In many ways, Liverpool may be about to find themselves back at the crossroads they once stood at more than 15 years ago, should owners Fenway Sports Group decide the time is right to sell up at Anfield.
It was back in the mid-2000s when late owner David Moores reluctantly accepted that he simply did not have the wealth to keep the club he loved atop of an English game that was radically morphing into the Premier League product that we know it as today.
As the likes of Chelsea - backed by billionaire Roman Abramovich - and Manchester United - whose success on the pitch underpinned their ability to spend off it long before the Glazer family took over - continued to spend large sums of money on the pursuit of progress, Moores, with the heaviest of hearts, decreed that a sale was needed.
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"You only sell the family silver once," was the famous phrase uttered by the one-time Liverpool owner. Almost 15 years on from the eventual change of hands to Tom Hicks and George Gillett, FSG, albeit on a different scale, have maybe reached that same point of their Anfield stewardship.
The news that the Boston-based group have retained the services of major US banks Goldman Sachs and Morgan Stanley to explore their options is a significant step. The statement that followed spoke of their openness to third-party investors and potential new shareholders, while stopping short of confirming a full-blown search for a buyer is underway.
“There have been a number of recent changes of ownership and rumors of changes in ownership at EPL clubs and inevitably we are asked regularly about Fenway Sports Group’s ownership in Liverpool,” read the message.
“FSG has frequently received expressions of interest from third parties seeking to become shareholders in Liverpool. FSG has said before that under the right terms and conditions we would consider new shareholders if it was in the best interests of Liverpool as a club.
“FSG remains fully committed to the success of Liverpool, both on and off the pitch.”
The timing is significant, even if it's not necessarily a decision that has been shaped by just a poor start to the campaign by Jurgen Klopp's side. With the Reds sitting in eighth in the table, most of the clubs above them have the kind of resources that FSG simply cannot compete with under their strictly self-sufficient model.
At a time when they are trying to claw back points deficits to teams owned by the likes of the Public Investment Fund of Saudi Arabia (Newcastle) and Sheikh Mansour of the United Arab Emirates (Manchester City), it has become increasingly difficult to keep pace at the top of English football.
Throw in the aggressive and upwardly-mobile ownership of the Todd Boehly-led consortium at Chelsea and Manchester United's enduring financial power and it's clear FSG will need to revamp their approach towards spending if the good times are to continue into the final years of the Klopp era.
The Reds manager has spoken, if only briefly, about the desire for more risks to be taken in the transfer market, but for reasons only those inside the corridors of power will truly know, Liverpool have been unable to furnish their squad further.
Perhaps there was no more glaring example than the deadline-day dash to bring in Arthur Melo on a season-long loan as a belated reaction to an injury crisis in midfield. The Brazilian has played just 13 minutes in a Reds shirt before suffering a long-term thigh injury.
With midfielders like Naby Keita, Alex Oxlade-Chamberlain and James Milner out of contract in the summer and Jordan Henderson and Thiago Alcantara both in their 30s, a complete overhaul of the engine room is likely to be required sooner rather than later at Anfield. Do Liverpool have the funds necessary to do that under the FSG model? A lack of Champions League football next season would surely suggest not.
Instead, perhaps what John W Henry and the rest of the Fenway group have considered is that the ideal time to pursue a sale is now. With the Anfield Road development project heading into its final months, a new dawn for one of the most iconic football stadiums on the planet is fast approaching.
Add that to the other infastructure projects completed on FSG's watch - the £110m Main Stand and £50m AXA Training Centre - and the Americans can proudly point to three major pieces of investment as their bricks-and-mortar legacy, wherever and whenever their final days as owners arrive.
On the pitch itself, the appointment of Klopp in October 2015 was the turning point for it all at Anfield. The Reds have won every top-level trophy available to them during the German's tenure after assembling a world-class squad capable of challenging for all the honours going - quite literally where last season is concerned.
Mistakes have made along the way, of course. The decision to use the UK Government's Furlough and Job Retention Scheme at the start of the coronavirus pandemic was ill-judged and quickly rectified, while a U-turn over the plot to push ticket prices up to the £77 barrier in 2016 also had to be taken.
The idea to trademark the name of the city itself was another misstep and the plan to sign up to the doomed Super League was an embarrassing yet mercifully short-lived episode that ended with a public apology from Henry in April 2021.
On the whole, though, their stewardship must be viewed as a successful one, whenever the end of the line is reached. Like Moores two decades ago, it seems there might just simply be a realisation that the current level of investment can only take Liverpool Football Club so far.
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