week out, I'd like him to stay. All the noises I am hearing, I think he will stay. He's only 23 and again he has plenty of time ahead of him. Spurs are that close to getting Champions League football and he could make himself so huge with the fans if he would stay there and kick them on into the Champions League."
They were very close to getting into the Champions League last season. How much did not signing a striker in January hamper their chances?
"A lot. They had Jermain Defoe and he missed a chunk of the season with injury, leaving them with Emmanuel Adebayor and he didn't always pull his weight. As I said, you need three or four strikers, not one and a half or two! That is what cost them their Champions League place without any question."
What did you make of England's displays during the two recent friendly matches?
"International friendlies at the best of times are difficult to judge, but at the end of the season the lads are ready to go on holiday. I don't think you should be judging the squad on those performances. If they were competitive games and you had those performances you'd be a little bit worried, but it wasn't and we've got those coming up. They are the important ones. What happened in the two matches against Ireland and Brazil wasn't overly important."
Did you manage to catch any of the Under-21s against Italy? They didn't perform well, did they?
"I thought we were second best unfortunately. We've got this fantastic defensive record at Under-21 level, but going forward we didn't look to threatening. I thought Italy were the better side and deserved to win."
They did have a few injuries and suspensions, but should we be concerned by the quality of the players coming through in the English game?
"There was quite a big difference in how many of our lads were playing regular football in the top flight compared to the Italians. I think that Nathaniel Clyne was the only player to have played a whole season. That is a big difference and a lot of experience. The Italian boys had been playing in some of the big leagues in Europe and that gives you an advantage - it showed last night."
You're a firm supporter of Samsung's 'Win A Pro Contract' competition. What is about the project that convinced you to get involved?
"You've got lads who have not been lucky enough to have been spotted, because sometimes you need some luck. You've got to be in the right place at the right time. This competition gives everyone a chance to put themselves in the shop window. Some players just develop a bit later than others.
"For these boys to get contracts at these clubs in League One is a fantastic opportunity. Hopefully they can go on. It would be great if I'm sitting on Soccer Saturday next season and one of their names comes up on the vidiprinter. They've got to do things right on and off the pitch and if they do, they could go on to have a 15-year career - it would be the best thing in the world for them."
You mentioned luck there. Is that something you needed to get your chance?
"Very much so. I was spotted playing for Guernsey Under-15s during a tour of Hampshire. I played three games and at one of those there was a scout from Southampton there. I actually played out of position on the right wing. Growing up I'd played in the centre of midfield but the teacher wanted to have a look at someone else in there and asked me to move out wide. I'd never really played there before, but I had a good game.
"The Southampton scout asked me to go and trial and they played me as right winger, because that is what they thought I was. That went well though and it was my lucky break. I didn't want to say that I was a central midfielder, I would have played anywhere so for the first two or three years at Southampton I played on the wing. It wasn't until I got a bit more confident that I said that I could play inside."
Finally, you've been in training for the Southampton half-marathon next weekend. How you feeling ahead of that?
"I'm feeling good. I did an 11-mile run yesterday. I've lost about two and a half stone since the New Year when I started doing it, which is good from a health point of view. I think I weigh less now than when I retired!"
Matt Le Tissier was speaking at the Samsung Experience Store, Westfield, Stratford, at the launch of Samsung Win A Pro Contract, a nationwide competition where amateur footballers can win one-year professional contracts at Swindon Town, Leyton Orient and Wycombe Wanderers. Register for a trial at facebook.com/samsungfootball.