And from the leadership of Stirling Council, the General Secretaryship of the Scottish Labour Party, to Donald Dewar's first Cabinet, his mastery of Labour's machinery enabled him to emerge triumphant as First Minister of Scotland.
As Jack the Lad climbed the greasy pole he rarely looked uncomfortable, most notably on the occasion when he held a press conference to confess to marital infidelity. And even then he managed to ride the storm with relative ease.
Behind the scenes, his time as First Minister was marked by strife with then Chancellor Gordon Brown, but now we know that was hardly unusual. His was a largely smooth ascent but now he has gone the way of all defeated political flesh and taken his place in Westminster's upper chamber.
Once again cloaked in red, but this time with a slightly embarrassed flush to match, Lord McConnell of Glenscorrodale took his place in the House of Lords. As they might say in Arran, if Jack fell into the Firth of Clyde he'd come out with a salmon in his mouth.