George O’Callaghan regards not signing for Tottenham as the "massive massive mistake" of his football career.
Speaking with former Cork City teammate Graham Cummins on thepodcast, O’Callaghan talks about his breakthrough years at Port Vale where he was regarded among the hottest prospects in English football.
“When I started at Port Vale I got in the first team and I remember Arsenal came in for me when I was 18.
“I was waiting outside the manager John Rudge’s office, and Pat Rice, who was Arsene Wenger’s assistant at the time, came out and said, ‘George, we can't get you this time, we’ll get you next time’.
“I went into John Rudge and said ‘I want to go to Arsenal’. And he said ‘well they’ve only offered one million, we want two million for you’. And he goes ‘you’re not going to get a game before Petit and Vieira, so stay here with me’.
“Coming from Whitechurch, brought up in the GAA community, you kind of think, will I stick to what I know. So I stuck with Port Vale, who were really good at the time in the Championship. There was a really good side and a really good family feel to it.
“But then John Rudge got sacked and Brian Horton came in and from playing against Liverpool in the FA Cup the week before, Brian Horton said, ‘forget the rest of the season, you're with the youth team for the rest of the season’, and he brought in a load of new midfielders.
“And believe it or not, in those days I was quiet and didn’t really stand up for myself.”
It took O’Callaghan over a year to get back in the Port Vale first team under Horton but he soon impressed enough to draw interest from Spurs.
“After about 10 or 11 games, David Pleat tried to sign me for Tottenham.
“But Brian Horton said, you’re doing really well, and offered me a two-year deal and doubled my money.
“I rang John Rudge and asked him what I should do and he said, ‘play another couple of years at Port Vale and then go, because you won't’ play at Tottenham’.
“So I took his advice and signed the contract. Within about 14 months I was finished, sent home.
“I just didn't have the advice. I was happy living in Stoke, I was there since I was 15, it was my home. In the north of England they say London is too big, stay away from it, so I was brainwashed that way. But it was a massive mistake, a big big mistake.
“I was too comfortable in the situation I was in. I probably didn’t have the guts to go ahead with it.
“I loved playing for Port Vale but I should have pushed for Arsenal and Tottenham.
”And then you can always go out on loan if it doesn't work out."
During his spell at Port Vale, O’Callaghan became good friends with the club’s most famous fan, Robbie Williams.
“Just after he left Take That, Robbie went to all the games.
“The first time I met him was at a testimonial. We were in the gym and Robbie came in with Jonathan Wilkes. And they were like, ‘which one’s O’Callaghan’.
“And I was like, what’s Robbie Williams want with me now.
“And he said ‘I sold you on Player Manager to Leeds for 15 million last night.’ So I actually think Robbie thought I was worth 15 million and was better than everyone else.
“We just had a friendship from there. We used meet up and he was around the club all the time.
“He was always very good to me. I went out with him one night and I was going home and I needed his autograph for my sister. And he took off his boxer shorts and gave them to me for my sister. She has them framed at home.
“Robbie was one of us then but he went away to America for a couple of years and came back a completely different guy.
“But I think he’s playing in Port Vale over the summer so I’ll expect free tickets for that one.”