Stewart, currently the Labour-supporting director in West Lothian, has already been stitched up by the SNP in west Fife newspapers, a state of affairs not unrelated to personal rivalries on his current patch. He was previously head at Inveralmond High in Livingston.
By sheer fate the West Lothian-Fife connection is about to spill over into another potential frisson - which also has its origins in a Livingston secondary.
One of the long-running internal battles was Stewart versus Gavin, or Tony of the parish of St Margaret's Academy. Gavin retired as headteacher last summer and was one of the most formidable Catholic leaders - honoured by Her Majesty, no less, for his services.
He was not afraid to speak his mind and strayed into serious trouble two years back. After complaining through the pages of The TES Scotland about unfair council spending allocations to schools, he was subsequently disciplined for breaking the authority's code of silence. But he did not take kindly to being hauled over the West Lothian coals by a director who was once a fellow Livingston head.
And so to more fickle fortunes. Gavin has retired to his home in Fife to improve his golf swing while keeping his hand in as an educational figurehead.
As luck would have it, he is now the Catholic Church representative on Fife's education committee where he will be free to criticise on any matter he sees fit.
Fate, dear boy, fate.