O’Leary has seen hundreds of players come and go, whether as team-mates or members of squads he has coached.
There has always been a desire, he says, to ensure those who have arrived understand what the place is about.
“Even as a player, I hated it if someone who came in had something negative to say about the club, the city, the people, anything,” O’Leary explains.
“I take it really personally. So I do all I can to make sure people who come here have the best possible experience at Swansea City, like I’ve had, and that they see it how I see it.”
O’Leary first watched Swansea play against Manchester United in 1986, a friendly game which was played to raise money for the cash-strapped Welsh side.
It was his first experience – but certainly not the last – of a crisis at the club.
By his early teens O’Leary was involved in the Swans’ youth set-up, and by 1995-96 he was knocking on the door of the first team.
That was a season in which Swansea had no fewer than four managers – including the unknown Kevin Cullis, who lasted a week – and suffered relegation to what is now League Two.
Jan Molby was in charge for the back-end of the campaign, and it was the former Liverpool star who gave O’Leary his debut, in a 5-1 defeat at Bradford City in March 1996.
While all Swansea’s senior pros were in tracksuits, O’Leary and another youth prospect, Damien Lacey, travelled to the game in “trousers and a polo shirt” because in those days, there was no kit dished out to youngsters.