Now before I proceed, a disclaimer.
Pressley and I have previous.
Three months into my first ever post in journalism ("The Weekly News") he got a bit upset because I reminded him of what he wrote in a Hearts matchday programme (he let it slip in his column that he played Championship Manager in his spare time - hard-hitting I know).
He demanded my then-boss "sort me oot".
My gaffer at the time (after suppressing his laughter) replied: "See You Next Tuesday".
That out of the way, I'll digress with what you the reader may regard to be a petty rant or a fair summery of Mr Pressley's 'leadership qualities'.
Despite being tipped by 'those in the know' that a bright managerial career was within his capabilities, it would seem that his ability to coach comes second to those two railroad workers in Blazing Saddles' attempt to get themselves out of quicksand.
If we include his assistant coach duties during his short spell with the Scotland set up, for a man dubbed 'coach with potential' his managerial CV is not exactly one that cries "I am successful".
Unless of course you add 'self promotion' to what a great manager should have.
You can't fault him on that.
Actually you can because beneath the 'tactical knowledge' is patter that would have a second-hand car salesman fearing for his job.
There's no doubt in his ability to give a good press conference.
But maybe he be more suited to punditry because it's one thing saying what should be done on the pitch - it's another to actually implement it.
Forty-two years ago yesterday, Liverpool appointed a manager who was not the best in terms of 'media communication' but by God Bob Paisley could manage a team to success.
Hot air without anything to back it up with does make others question why you're wasting your time with football.
Mr Pressley falls into that bracket.
His spell on the backroom staff of George Burley's disastrous reign as Scotland manager was marred with a failure to gain the respect of players.
Lee McCulloch in his autobiography remarked how Pressley did not command the authority that fellow coaching staff member Terry Butcher had. The latter would be able to let the players know who's boss while Pressley was either ignored or mocked.
If we go back into his playing career, a lack of astute leadership can be found there.
You remember the chaos at Hearts which led to the infamous 'Riccarton Three' press conference in 2006 criticising the way in which Vladimir Romanov was running the club?
While you would have had sympathy for the stand that Pressley (along with Paul Hartley and Craig Gordon) took, anyone within the hierarchy of a trade union would have been wincing at the tactics employed against the beleaguered trio's wage-payer.
If we assume that all forms of negotiation had broken down (and it was suggested that none had been activated as the conference was a knee-jerk reaction to a Romanov dressing room rant), then a meeting with Hearts players in the PFA Scotland union should have been called.
Namely to discuss and, if required, vote on industrial action.
It's what workers in other unionised workplaces do as calling an impromptu media conference to slag off the boss (tempting though that might be) would more than likely backfire with the end result being the sack.
Which is what happened to Pressley.
Heroic stands are one thing but stupid ones only serve to keep those you are railing against in the hotseat.
After all, you never see a top poker player reveal his hand after the first dollar has been bet.
Alas, he wouldn't learn the valuable lesson of picking and choosing his battles - his first full-time managerial gig at Falkirk showed that.
Now you could argue that his public boasts that "Falkirk are not getting relegated" back in 2010 was done to gee up his own players.
Even a later claim of "Everyone wants Falkirk relegated" might have been thrown out there to foster a siege mentality amongst his players.
Problem was, others involved in that season's relegation battle were also listening and Pressley's words made the team-talks of the then St Mirren and Kilmarnock managers (Gus MacPherson and Jimmy Calderwood respectively) very easy indeed.
Both were fired up and both duly relegated Falkirk - Kilmarnock especially with their final day escape.
Not surprisingly, Jimmy Calderwood had a thing or two to say about Pressley's big mouth:
"He came out with some things about colleagues.
"It didn't go down too well I can tell you that.
"People talk in football but I don't think Steven did himself any favours with his comments.
"We think we've got a wealth of experience here with Jimmy (Nicholl), Sandy (Clark) and I. But they have Alex Smith who has more than us put together and maybe it would be better if Steven listened to him a bit more.
"He's not helping his team or his club because it gives us extra motivation.
"He said they had more bottle than the rest. I know what I would have done if I was a player - I know what I did as a manager.
"Did we pin it on the wall and use it? What do you think? Listen, I don't know if it's a lack of respect, perhaps more a lack of experience.
"He did a few things as a player too. He was a great captain at Hearts but he went back to Tynecastle with Celtic and started kissing the Celtic badge.
"It's not very clever. But we've all done daft things."
So much so that Henry Winter of the Daily Telegraph listed him as one of 20 football people who helped make 2013 "a year to remember".
Admittedly, he had stabilised the ship at Coventry City who had looked like being cast adrift during administration, a points deduction and being made temporarily homeless.
However, within a year it would turn sour and his infamous lack of being able to hold his tongue would cost him big time.
Coventry had suffered a shock FA Cup defeat to non-league Worcester City.
A bad result and they happen - Coventry know that having had a cup exit to non-league Sutton United that is always being played on an FA Cup TV montage.
Back then, the manager at the time John Sillett took the Sutton loss on the chin and moved on.
Pressley though was to take a different tactic. He was going to show the cameras how tough a manager he was.
The post-match rant in all its glory follows:
“An incident occurred after the game - which I won’t go into – that told me all I need to know about certain players. They’ll be gone; they’ll be banished from this club.
“Worcester wanted it more and that has never been said of one of my teams, never. And it will never be said again.
“Certain players are in a comfort zone and they’ll be gone from this football club, make no mistake, they’ll be gone.”
“There was a frank meeting yesterday where fingers were pointed and players were told exactly how it is at this club. I will not defend them anymore.
“I defend these players with my life, all the time, but not anymore because certain individuals are not giving me, or the club, that back.
“I cannot sleep right now because I’m so angry about Sunday’s performance. I'm so angry that we embarrassed this proud football club and everything we try and do at this club. I can’t tell you how angry I am.”
Threatening to chuck players out six weeks before a transfer window opens was not a good move.
Had said window been days away from opening, Pressley could have done this and brought in new blood within a week or two.
However, he would have to try and motivate players to get valuable league points having said he would "banish them".
Not surprisingly, between that cup exit and Pressley's own from the club three months later, those threatened with banishment could only motivate themselves to gain 13 points from a possible 45 for a man who had delivered a scathing character assassination of them on live TV.
And so to Fleetwood where he barely last a year. The club's official statement spoke of wanting to move in a different direction.
Namely any other direction than the one they felt their soon-to-be former manager was taking them on.
Nevertheless, it is another 'failure' to be chalked up on the less than successful CV.
He'll probably talk his way into another management role - after all, he's good at that.
But it won't be long before word gets round that the man who palms himself off as Gus Hedges is more like Gordon Brittas.