A question I've seen asked a lot on social media since the announcement was made that he is taking over as CEO of York City.
It should be said at this juncture that is not a new role for Jackie. It is effectively what he did at Partick Thistle and what he did at Dundee Utd before they brought in David Southern to effectively signal the end of the good times at Tannadice. None of this was well publicised but Jackie signed the players, did the deals and paid for things like nutritional experts and life coaches at both these clubs (Out of his own pocket)
When he went to York, the talks began almost immediately after being sacked at Dundee Utd (A move Steven Thomson would tell him last April was a mistake) and he turned down the Derry City job to go to York.
As an outsider looking in, it wasn't an easy task for him. A combination of Richard Cresswell and Jonathan Greening were undermining him from day one, bitching to the local press because they thought they would get the jobs he and Simon Donnelly got. Similarly, a lot of the players were on more than decent money for not much effort and were swanning about in big cars with bigger egos.
Jackie knew this had to change.
Relegation was sore but owner Jason McGill (One of the nicest guys I've met anywhere) had faith in Jackie but both knew a massive overhaul was needed and it would take time.
Bottom line though was results were not good enough and a 6-1 defeat at Guiseley was the final straw.
A statement was released and Jackie said he would see what happened in the away game v Braintree. This baffled me a wee bit and I asked what was going on? His reply was "Sometimes you just need to see who is behind you and who isn't"
A 1-1 draw followed (York conceded an 88th minute penalty) and so confusion reigned.
I had a feeling this wasn't the end. Even when Jackie announced he would be standing down.
So the CEO announcement didn't shock me. There is a strong relationship there between Jackie and owner and Jackie has an incredible amount to offer a football club (Dundee Utd sought a blueprint for the future from him way after they sacked him) so this kind of stuff is within his skill set.
Finally, I must declare an interest here. Jackie is a close friend of mine and someone I have a lot of time and even more admiration for. His knowledge of football is second to none whilst he remains a passionate Celtic man.
So remember that when you read this, I am not his PR man nor his publicist. I just always wish the best for him and always will, primarily because he gave everything in that hooped jersey.