Michael Johnson, of whom the same question has long been asked, effected the transition by winning the Olympic 200-400 metres double in his home country last summer - even if the events of 1997 have dimmed his star's lustre.
While the American's achievements in Atlanta were widely celebrated, those of the Canadian - an Olympic 100m title in a world record time of 9.84sec - remained relatively unsung.
But since he ran clear of the injured Johnson over 150 metres in Toronto on 1 June, earning himself $1.5 million (pounds 925,000) in the process, Bailey's fortunes have risen in inverse proportion to those of the double Olympic gold medallist.
Johnson has failed to regain form following the quadricep injury which halted him half-way through the self-styled One-To-One Challenge, and his poor showing in Paris on Wednesday night, when he lost his eight-year unbeaten record over 400m, caused him to make an early return home from Europe.
Bailey has since run 9.94sec in Nuremburg, and his winning time of 10.07sec in the rainswept Paris meeting indicates he is a clear favourite to win his latest 150m challenge at Sheffield tomorrow against a domestic field headed by Linford Christie.
The financial incentive of tomorrow's Securicor Challenge - a winner- takes-all figure of pounds 50,000 - is relatively slight for a man whose last 150m race was worth pounds 10,000 per metre.
But Britain's finest will be hard pushed to prevent the 29-year-old world and Olympic champion adding to his bank balance.
Bailey is predicting that he will better his world record this season - "I know I am very capable of running faster than I did last year" - and you would be foolish to bet against it.
Christie has won his two previous meetings with Bailey over Sunday's distance in Sheffield but Bailey predicted a different result this time: "I'm in better shape than before," he said. "I'm faster and stronger and lighter - I'm about 8lb down on this time last year."
There are marked similarities between Christie and Bailey - both were born in Jamaica and spent their early childhoods there before emigrating; both were relative latecomers to top level sprinting.
Christie did not win his first major title until he was 26; Bailey did not even break 11 seconds for 100m until he was 23. Having taken up the sport seriously in 1993, however, he has improved his time every year.
When Bailey decided to give up his lucrative career as a marketing and property consultant to concentrate on his running, he approached it as if it were another line of business, leaving his girlfriend, Michelle Mullin, and baby daughter, Adrienna, behind in Oakville in order to train with his present coach, Dan Pfaff, at Louisiana State University.
"I basically took it on as a job," he said. "I was going to work really hard in '94 and see where it took me."
It took him to Gothenburg, where he took the world title off Christie; then to Atlanta, where he defeated the pre-race favourites, Ato Boldon and Frankie Fredericks.
If star status needs to be bedded in achievement, Bailey has what is required. He is a quirky, intelligent individual. And while he has a background in marketing and a meticulous approach in common with Johnson, there is a twinkle to him which is absent from the American. At times, you can sense him delighting in stirring up mischief.
Last year, for instance, he smiled broadly at a press conference in London as he contended that Linford Christie had faked injury in the previous year's World Championship final.
He levelled the same accusation against Johnson in Toronto, clearly offending the American with the brutal directness of his accusation - "he knew he was going to get hammered after the first 30 metres."
The effect was not mitigated by the subsequent, diplomatic statement from the Bailey camping wishing Johnson a speedy recovery from his injury.
Johnson may still argue that that unofficial title of world's fastest man is undecided, given that he failed to last the course in Canada.
Bailey also appears to have gone back on his immediate dismissal of any re-match with Johnson - yesterday his agent, Ray Flynn, said he was "totally serious" in proposing a re-match later this year in a Las Vegas parking lot.
"There has been a great deal of interest shown in a rematch and I think the people supporting Michael Johnson would be very keen on another race as their man did not do himself justice in Toronto," Flynn said. "You can lay a Mondo strip of track anywhere and if the money was right, a parking lot at one of the big Las Vegas hotels could be the ideal place to stage the race."
Yesterday, Bailey dropped another contentious comment into the conversation when he put forward the case for Christie re-thinking his decision not to compete in this summer's world championships.
"Linford is still fast enough and consistent enough to be there," Bailey said. "He comes out and puts in the performances year after year. You have to respect the guy's decision, but I think he should finish his career at the World Championships.
"People go on about his age but Linford never shows it. Don't expect me to be still running at 37 - I'll be playing golf or something.
"One day I'll decide that's it. I'll give this thing the biggest shot possible and then I'll walk off. It won't be in 10 years or eight years' time - it will be less than that."
The story goes that soon after his Olympic victory, Bailey was refused entry to a Toronto nightclub. "Don't you recognise who I am?" he asked.
The case is altered for him now - certainly in his home country. After his win over Johnson on the eve of Canada's general election, the front page headline on the Toronto Sun newspaper read: Bailey for Prime Minister.
With Johnson absent from this summer's world championships - unless a late and unprecedented wild card should be produced by the international federation - Bailey has the chance to run the show himself. The chances are he will revel in it.