Like Scott Bain at Celtic, his tale is a heartening one. It underlines that playing part-time football in your early twenties does not necessarily mean you have missed the boat. Nor does seeing a lucrative transfer to England go sour.
Stewart, as recently as five years ago, had just finished a season combining playing for Cowdenbeath while working at Grangemouth refinery. Bain, meanwhile, was a brick layer while at Alloa Athletic after being released by Aberdeen. Given another chance at full-time football by Dundee, Bain has just finished a season where he won the treble with Celtic and also made his competitive debut for Scotland.
Stewart arrived at Dundee at the same time as Bain. He had finally become a full-time footballer having feared his hopes had been extinguished when being released as a youth player by both Rangers and Hearts. He got his love back for the game playing for Syngenta Juveniles in Grangemouth and started turning heads again after joining the senior ranks with Cowdenbeath.
Dundee manager Paul Hartley signed Stewart on a pre-contract in April 2014. The Dens Park side earned promotion to the top flight the following month and Stewart handled the step up in with ease. One goal, scored against Ross County in his second season at Dens Park, saw him bamboozle three defenders before stroking into the far corner of the net with his favoured left foot. Footage shows team-mate Nick Ross standing looking at him in awe with his hands on his head.
Stewart signed for Birmingham City in the summer of 2016 after two successful seasons with Dundee, where he was twice named on the short-list for the PFA Scotland Player of the Year Award. He had already started a third season with Dundee and so did not join his new team-mates at St Andrew’s until August. Crucially, it meant he missed the start of pre-season training and he took a while to get up and running in what was another jump up in quality.
When he finally broke into the side he encountered chaos in the form of manager upheaval. In his first season at the club he had to try to impress three different managers. Gary Rowett, who signed him, was sacked in December to be replaced by Gianfranco Zola, who in turn was replaced in April by Harry Redknapp.
“It didn’t go as I planned at Birmingham and I didn’t play as much as thought I would have. Three managers in one season didn’t help either,” he said after joining Aberdeen on loan the following summer.
“There were a lot of changes – a change of formation, didn’t play wingers. When Gianfranco Zola came in he didn’t play wingers and I struggled to get in squads.”
Stewart will hope another world star of the game in Steven Gerrard can see him perform to his potential on a regular basis and while the pressure is very much on him. Remarkably, while his CV confirms he stayed at Birmingham City for three years, and it’s where he joins Rangers on a two-year deal from, he played only 22 times for the English club and did not score.
Most of the time was spent back in Scotland, most productively at Kilmarnock in the first half of last season. He flourished under Steve Clarke and was given a roving role alongside Eamonn Brophy. He scored eight goals in just 16 appearances at Rugby Park, including a wonderful solo effort on his debut at Pittodrie of all places. Birmingham recalled him in January before sending him on loan again – to Aberdeen, where he has spent the 2017-18 season.
He never quite reached the heights there again but still provided glimpses of the exciting player he can be. Brophy made his Scotland debut last weekend against Cyprus and there’s no doubt Clarke, the new national manager, will be watching Stewart carefully.
It will be a new experience for Stewart, who will be over 40,000 fans to impress every second weekend. They will take a dim view if he disappears from games, as happened on occasion last season with Aberdeen. But when he is on form and running at defenders with the ball at his feet, there are few more thrilling sights in Scottish football.