Could this Celtic window get any more Upside Down? Stranger Things have happened.

Regular readers of this blog will know that I sometimes lean on pop culture references. I also dip into politics, history and the occasional odd analogy when I want to talk about Celtic.

For some people, that is exactly why they read this blog. For others, it is precisely why they don’t. Either way, I’ve always found these sidebars fascinating. I enjoy them, and I hope most of you do too, because we are heading off on another one.

Let’s be honest. Transfer windows are hard. At Celtic, they are brutal, and they have been for a long time. That is why Ange’s first summer window, and the winter window that followed it, stand out so sharply. They feel like small islands of quality, professionalism and achievement in an otherwise bleak and pitiless ocean of mediocrity.

During any transfer window, rumours inevitably race ahead of reality. That happens everywhere. At Celtic, though, supporters cling to rumours far more fiercely because, most of the time, rumours are all we have before disappointment arrives.

This is the club with money in the bank. This is the club sitting on a small fortune. Celtic remain the strongest club in the country and the richest as well. Yet we still fumble, still undersell ourselves, still sell ourselves short and, increasingly, look dreadful in the way we conduct our business.

Over the last few years, it has been impossible to avoid awareness of the Netflix show Stranger Things. Even if you have never watched a single episode, you will have some grasp of the basic concept. At the very least, you will know what the Upside Down is supposed to be.

In the show, the Upside Down exists as a parallel setting. Stranger Things unfolds in a small American town called Hawkins, while the Upside Down functions as its dark mirror image. It is the same place, but twisted into a different reality.

That is exactly how Celtic transfer windows feel almost from the moment they open. Two parallel worlds emerge. One is the world that should exist. The other is the one we end up panicking in before the window closes. In the Upside Down, everything resembles reality but feels skewed, warped and out of sync. That makes it an almost perfect metaphor for Celtic’s transfer operations.

On the surface, the club looks functional enough.

The process appears correct. Scouts identify players. Data and analytics get consulted. Clubs receive calls. Interest is declared. Negotiations begin. Occasionally, journalists get briefed about targets. From the outside, this looks like progress. It feels normal. This is what functioning football clubs do.

Then, inevitably, it all unravels.

Players fail to arrive. Deals collapse for strange reasons. Timelines disintegrate. A month shrinks into a fortnight. A fortnight becomes a week. By the time a week remains, everyone knows it is heading for deadline day, often right down to the final minutes. Logic flips on its head, and outcomes never resemble expectations.

At that point, the excuses appear. Bad luck gets blamed. Difficult markets get cited. Selling clubs dig their heels in. Players supposedly refuse to come to Scotland.

None of that is bad luck. It is system inversion.

Selling clubs hold firm because Celtic refuse to pay what it takes. Players hesitate because the club no longer projects ambition and will not offer elite-level wages. This is not misfortune. It is policy failure.

Time plays a crucial role in all of this. At Celtic, supporters constantly hear that they do not understand how transfers work. We get told the window has only just opened. We get urged to be patient. Meanwhile, decisions that require months of preparation get rushed at the last possible moment. Questions about suitability, willingness, valuation and affordability all end up answered under pressure.

The inversion works in reverse as well. Once Celtic know a player wants to come and a selling club is willing to deal, decisions that should take days stretch into weeks because approval has to run up the chain to Dermot Desmond. Known gaps in the squad get ignored until they turn into emergencies. Negotiations then take place with clubs who know Celtic are desperate and sitting on cash.

That is a football club operating in the Upside Down.

You can trace this pattern through December 2023, through this January, through both Brendan Rodgers exits and beyond. Nothing happens when it should. Everything happens too late to matter. Deadline-day business almost guarantees inflated fees or outright collapse. Still, Celtic never learn.

In Stranger Things, the Upside Down does not exist separately from Hawkins. It is created from it. The danger that leaks into the real world is, in a very real sense, self-inflicted.

As I said in The Enemy Within piece, Celtic’s biggest problems are not stronger rivals, difficult windows, aggressive agents, UEFA regulations, labour laws or exchange rates. Those are distractions. The real problems live inside our own house.

Mistakes happen, but bad decision-making corrodes everything. Most clubs secure replacements before selling key players. Celtic sell first and scramble later. Chaos follows. The dysfunction becomes so extreme that it turns even rational supporters into conspiracy theorists.

In the Upside Down, reality itself malfunctions. Compasses spin. Radios crackle. Light barely works. Familiar tools stop behaving as they should.

At Celtic, elite managers struggle when they should thrive. Recruitment fails regardless of who runs it. Mark Lawwell has gone. Paul Tisdale has gone. That points to policy, not personnel. Accountability barely exists. Good ideas die in committee. A museum never materialises. Stadium expansion never happens. Barrowfield gets diluted. Momentum drains away every single time.

Even capable people get dragged down by this environment. Urgency screams, yet progress sinks into quicksand. Every window, supporters tell themselves that the club must surely know it got the last one wrong. Every window, hope flickers briefly before reality returns.

And once again, we find ourselves staring across the same dark landscape.

In Stranger Things, the only way to win is to seal the breach. Hawkins suffers because a tear has opened in the fabric of reality. Killing monsters endlessly achieves nothing. Only closing the breach fixes the problem.

Celtic face the same issue. Changing scouts, heads of recruitment or managers does nothing to seal the breach. The club always ends up in the same place, rehearsing the same arguments and mourning the same failures. The people who could fix it refuse to do so.

That is the truth. The solution lies in new leadership. Not new managers. Not new scouts. New directors. New decision-makers. A new structure.

This increasingly feels like life inside a parallel universe. Worse still, that warped reality keeps getting presented as normal. A club of Celtic’s size should not operate like this, yet what we now resemble is a distorted mirror image of professionalism.

Too often, managers find themselves handed players they neither chose nor can realistically use.

Yesterday, Martin O’Neill spoke about Balikwisha, a player the club pursued for two years as a winger, only for him to point out the obvious fact that Balikwisha is not suited to playing wide. How the entire recruitment apparatus missed something so fundamental is hard to comprehend.

How did the entire apparatus miss something so basic? This is not a new problem.

I still remember John Kennedy having to explain the sale of Patryk Klimala. He pointed out that Klimala was a counter-attacking striker at a club that does not play counter-attacking football.

That explanation raises an obvious question. Why did Celtic sign him at all? Klimala played 28 games over 18 months and scored three goals. He never fit. He never belonged.

No one has ever properly explained that signing, and Klimala is not an outlier. Each of these decisions costs time, money and squad places. They all stem from a basic failure to ask the simplest question in football before signing a player: does he fit the manager’s needs?

Celtic fans do not deserve this warped reality. They do not deserve to watch their club subjected to this bizarre, self-inflicted experiment. They do not deserve a window drifting towards its predictable denouement and the effective derailment of a title challenge.

Of course, it is possible that I am wrong. Deals may be progressing quietly.

The club could yet modernise its structure and drag itself into the present.

I doubt it. I really do.

But in this version of Celtic, anything is possible.

Stranger Things have happened.

Just don’t get your hopes up.