The 40-year-old was last night appointed as assistant coach at Hearts to work alongside Robbie Neilson next season, with the pair having worked together previously as members of the backroom team at Falkirk. The former striker will begin in his new role next month.
As he pulls into the Tynecastle car park on June 1 it will be the 12th time in his career that Crawford has sought a berth at a new club, a list that includes Raith Rovers, Millwall, Dundee United and, for a short time, Hibernian. Having returned from England in 1997, the former Scotland internationalist would spent three years as a player at Easter Road.
Crawford has, though, never been considered a real Hibs man - the final season of his contract was served on loan at Dunfermline Athletic, a club he is associated with more readily - and so it is unlikely that he will take too long to get comfortable in Gorgie. He has settled into coaching already too, his role as assistant to first Steven Pressley then Gary Holt at Falkirk following on from a stint as the player-manager at East Fife.
The former forward will continue to build his reputation as part of a young coaching team at Hearts, with both he and 33-year-old Neilson to work under the auspices of director of football Craig Levein as the Edinburgh club attempt to gain promotion from the SPFL Championship next season. Crawford has seemed a quiet, articulate coach and his approach to working with a vibrant and young Falkirk team stuck in the mind of Neilson as he considered who to call in as his assistant.
"He'll assist with developing the players and he's got a great track record of producing talented young players at Falkirk," said the Hearts head coach, who was appointed after Ann Budge took control of the club earlier this month. "He's an international striker who's had a great career in the game. In the last six or seven years he's been focusing more and more on the coaching side of things.
"I know that he'll be a big benefit to the club. He's got a great wealth of knowledge and the boys will learn from him, especially the attacking players. I'm certain that he'll be a big benefit to the football academy as all the coaches, myself included, look to work closely together with all age groups."
The arrival of a new coaching team following the tenure of Gary Locke last term has ad the effect of opening the windows at Tynecastle and airing the place out. Neilson has spoken candidly of his intention to add "six or seven" new players to his squad, while teenage striker Gary Oliver is also expected to sign a new one-year contract at Hearts after making his debut in the Premiership last term.
Neilson is faced with the demands of recruitment for the first time in his career but is unfazed about the challenge of trying to attract new faces to Tynecastle ahead of the new season. A rugged, eager full-back during his time on the pitch, he has retained an alluring enthusiasm since stepping into coaching.
"To say this job has come too early for me, time will tell, but Craig [Levein] will support me and the new owner Ann [Budge] has been fantastic," said the one-time Scotland defender. "I've been working towards this for most of my playing career, if I am honest.
"I was a player that didn't possess the best of technique so my game was always about looking at the opposition, trying to get myself into positions and trying to understand the game.
"I built that up and then coming into the coaching side of things is something I really enjoyed. It's a great opportunity and I want to continue the work I've been doing."
Neilson has been emboldened by the presence of Levein as director of football. "I've known Craig for a long time, working under him as a player, and the first thing I said was: 'You'll need to support me in this.'
"He will be there to speak to and lend his experience. I'm not under the impression that I will be the best coach in the world straight away. As soon as you get a management role it is a learning process."