Few lines in English literature are more devastating than John Milton’s description of Satan in Paradise Lost. Cast out from Heaven, condemned to defeat, Satan consoles himself with a final act of pride. If he cannot possess paradise, he will at least possess power. Better an inferior kingdom that he controls than a superior one in which he must share authority.
It is a warning about a particular type of leadership. Not leadership that fails through incompetence. Leadership that fails because it cannot tolerate rivals, leadership that values control over achievement. Leadership that would rather dominate a diminished realm than surrender influence in pursuit of something greater.
THE CELTIC FAMILY- DESMOND & CO
For some Celtic supporters, that passage has become an uncomfortable way of understanding the modern history of their club.
Yet for much of Dermot Desmond’s tenure as the club’s controlling shareholder, Paradise has seemed curiously content with its limitations. Domestic dominance has masked persistent European underachievement. Elite managers have arrived, transformed the club and departed. Lessons have been repeatedly ignored. Temporary solutions have become permanent strategies. The overwhelming impression is not of a club relentlessly pursuing excellence, but of a club repeatedly choosing the safety of control over the risks required for genuine progress.
The strongest criticism of Desmond begins with Europe.
For all the domestic trophies accumulated during his tenure, Celtic’s record in qualifying for and competing in the Champions League remains profoundly disappointing. Individual failures can be explained away. Football is unpredictable and even the best-run clubs suffer setbacks. The problem is not that Celtic have occasionally failed. The problem is that they have repeatedly failed in remarkably similar ways.
Time and again the club has entered crucial European qualifying campaigns looking underprepared. Recruitment has been delayed until after decisive fixtures. Obvious weaknesses in the squad have remained unresolved. Managers have entered pivotal matches without the personnel they requested. Qualification is lost, explanations are offered, lessons supposedly learned and promises made.
Then the cycle begins again.
What is striking is not the failure itself but the club’s apparent inability to learn from experience. Successful organisations develop structures that prevent the same mistakes recurring. Celtic have often looked like a club trapped within a permanent state of improvisation, where every European disappointment is treated as an isolated event rather than evidence of a deeper structural problem.
For a club with Celtic’s resources, support and ambitions, that represents a significant failure of governance. Responsibility for governance ultimately rests at the top. It rests with Desmond.
The same pattern can be observed in the club’s relationships with managers.
Celtic have twice, in recent years, identified coaches capable of transforming the organisation. Brendan Rodgers elevated standards throughout the club and delivered unprecedented domestic success. Ange Postecoglou inherited a club in turmoil and rebuilt its identity with astonishing speed. He restored excitement, improved recruitment and reconnected supporters with a clear footballing vision.
Both managers succeeded.
Neither manager stayed.
Of course, there are mitigating circumstances. Leicester City and Tottenham Hotspur offered opportunities that few coaches would reject. Scottish football cannot compete financially with the Premier League. Yet this explanation only goes so far. The real question is why Celtic repeatedly appear unable to create an environment in which elite managers believe their future lies at the club.
The answer may simply be economics.
Critics, however, suspect something more fundamental.
CELTIC- WHERE THERE IS A FEAR THAT SUCCESS COULD ASK AWKWARD QUESTIONS OF THE STATUS QUO
Rodgers and Postecoglou were not merely coaches. They were leaders capable of reshaping institutions. They possessed strong ideas, strong personalities and growing authority. Success inevitably increases managerial influence. Truly elite coaches do not simply operate within existing structures. They change those structures.
That brings us back to Milton.
Some supporters have come to believe that Celtic under Desmond are more comfortable with managers who fit within an established hierarchy than with managers capable of challenging it. From this perspective, the recurring friction between strong coaches and the club’s power structure is not accidental. It is an inevitable consequence of a model that prioritises centralised control.
Again, this is interpretation rather than fact. Yet it is an interpretation that helps explain a puzzling reality. Celtic repeatedly discover high-calibre managers. Those managers repeatedly improve the club. Those managers repeatedly depart before their projects reach full maturity.
The issue is not identifying talent.
The issue is living with the consequences of it.
This tendency may also explain the club’s repeated reliance on interim appointments.
Interim managers often enjoy immediate success because the circumstances are unique. Expectations are lower. Players receive a psychological lift. Supporters unite behind a familiar figure. Short-term improvement frequently follows.
The mistake is assuming that short-term success proves long-term suitability.
THE RETURN OF NEIL LENNON HIGHLIGHTS THE FEAR OF PUSHING BOUNDARIES
Neil Lennon’s appointment in 2019 remains the clearest example. Lennon successfully stabilised the club following Rodgers’ departure and delivered immediate results. However, the decision to make the appointment permanent reflected emotional momentum rather than strategic thinking. The subsequent collapse of the ten-in-a-row campaign exposed weaknesses that had been masked by the initial bounce.
The lesson should have been obvious, the skills required to rescue a situation are not necessarily the skills required to build an enduring elite football operation.
Yet Celtic’s leadership has often appeared attracted to familiar faces and reassuring solutions. Having benefited from successful interim appointments, the club seemed to convince itself that the success of the caretaker period automatically justified a permanent appointment. The distinction between solving a short-term crisis and building a long-term future became blurred.
That confusion reflects a broader weakness. Again and again Celtic have seemed drawn towards decisions that prioritise continuity, familiarity and control over ambitious strategic planning. Rather than seeking the disruptive challenge of elite leadership, the club has often appeared more comfortable with managers who fit the existing culture.
KEEPING THE HANDBRAKE ON AGAINST PROGRESS
That, ultimately, may be the central criticism of Dermot Desmond’s stewardship.
Celtic have never lacked resources. They have never lacked support. They have never lacked access to talented managers. Instead, they have often lacked the institutional self-awareness required to maximise those advantages. Recruitment failures recur. European disappointments recur. Managerial departures recur. The same problems emerge in different forms, season after season.
Every football owner makes mistakes. That alone cannot define a legacy.
What defines a legacy is whether those mistakes lead to learning.
For many supporters, that is where Desmond’s stewardship falls short. Domestic dominance has often disguised deeper weaknesses. Celtic have remained Scotland’s strongest club while consistently falling short of what their size, history and potential should allow them to become.
Which brings us back to Milton’s famous line.
Nobody seriously suggests that Dermot Desmond wants Celtic to fail. The accusation is more subtle than that. It is that for more than two decades he has built a club in which retaining ultimate control has too often been prioritised over creating the conditions for sustained excellence. Better to remain the undisputed power within a club that falls short in Europe than to share influence with the elite coaches capable of changing its trajectory.
It is impossible to prove. But it is increasingly difficult for many supporters to ignore.
RINSE AND REPEAT- THE CELTIC WAY
And so the great irony of the Desmond era is captured by the very book from which this article takes its name. In a stadium called Paradise, the club has spent years chasing ambitions that always seem just beyond its reach. Not because the talent was absent. Not because the resources were lacking. Not because the opportunities never appeared.
But because, at every critical moment, Celtic seemed more comfortable ruling a smaller kingdom than building a greater one.
Paradise, in other words, was not taken away.
It was lost.
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