Michael Appleton sat at the Marriott hotel bar, sipping on a large coke.
Soon he may have wished he was drowning his sorrows with something considerably stronger.
For on that wet and windy November 2011 evening, his Pompey ambitions imploded.
Today, Pompey remain bandaged and bedridden after being caught head first in that ferocious blast.
As for Appleton, he is now convalescing in Blackpool having got himself a transfer this week.
In his absence, Fratton Park staff have been told to expect another round of redundancies.
And the creation of the tornado still swirling around Pompey can be traced back to Thursday, November 24, 2011.
That very same night I was invited for a relaxed evening with the new manager of the Blues.
It was the opportunity to meet in a social environment to forge a positive working relationship.
The Marriott was the preferred venue considering Appleton was staying there ahead of renting a place in Winchester.
I was alone as I walked into the North Harbour hotel on that fateful night, although I did come with a snippet of breaking news.
For that very evening, Vladimir Antonov had been arrested on charges of alleged fraud.
The chairman of Pompey was assisting with an investigation into allegations of asset stripping at Snoras Bank.
It was all over the news, Twitter and message boards. Clearly the jungle drums hadn’t been heard at the Marriott, however.
Pompey’s manager had never met the leading shareholder in CSI and his employers for the past 14 days.
Yet now he knew plenty.
Having delivered this interesting instalment in the long-running soap opera in person to Appleton, I witnessed a wry smile crack across his face.
Perhaps it was the dawning of what he had let himself in for, perhaps it was a failure to truly comprehend the severity of the situation.
It was the first instance of a reaction many of us would see regularly over the next year.
Publicly, Appleton would leap on to the bombs and smother them rather than running for cover screaming. With a shrug of the shoulders he would simply tolerate such a hand and carry on with his duties with a steely determination.
In fairness, neither of us could have foreseen almost a year later Antonov’s innocence or guilt has still to be established, while Pompey would remain entrenched in administration.
Regardless, it would prove the seminal moment which demolished Appleton’s five-year plan.
Not that it distracted him too long during the subsequent off-the-record conversation.
Here was a clearly-perceptive man who during his first two weeks at the club had already swiftly comprehended what he had inherited.
He had assessed Tal Ben Haim needed disposing of, for a start.
A tiresome presence in the dressing room and unpopular member of the playing squad, Appleton had already hauled off the Israeli at half-time at Watford.
The boss’ plan was to remove him from the club as soon as possible and had been reassured by senior players such moves would not fracture the squad.
Of course, Appleton would soon discover that was a little more difficult than he had anticipated.
Appleton spoke of his initial concerns over the effectiveness of David Lampitt, ironically the driving force to bringing him into the club.
To describe the chief executive’s relationship as highly fractious with Appleton’s predecessor Steve Cotterill would be something of a dramatic understatement.
Appleton queried the commitment – and ability – of Aaron Mokoena, raised the idea of Jason Pearce as club captain and debated Joel Ward’s best position.
However, it was when discussing the future that his eyes truly shone.
Appleton had been given the chance to mould a football club from bottom to top in the very image he saw fit.
He had been promised time, financial backing and the freedom to initiate a five-year plan to flatten and then regenerate.
It was an enticing proposition for somebody who had clambered his way up through the youth coaching ranks at West Brom to become the future England manager’s right-hand man.
It was his dream opportunity.
Avram Grant was a cruise-control manager who relied heavily on others to drive him, Paul Hart was King Kong let loose in New York, Steve Cotterill was obsessive, unpredictable and volatile.
Appleton was a forward-thinking Pompey boss steeped in honesty, integrity and a willingness to trust .
Five days after that Antonov bombshell, CSI entered administration.
On February 17, 2012, the club went into administration – where they remain to this day.
Circumstances dictated we can never accurately judge Appleton’s ability as a manager.
But what is certain, the arrest of Antonov was as devastating for him as it was for the club he had been managing for just 14 days.