Flynn is a high-flyer with lofty ambitions who is widely talked about as a potential successor to the first minister.
The SNP’s former Westminster leader was a commanding presence in the House of Commons, but his new role as a cabinet secretary is a whole different game. He has to be across a huge range of detail in an expansive brief.
Swinney is well regarded for a deeply technocratic approach to his politics. By that measure, Flynn stumbled at his transport committee appearance last month.
He was not across the day’s news on the Glen Sannox leak and, according to the emails revealed today, his office did not pass on the details of the leak story – despite receiving two emails.
Opposition politicians, who pounce with glee at any sign of weakness in a big political beast, suggest a touch of arrogance for the first part and a dysfunctional office for the second.
Transport Scotland has been clear – it says draft media statements do not constitute a briefing.
What’s more concerning for Flynn is: how this will be viewed within the party?
He certainly ruffled feathers in the SNP last year as he sought the Aberdeen Deeside & North Kincardine nomination. Some regarded his approach as heavy-handed and there’s maybe a certain amount of schadenfreude in the north-east today.
His loyal supporters will also be troubled by this unforced error from the man who could be first minister.