Across the Atlantic, the country where he would grow up was heading in the other direction, about to qualify for the third of six consecutive World Cup finals. For a young footballer with big ambitions, it was the right move at the time.
At least, that's the way it looks 14 years later. As another qualifying campaign draws to a close, with Scotland not even fit for this weekend's play-offs, those who have already booked their place in next summer's finals include a US team with a lad by the name of Holden in their ranks. He is 24 now, with a Texan drawl and American citizenship, but it's the same Holden all right, born in Scotland, to a Scottish mother, with a Scottish accent to turn to when the mood takes him.
Assuming he is still in the squad next summer, Holden will probably be Scotland's only player in South Africa. "If I make it to the finals, I'll be saying to the people who are pulling for the US and pulling for me that I have Scottish ties. I was born there after all. I would, in a sense, be representing two nations. I could fly an American flag on my back, and still have that loyalty towards Scotland. One of the things I would love to do some day is play against Scotland for the United States."
Holden has emerged as one of the best attacking midfielders in the MLS. His Houston Dynamo team, coached by two Scots, Dominic Kinnear and John Spencer, just missed out on a place in next Sunday's MLS Cup final after they lost 2-0 to LA Galaxy on Friday night. His contribution to their season has impressed the US coach, Bob Bradley, who has rewarded him with ten caps and the prospect of an experience next summer that his Scottish compatriots can only fantasise about.
"I would love to see Scotland doing well, but my focus now is on the US, and hopefully doing well in South Africa," says Holden. "It has always been my ambition to play in the World Cup so, if the opportunity came, it would be a dream come true. I've been in and around the squad for the last six or seven games, but I still have a ways to go. There are six or seven months yet, and I'll have to keep playing good football to be selected."
This, after all, is a team ranked 11th in FIFA's world rankings, 35 places ahead of Scotland. In the summer, they reached the Confederations Cup final, where they were beaten by Brazil. He would have been included for this week's double header in Europe, against Slovakia and Denmark, had it not been for MLS play-off commitments. On Friday night, he was up against David Beckham, which isn't much of a step down. "It's always hard to compare, but I think our team (Houston] would be lower end of England's Premier League, upper end of the Championship.
"There are some really talented players here, players who have done well in leagues overseas. There is a lot of hype around soccer at the moment with the World Cup coming, and the US doing well at the Confederations Cup. These are good times for soccer in this country."
It's certainly a long way from Cults, the village where he spent his earliest years. Then, he played for Aberdeen's youth teams under Chic McClelland. Eoin Jess, an Aberdeen striker at the time, attended one of his birthday parties.
In 1995, the oil industry took his English-born father, Brian, to Houston, where the family grew up. After graduating from Clemson University, Stuart had a brief spell with Sunderland, but never played for the English club thanks to a serious eye injury sustained when he was attacked outside a Newcastle bar. On returning to America, he signed for Houston, and in his first season, scored in the penalty shoot-out that won them the 2006 MLS Cup.
Before long, he was wanted by the national team, which prompted his decision to become a US citizen. "I wanted to play for them in the Olympics," he admits. "Our whole family became citizens so it wasn't like it was just me. We are proud to have lived in the States for 14 years. We're also proud of our Scottish heritage, but when it came down to a footballing choice between the US and Scotland, I felt loyalty to the US. They were the first ones to contact me and show an interest. For me, it was a no-brainer."
Holden has never looked back. Not only did he score in the Beijing Olympics, his full debut in this year's Gold Cup was followed by a 25-yard, last-minute equaliser against Haiti. The squad for that tournament was experimental, but he kept his place for what remained of the World Cup qualifying campaign.
An energetic, mobile midfielder with a sweet right foot, his task now is to establish himself in Bradley's first-choice XI. If, as some are predicting, Fulham's Clint Dempsey is given a more advanced role in the finals, it may not be so outlandish a prospect. It has been a head-spinning, emotional time for Holden, whose father lost a long battle with cancer in February.
"It was a bad start to the year, but as it's progressed, it has become better and better in footballing terms. I'm a full international now. I'm excited about that, and it's something I want to keep being a part of."
His team-mate, Brian Ching, says that Holden craves the spotlight, "in a good way". Affectionately known as "Peanut" on account of his allegedly small head, he has become something of a celebrity in Houston, with the spiky, highlighted hair of a boyband singer, and the playful bravado to go with it. A regular visitor to the local children's hospital, he won US Soccer's Humanitarian Award in 2008.
Holden knows how lucky he is. He loves the lifestyle, the climate and the culture he was exposed to in Sugar Land, the affluent suburb of Houston where he grew up. His brother, Euan, also plays football. His younger sister, Rachel, is an athlete. Had they remained in Scotland, they would not have enjoyed the weather, the facilities or the college system that has been to their benefit in the States.
But, if America is responsible for Holden's growth, his homeland planted the seed. "Scotland has had a big part in it," he insists. "I grew up around football. It's what I liked doing every day. I played a lot with my mates in the park, trained with Aberdeen youths and watched football on TV every day. When I came here, I was lucky enough to get the right breaks, but I had the right passion for the game."
It has never left him. "Chameleon" is another of his nicknames, thanks to the broad Scottish brogue he can turn on like a tap. Spencer, Houston's assistant coach, is a reminder of the world he left behind, as are the relatives he visits every other winter in London, Manchester and Aberdeen. "I miss the British sense of humour, which is a part of me people here don't always understand. And I miss the football culture, watching it and being around it all the time. Soccer is a growing sport over here, a sport that will hopefully be mainstream one day, but at the moment it's not."
No wonder there is speculation that Holden will be back in Britain next year. His contract with Houston Dynamo is about to expire, which means that he will consider his options shortly. Like many of his team-mates in the American national side, his development depends on exposure to a higher level of football. England, if not Scotland, would provide that. "I love it here, the lifestyle and all the rest of it, but I'm definitely not ruling out a move back to the UK," he says.
More than a few clubs will be glad to hear it.