The biggest period of Eisner's Portsmouth ownership: everything at stake in transfer window

In a campaign where the invigorated vibrancy of Pompey’s training ground has been a hallmark of their success, the island air was weighing heavy.

Given the upbeat mood of the club’s Hilsea base this term, the disappointment descending as news of Alex Robertson’s likely season-ending injury was digested was understandable  - but nonetheless jarring.

Boss John Mousinho was putting a brave face on the loss of a second central figure, but his demeanour told a slightly different tale as news of the extent of the Aussie’s serious hamstring tear permeated.

Meanwhile, the mourning of Robertson’s loss was sweeping across social media with the depressing news confirmed to the online masses via official channels at 2.45pm.

The desperate reaction and swathe of bleak memes was wholly anticipated and, on this occasion, more than justified.

Robertson joining Regan Poole on the injury list has shorn Pompey of arguably their two best players. While Poole carries out his rehab here, the mercurial Aussie has returned to his Premier League parent club for his rehabilitation - erased from the season from here on in.

This, need we be reminded, comes against a backdrop of one win in six games in all competitions with a seven-point lead evaporating over a Christmas period redolent of opportunity.

We, of course, have been here before.

Our glass-half-empty minds are transported back to table-topping Christmas periods in 2018 and 2020, with capitulations following off the back of disappointing January recruitment.

Those with slightly longer memories, however, can recall one of the greatest seasons in the club’s history, which emerged from a bleak winter of discontent 22 years ago.

A single win from seven Division One fixtures at this time of year has been airbrushed from the 2002-03 season, long forgotten amid the championship-winning glory which was to follow.

Harry Redknapp’s juggernaut started to stall, stutter and was in danger of completely breaking down. A Steve Stone service, Tim Sherwood MOT and Yakubu fuel injection later and Pompey were on the fast track to the Premier League.

Three years later, and it was the January investment under Sacha Gaydamak which allowed an eight-point gap from safety to be turned around in the new year. The Great Escape wouldn’t have been completed without the wonderful Andres D’Alessandro, Benjani and that Spurs trio of Pedro Mendes, Sean Davis and Noe Pamarot arriving at this juncture.

So this is the crossroads we find ourselves at once again under the guidance of Michael Eisner.

In a period where there’s been a fair amount of panic and even a degree of hysteria, it’s no overstatement to say we’ve now arrived at the most important moment of their six-and-a-half year Pompey stewardship.

The support, we are told, will be forthcoming over the coming weeks - finding the right solutions to the problems presented a trickier challenge.

This, of course, is where sporting director Rich Hughes comes in. The man with a burgeoning reputation enhanced by a Pompey transfer Midas touch over the past 12 months, now has to do it all again.

While the rest of us do our Football Manager transfers, the man from Staffordshire has to deal with the realities of operating in a winter window.

That includes targets climbing their way up the pecking order and back into first-team favour at Championship level, their current employers loathe to leave themselves short of options.

That means foes in League One outright refusing to countenance dealing with a rival for their prized assets, when they’re vying with them for a place in the second tier.

And it guarantees sides at a lower level sticking the ‘Pompey tax’ on valuations when the enquiries arrive for their talent.

Meanwhile, when it comes to under-21 level, it’s a case of firstly finding the right profiles of players who can make a difference and have the blend of attributes sought - pace and power out wide, for example.

Crucially, then comes handling the demand of not only playing for Pompey, but being plunged straight into the middle of a high-stakes title chase at Fratton Park. For all of Hughes’ transfer magic, those players aren’t spilling out of every nook and cranny of a Premier League academy.

The good news is confidence in the process isn’t misguided.

Hughes’ transfer stock thus far remains high after his shrewd business. Meanwhile, the Pompey football operation are confident a request to loosen the purse strings for the right opportunities will be considered favourably. That is not to say, however, the coming days and weeks will not be fraught with transfer difficulties.

At this stage the picture will not be clear with the moving parts of international absentees, Cup commitments and the wait for the transfer domino rally to start the narrative in earnest. It would be easy to be unsettled, while the rest of us lose our heads.

Pompey know they have to get this right, but it’s also abundantly clear they have to hold their nerve: the stakes are at an all-time high under the Eisners - but so are the rewards.