Hibs finished third in 2004/05 and fourth the following season under the stewardship of Tony Mowbray. Along with O’Connor, the team boasted the talents of fellow academy graduates Kevin Thomson, Scott Brown, Steven Whittaker and Derek Riordan, not to mention the likes of Gary Caldwell, David Murphy, Ivan Sproule and Guillaume Beuzelin.
Though the majority would remain for the 2006/07 campaign, as Hibs ended a 15-year spell without winning a major trophy by lifting the League Cup, O’Connor and Riordan had already departed. O’Connor signed for Lokomotiv Moscow a month before Hibs were defeated 4-0 by rivals Hearts in the semi-final of the Scottish Cup. Riordan, absent from that game due to suspension, left for Celtic that summer.
Asked by Simon Ferry for Open Goal why that Hibs team never challenged for a title despite routinely taking points off both Celtic and Rangers, O’Connor responded: “Because, basically, they weren’t wanting to pay us. They were in a transition period where they had splashed all that money on the previous players and they were trying to balance the books.
“I was on £750 and I was banging them in left, right and centre. The rest of the boys wouldn’t even be on that.
“You see if that team would have stayed together just one more season, I think we would have won the league. They were that good a group.
He also expressed regrets at leaving when he did, adding: “I left too early, I think, going to Russia. If I’d stayed we’d have had a good chance of beating Hearts [in 2006] and winning the Scottish Cup.”