The choice was Manchester or Liverpool. He had just met the man who epitomised Anfield and had gone back to his room at the Adelphi Hotel to consider a career-defining move. He opted for Manchester.
In a parallel life, Lou Macari would probably have won three European Cups and five league titles instead of the single FA Cup winners' medal he did collect with Manchester United. There was an extra £20 a week – 10 times that in today's money. Macari never regretted it; Bill Shankly snorted that he'd only wanted him for the reserves.
In a parallel life, Gareth Barry and Steven Gerrard would be lining up alongside each other for Liverpool for tonight's Carling Cup semi-final as they almost certainly will do for England in the summer.
The Kop, to quote a chant that will be directed at him tonight, might want to "stick Gareth Barry up your arse" but he would have been a formidable partner to Gerrard in the heart of Liverpool's midfield, which collapsed so comprehensively at Bolton on Saturday night.
The value of Lucas Leiva has never been better expressed than in his absence. Without anyone to hold the centre of the field together, Bolton, a team that had previously beaten only Macclesfield and Stoke at the Reebok Stadium, bypassed them completely.
There will be another chant at Anfield tonight that Barry is English football's "one greedy bastard". There are actually plenty to choose from but, unless you want to manage in the wastes of the Caucasus for an erratic warlord as Ruud Gullit did with Terek Grozny, money is seldom the overriding principle.
"People say to me that I have made the right decision in joining City," said Barry. "Liverpool is a fantastic club with a great following but I won the FA Cup last year and I've played in the Champions League.
"Liverpool were still interested when I decided to join Manchester City. I thought about it really hard but the things the clubs were talking about made my mind up. I felt City were on the up, whereas Liverpool were finding it a bit tougher."
If that were so, then Barry was to prove rather more astute than Macari when it came to peering into the future. In the summer of 2009, when his £12m transfer from Aston Villa was negotiated, Liverpool had just finished second, 36 points ahead of Manchester City, who had stumbled into 10th place. Since then, their fortunes have turned dramatically. Perhaps had he not been so convinced he would land Barry, Rafael Benitez might not have allowed his relationship with Xabi Alonso to freeze over, something that came all too easily to the Liverpool manager.
"It wasn't an easy decision," Barry reflected. "I was signing on promises being made really and in football promises are made all the time.
"But, sitting here now, I think it was the right call. I took a bit of stick for a few weeks, as you know, but I took the long-term view and believed that at the end of the contract I could say I made the right decision.
"I don't get as much stick now. Like everything else, it dies off slowly. Mind you, I have not been back to Villa Park this season. I remember watching a friendly when the transfer saga was going on and the Liverpool fans were singing: 'You can stick Gareth Barry up your arse.' That might have got into my head a little bit but it is part and parcel of football."
So, too, is the kind of excoriating language Gerrard listened to on Saturday night, delivered by Kenny Dalglish, a man he idolised, accusing his players of betraying Liverpool's history. Gerrard has a parallel life, the one that involves accepting Jose Mourinho's offer to join Chelsea seven years ago or his more quixotic approach to be part of his team at Real Madrid.
There might have been a few more pieces of silverware and a lot more money but the absolute love that Liverpool gave him would have been diluted.
No Liverpool player talked to the press in the wake of the 3-1 defeat at Bolton that Dalglish acknowledged was the worst since his return to Anfield. It was not a time for promising to "bounce back" against Manchester City. Now, however, Gerrard was able to add some perspective.
"You have to win every game, the people new to the club will understand that a bit more after a performance like that," he said. "You can't do it here [play poorly]. The fans won't accept it and they don't deserve it. It is not allowed, otherwise you will get shouted at and criticised by your manager as we all have been."
In a 1-0 first-leg win secured by his first-half penalty and some highly organised defending after the interval, Gerrard did some shouting of his own as Roberto Mancini attempted to conduct a post-match interview in the tunnel.
Gerrard was enraged that Mancini had waved an imaginary card, assumed to be red, when Glen Johnson attempted a tackle not dissimilar to the one that had seen Vincent Kompany dismissed against Manchester United a few days before.
"It got blown out of all proportion, it was more of a heated conversation," said Gerrard by way of explanation. "It wasn't a head-to-head duel or anything like that. I'd read his comments in the media where he was criticising Wayne Rooney for waving cards and he was waving a card at Glen Johnson. I just thought I'd tell him he was wrong."
Just as Barry's career has turned since he chose Manchester over Liverpool so Gerrard's has stalled. He is unquestionably the greatest footballer to have graced Liverpool since Dalglish himself, yet injury and loss of form meant his contribution to the last year of Benitez and the only year of Roy Hodgson was minimal. There was just one great display that saw a second-half hat-trick against Napoli, although the signs after his latest comeback have been wholly encouraging. It is, nevertheless, nearly six years since his last taste of silverware and he has yet to play for Liverpool at Wembley.
"It would mean nothing for me to lead them out there," he said. "But to lift the cup at Wembley would mean an awful lot. It would be a dream come true. If I lead the club out at Wembley and we lose, I will remember it in a bad way. To get to Wembley is the target; to win there is the dream."
Gerrard said that he did not lie awake at night wondering if Liverpool could ever compete with Manchester City and that he would "drive myself crazy" if he did. However, if it came to a choice between qualifying for the Champions League and winning a trophy, it would be no decision at all.
"I totally understand there is a balance for the club financially," he said. "I understand that the top four is massive and at the beginning of the season it is probably the main aim but, as a player, I don't want to be saying I finished in the top four a few times. I want to look back and say I won the Carling Cup three times. Or four. Or five."