The 26-year-old, who has committed to spending the peak years of his career at Easter Road, learned his trade in the game across the city at Gorgie, where he featured in a Hearts youth team with current Tynecastle goalkeeper Jamie MacDonald.
Craig's senior career has been something of a slow burner since then, with spells at Falkirk and St Johnstone, but he reckons that leaving Tynecastle as a teenager for Ipswich Town's high-flying youth team was the making of him. "I was at Hearts for three or four years before I went down to Ipswich," said Craig. "I enjoyed it, but when Ipswich came in, I looked at their facilities up against Hearts, who had nothing at the time, and I knew it would be the move that would make me better as a player.
"It was nowhere near the start of the Romanov era yet, but there were a few things that went on at the time I wasn't too happy about. Big Jamie was the goalie and it was a good squad we had there. We've lost touch but he's a guy I have a lot of respect for, and it's great to see him doing well. We'll probably speak after the game - or not, depending on how the game goes! But there were another 15 guys in that Hearts team who didn't make it so it shows you it's all well and good having ability but you have to be lucky as well. "
Craig's arrival at Hibs took seven years longer than it might have done. Having first encountered Tony Mowbray as a coach in East Anglia prior to the Englishman becoming manager at Easter Road, he approached his former mentor when it was time to return north of the border. Unfortunately, midfield positions were already filled, so it took two-and-a-half years at Falkirk, and five years at St Johnstone, to bring the Borders-born player back to the capital.
"When I left Ipswich he [Mowbray] was the manager of Hibs and the first guy I phoned to see if he could help me out," Craig said. "He was honest enough to say I wouldn't have played at Hibs because their midfield was strong at the time with the likes of Scott Brown and Kevin Thomson. It's great to be here now, though, and I want to be successful with it. I was at Hampden for the semi against Falkirk last season, and even last Saturday when you hear the fans belting out Sunshine on Leith, they're special days."
While the surroundings at Easter Road seem to suit him, Craig's big move to the capital this summer had to endure a difficult start. Criticism of manager Pat Fenlon and his new signings reached a crescendo after a 1-0 defeat in the league at Tynecastle, but the Irishman and his players appear to have ridden out the storm.
"It was difficult when people were saying we didn't care," said Craig. "It was hard to take because two months earlier me and big Jonesy [Owain Tudor Jones] were at clubs who finished third and fourth in the league and everyone was saying how great we were. Four games later all of a sudden we don't care. So that was difficult to take. Particularly when you have come to the club as an attacking player to try to improve and make them better and four games in you haven't scored a goal as a team.
"But we knew we had a good squad of players here and it was important that we stuck together and we are getting rewarded for that now."
Victory against their rivals would exact a measure of revenge for the 2012 Scottish Cup final defeat and set up an opportunity to write themselves into club folklore. "It can work both ways," said boss Fenlon. "It is a difficult time for them [Hearts] right now, but there is also less pressure on them. It is a home tie, a cup quarter-final against our biggest rivals, and a great incentive to get into the semi-finals."
Hibs last won this cup in 2007, and Craig unwittingly played a part in their victory. His Falkirk side removed Celtic from the competition at the quarter-final stage, only to lose meekly in the semi-final against Kilmarnock at Fir Park. Once again, the favourites have been removed early.
"I've been to a few semis but never a final and I want that to change," said Craig. "I've signed for a team and play with a squad capable of doing that."