O ne is preparing for the Barclays Premier League, one is back at Easter Road, and the other two are without a club.

If there is a sentiment that still connects Stephen Dobbie, Garry O’Connor, Derek Riordan and Tam McManus, it is one of regret, of the understanding that they did not realise all of their ambitions.

Only Dobbie can say that he has moved beyond it now, having belatedly found realisation and purpose while on loan at Dumbarton. He had left Hibernian by then, for a spell at St Johnstone that was also unfulfilling and led to his stint in the third division. Overweight and listless, he was surrounded by part-time players whose dedication acted like a rebuke. “It opened my eyes and made me want to get my career back on track,” Dobbie has since said.

Ian McCall saw the talent that the forward could still call upon and took him to Queen of the South, where a new attitude and determination enabled the striker to flourish and earn a move to Swansea City. Last season, he played a vital role in the Welsh club’s run to the Championship play-off final, where they defeated Reading 4-3, with Dobbie scoring one and setting up another.

To O’Connor, Riordan and McManus, the triumph of their former team-mate must have felt chastening. All four were involved when Hibernian lost the 2004 League Cup final to Livingston, the game when the great promise held within the graduates of the club’s youth development scheme was confronted with the harder realities of the game; they had beaten Celtic and Rangers on their way to the final, but then came up short.

O’Connor and Riordan started up front, while McManus and Dobbie came off the bench, and it was the former pairing who were considered the brightest talents. O’Connor was a broad, powerful, quick and direct striker, capable of a fierce shot and an adamant, almost heedless attitude; Riordan was a thin, delicate attacker, whose technical prowess was accompanied by arrogance and a scowl.

O’Connor ended up at Lokomotiv Moscow, where a lavish wage could not compensate for an empty lifestyle; Riordan moved to Celtic but could not adjust to the demands for industry and application under Gordon Strachan, or the need to discard a sullen sense of entitlement.

“They were a very good partnership,” says Donald Park, who was a youth coach at Easter Road as the two players developed. “Garry has achieved, but you hoped that he had done better down south. With Derek, he’s Hibs’ all-time top scorer in the Premier League. People say that he could work harder, and I’m sure Derek thinks that a bit, but technically he’s fantastic. I’ll never be negative on them; we can always think they can be better, but what they’ve achieved from when they were two young kids is great.”

Park’s regard for the two survives because he can look back far enough and remember them when they were teenagers, full of limitless hope and guilelessness. But that lack of insight never left them, so that both players failed to learn from their experiences in the way that Dobbie did. Riordan returned to Easter Road, but fell back into the unedifying routine of considering himself the heroic figure in the side, somebody operating beyond the fundamental obligations to run and work for the good of the team.

O’Connor talked often enough of a renewed attitude after moving to Birmingham City, occasionally stirring old recollections of the raw power of his younger days. But injuries thwarted him and he was released by Barnsley last season. Recently abandoning his Ferrari after a prang and being caught by police with a suspect white powder in another incident (although he has been released without charge pending further investigation), tells of a player still struggling to restrain his impulsiveness.

McManus was the most streetwise of the four, and could be an irrepressible, buoyant presence up front, with a clear eye for goal. But he, too, failed to heed the advice that a footballer’s life reaches beyond the training ground, so that bad habits came to undermine his ability. “I should have worked harder at Hibs,” he admitted recently. “I had a bad diet, that kind of thing, and I wasn’t fit enough. I’m a better player now.”

Perhaps all four of them are better now, but only Dobbie can look forward to the coming season without self-reproach. Riordan has an offer from Houston Dynamo, but would rather remain in the UK, while McManus may yet re-sign for Falkirk, where he spent the last campaign. The latter has also realised the need to be committed, to think beyond the extent of your own talent, and to work hard enough that your potential might be realised. At 30, there is time yet for McManus to revive the best of his career.

The same opportunities lie in front of O’Connor (who has been working with his own fitness trainer during the close season) and Riordan, even if they both seem unable to discard some old bad habits. Dobbie should be an example to them both of what can still be achieved.

“Attitude is the most important ingredient for anybody to become a great player,” says Park. “Dobbie’s obviously realised what is required to reach [the Premier League]. Hopefully they will do the same.”