When another Scot, Peter O'Rourke, guided the club to FA Cup final success over Newcastle in 1911, the Newmilns native was at the helm during one of the most memorable chapters in the Bradford story. By the time Jefferies moved into the hot-seat at Valley Parade in November 2000, the Yorkshire outfit was on the bones of its backside.
With the kind of lavish excesses that used to be the sole reserve of insane Roman emperors, Geoffrey Richmond, the former chairman, embarked on, what he later called, "six weeks of madness" in an attempt to preserve Bradford's Premiership status. Big money signings like Benito Carbone, Stan Collymore and Dan Petrescu were all paraded in the claret and amber but the financial gamble came at a huge price and the ravaging effects are still being felt to this day.
Jefferies was the man brought in to aid the salvage operation, against a backdrop of savage financial cuts, and having failed to keep Bradford in the top flight come the end of 2001, he jumped from the sinking ship on Christmas Eve of that year.
This weekend, after two bouts of administration, various flirtations with the footballing grim reaper and relegation to the fourth tier of the English game, Bradford will taste the high life again when they contest the Capital One League Cup final with Swansea City at Wembley.
Jefferies' time in this former textile town may have been short-lived and sour but the Dunfermline Athletic manager has no regrets and will be keeping an eye on proceedings when his former club aims, once again, to go from underdogs to top dogs against Premier League opposition.
"It was a chance to manage in the Premier League and we [with his assistant, Billy Brown] couldn't turn that down," recalled Jefferies, whose managerial stock had been on the rise since he steered Hearts to Scottish Cup glory in 1998. "I'll never regret going there, it was just a bad time. It was a survival job and the remit was to reduce the wage bill but we couldn't turn it around. The next season we were promised the chance to build. He [Richmond] took us to lunch and promises were made that never materialised. But the club itself and the people around it were fantastic."
In a proud, 110-year history, it is the last 30 that have shaped Bradford City. The devastating fire of 1985 that ripped through the main stand and left 56 dead will never be forgotten while the financial foolhardiness that threatened the club's very existence has only strengthened the resolve of those who hold City dear.
"You cannot write them off," added Jefferies, of a team that has already beaten Wigan Athletic, Arsenal and Aston Villa en route to a first major cup final in 102 years. "We always use that phrase in football, 'their name is on the cup', and it might well be true for Bradford. This club has been through a lot over the years and there is a great spirit because of what has happened. They deserve everything good that comes their way. It is a big club with a big fan base and winning on Sunday would be a fantastic achievement."
Given that Bradford have won their last nine penalty shoot-out showdowns in cup competitions, it's perhaps not surprising that Jefferies' judgment on this bout between the Bantams and the Swans is coloured by the spot-kick.
"I was going to say 2-1 to Bradford," he concluded. "But I wouldn't be surprised if they won on penalties. In fact, I'll stick a tenner on that now."