adminFormer Scotland international Alan Hutton has opened up about one of the biggest regrets of his football career, admitting that he should have remained at Rangers until the end of the 2006/07 season instead of joining Tottenham Hotspur in January 2007.
The former right-back moved to North London after a prolonged transfer saga that dominated much of the January transfer window. Although the opportunity to play in the Premier League was tempting, Hutton now believes that leaving Ibrox halfway through the campaign was a decision he would have handled differently.
Despite being largely satisfied with how his career developed, the ex-Rangers defender has singled out his mid-season departure as the one decision he wishes he could change.
Speaking to FootballPredictions.com, Hutton explained that he rarely looks back on his career with regrets. However, he admitted that leaving Rangers when he did remains an exception.
“I don’t tend to look back on my career and think ‘what if’ or if I’d done something different; I’m happy with the way it panned out. But it’s probably the one thing for me, leaving Rangers in January 2007. I should have stayed till the end of the season,” he said.
Hutton Reveals How Close He Came to Rejecting Tottenham
Hutton also revealed that his transfer to Tottenham was far from straightforward, with negotiations dragging on for almost the entire January window.
According to the former defender, the pressure surrounding the proposed move became so intense that he nearly abandoned the transfer altogether. At one point, arrangements had even been made for him to travel to England, but he refused to board the plane.
Recalling the dramatic negotiations, Hutton admitted that he was initially determined to remain at Rangers despite the growing pressure from both clubs.
“I mean, it went on for pretty much the whole of January. I was getting told I had a plane arriving to take me down. I didn’t turn up for it. I was saying no at one stage, like, ‘That’s it, absolutely not, I’m not going.’ But yeah, I wish I’d just waited until the summer,” he revealed.
His comments underline just how close Tottenham came to missing out on his signature during a transfer saga that appeared to have several twists before reaching its conclusion.
Rangers’ European Run Still Haunts Hutton
One of the biggest reasons Hutton regrets leaving when he did was Rangers’ remarkable European campaign later that season.
The Scottish giants went on to reach the 2008 UEFA Cup final, creating a memorable run that the former full-back would have loved to experience as part of the team. With hindsight, he believes staying at Ibrox for the remainder of the season would have allowed him to contribute to that European adventure before considering a move elsewhere.
For Hutton, the disappointment is not necessarily about joining Tottenham, but rather the timing of his departure. Waiting until the summer would have given him the chance to finish the campaign with Rangers and potentially become part of a historic achievement for the club.
Ultimately, discussions with Tottenham chairman Daniel Levy and the opportunity to test himself in the English Premier League proved decisive. Despite his initial resistance, Hutton eventually agreed to the move to North London.
Looking back, the former Scotland international believes patience would have been the better option. While he remains content with the overall direction of his career, his January 2007 exit from Rangers is a decision he still wishes he had postponed until the end of the season.
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