Looking ahead has become uncomfortable for two players whose potential once burned twice as bright, but which appears to have fizzled out before either has reached their 30th birthday. It is testament to how prodigious they once were that their names still stand out amid the numerous displaced players that are willing to listen to offers this month. It is indicative of how far they have fallen in recent years that few will be surprised at their presence on such a list.
Both are now in limbo after unproductive spells at their last clubs – Riordan left Bristol Rovers last month, with O'Connor departing Russian side Tom Tomsk soon afterwards – and it seems likely that they will have to bend over backwards to get contracts elsewhere. It is a reality which causes you to squint in light of the potential they had shown during their formative years at Hibernian; their time at Easter Road played out amid a clamour to predict at what level they might end up. That question has still to be answered, of course, except the context has now changed.
There is some comfort in covering their careers in a veil of nostalgia so as to disguise an uncertain future, although it would be unfair to write them off completely. At 29, both strikers have enough time to recover both their reputations and an appetite for goals – Riordan has yet to score in a competitive match since returning from a short spell with Chinese club Shaanxi Chan-Ba 14 months ago – but it is up to them to show they have the stomach for it.
It is that which will inform their next move. O'Connor made a lucrative switch from Hibernian to Lokomotiv Moscow in 2006 and Riordan followed him through the exit a few months later on his way to Celtic, transfers which might have defined their careers. It remains to be seen whether they consider themselves to have been fulfilled since then.
"When kids have big success early in their careers and make a lot of money, sometimes their heads get swayed and sometimes they forget why they became football players in the first place," said Craig Brewster, who spent a season playing alongside both O'Connor and Riordan at Easter Road after signing in 2001. "That hunger, that enthusiasm, that strength to do well, that attitude that they had when they first burst on to the scene, maybe that has lost its way.
"That is why people are not taking players – not just Riordan or O'Connor, but many players. Sometimes when people make money, they get comfortable and they don't want to then push for the next level. They are happy to sit on what they have got instead of still aiming for, and trying to achieve, bigger and better things."
The words are delivered firmly but the Crawley Town first-team coach still treats a discussion about the pair with a parental instinct. It is understandable given that he joined Hibs as an established pro, accepting a remit not just to score goals but also to help sculpt his younger team-mates. He would come to play alongside O'Connor in attack, the pair sharing 14 goals between them.
"What I saw in him back then was that he had enthusiasm, he wanted to run, he was hungry and he was a strong boy," said Brewster. "When you have got the combination then you have got a chance of being a success. Things have fallen away, although financially he is okay, but sometimes you forget why you are there in the first place, what got you there – a love of playing football."
That was enough to fuel Brewster in a playing career that lasted into his 40s. Any contrast is mitigated given the former Dundee United striker was made to wait before starting his professional career – "I didn't go full-time until I was 26. Those two were full-time when they were around 17," he said. But there is a sense that both O'Connor and Riordan have perhaps suffered for being given too much, too young.
"Sometimes players don't realise what it is like to come from that and all they know is that they get paid well for a few hours training a day," said Brewster. "You need that enthusiasm to continue throughout your career; you have to be a certain character to say 'okay I'm financially well off but, here, so what?' Once you are successful, how much do you want to continue that success? That would be the question that I would ask O'Connor and Riordan: 'do you have the same hunger?' I would love them to think back to what got them there in the first place."
Brewster had returned to the point where he started. Perhaps it is time for two old team-mates to do the same.