On January 30, 2008 the then 23-year-old Scotland right-back was sold to Tottenham Hotspur for £9 million, eclipsing the previous highest fee the Ibrox club had received for a player when Giovanni van Bronckhorst joined Arsenal for £8.5 million in the summer of 2001.
Thirteen years on from Hutton’s protracted move to Spurs, it is a landmark figure which should be surpassed before too much longer, given the market value of Rangers’ current first team squad built up by Steven Gerrard.
While Rangers look ahead to operating a player trading model which will rebalance finances presently underpinned by the ongoing support of investors such as chairman Douglas Park and vice-chairman John Bennett, back in 2008 the sale of Hutton came amid a gathering storm of uncertainty off the pitch for Sir David Murray’s ownership of the club.
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The global banking crisis unfolding at the time saw Rangers’ debt moved from the ailing Bank of Scotland to Lloyds Banking Group as a chain of events unfolded which ultimately led to Craig Whyte’s ill-fated takeover of the club in 2011 and its descent into administration the following year.
But boardroom politics had been of no concern to Hutton, who made his way through the Rangers academy set-up to make the breakthrough at the club he supported as a boy.
In the summer of 2007, he had signed a new five-year contract and envisaged seeing it out as he targeted silverware under the management of Walter Smith, who had returned for his second spell in charge earlier that year.
Hutton’s form as an attacking right-back also saw him called up by Scotland for whom he impressed in the valiant but unsuccessful Euro 2008 qualifying campaign, catching the eye of several English Premier League clubs.
Spurs, Manchester United and Newcastle were the three most consistently linked with him at the time and it was the London outfit who made their move when the transfer window opened in January 2008.
Rangers, who had been put up for sale by Murray two years earlier, accepted Spurs’ bid when it was lodged on January 4 – but Hutton was quick to turn down the move.
“The player has said he’s going to stay and that’s it,” said Smith at the time. “From a footballing perspective that is good news.
He has been doing so well for us that we didn’t want to lose him. We still have someone who has been one of our best players.
“It’s pleasantly surprising in many ways. There are two things in football – the financial situation Scottish clubs find themselves in, and the footballing side.”
But Spurs were not discouraged and four days later offered Hutton improved personal terms.
Again, he declined. Again, they refused to take ‘No’ for an answer, doubtless encouraged by Rangers’ willingness at boardroom level to push the deal through.
“I turned down Tottenham multiple times, I didn’t want to go, I told the manager I didn’t want to go and I didn’t,” reflected Hutton on Football Insider last year. “At the end of the day, if Rangers agree on a fee, they’ve agreed on a fee and they’re willing to let you go so it’s kind of out of your hands a little bit.
“I remember it like it was yesterday. I turned them down multiple times, I was Rangers through and through and I never wanted to leave but when Rangers come and say: ‘Look, we’ve accepted this bid,’ it is what it is.”
In only his third appearance for Tottenham, Hutton was part of the side which beat Chelsea 2-1 after extra time in the League Cup Final at Wembley.
He also went on to play in the Champions League for Spurs, was capped 50 times for Scotland and had eight tumultuous but ultimately fulfilling years with Aston Villa before announcing his retirement as a player in February 2020.
But there would have been times when Hutton may have reflected on what might have been had he stayed longer at Rangers, the club reaching the UEFA Cup Final in the season he was sold and then winning three successive domestic titles under Smith.
Hutton provided an insight into his feelings during an interview with Aston Villa’s official YouTube channel in 2017, making his enduring affection for Rangers clear and still expressing an element of regret at the manner in which he became the subject of that record transfer.
“It was something special (to play for Rangers),” he said. “To grow up and watch Rangers, especially in the good old days if you like, to be part of that and play in some big games for them was really what dreams are made of.
“It was a great thing for me and I’m really happy to have started my career off there.
“To be honest, I just wasn’t ready to leave yet. I was still young, I was happy where I was.
“I was playing well, I was enjoying every minute of it really.
“It was my boyhood club, so I really found it difficult to leave. I wasn’t really finished with everything I wanted to do there.
“At that time of my career, I just wanted to keep playing. It didn’t quite feel right. But, eventually, it did happen.”