In need of an expensive rebuild under their visionary overseas coach, Liverpool decided a minority investor was the best solution in order to compete for the Premier League and Champions League.
Their recently appointed chief executive, Rick Parry, had a plan, identifying the benefits of a strategic partnership with a media giant - one who inherently understood Anfield culture and would add value to the company as it moved to untap the resources of the strange but still largely unknown territory called the ‘world wide web’.
Step forward north-west based Granada TV, whose chief executive, Steve Morrison, was a passionate football supporter and whose parent company, ITV, dreamed of wrestling back live top division broadcast rights from Sky.
In 1999, Granada paid £21 million for a 9.9 per cent stake in Liverpool. They would invest a further £20 million for a 50 per cent share of the newly formed liverpoolfc.tv to expand the club’s primitive media operations. With the signing of a hefty cheque, Liverpool moved from analogue to digital overnight.
Over the following months, Liverpool’s manager Gérard Houllier broke the club transfer record for Emile Heskey and signed Dietmar Hamann, Sami Hyypiä and Markus Babbel - players who would become the core of the 2001 treble-winning team. Liverpool would compete on Europe’s biggest stages for the rest of the decade.
Granada’s cash injection facilitated that new era, and there are obvious echoes in what John W Henry and Fenway Sports Group are hoping to achieve in their current pursuit of a minority investor.
FSG wants a partner to add value, which is why the big media beasts are so attractive and Henry is understood to have spent recent months actively courting some of them. He might strike gold if there are those with a long-term strategy to compete with Sky, BT and Amazon for Premier League and Champions League rights who see the benefit of representation on a Premier League board. Rather than buying a football club, dipping their toe in the water so as to be well-placed to react to favourable market conditions before the next bidding war might be a calculated punt.
At the start of the Millennium, ITV were eager for a seat on the Anfield board, and later paid £27 million for a five per cent stake in Arsenal, partially to ensure they would not be wrong-footed as Sky hovered menacingly around Manchester United. It was unpalatable for a broadcast rival to yield so much power and influence.
The grim warning from history is that such ambitions were thwarted when ITV Digital - launched as a competitor to Sky by offering live Champions League games - swiftly lost its war with its established subscription rival. ITV Digital went bust in 2002, and by 2003 the executives who had launched the move into football had left Granada as the company tried to pull the plug on what it considered ill-advised ventures.
Granada never got their full investment back, the deal proving more profitable to Liverpool than its partner.
Aside from Houllier’s spending spree, there was a legacy of attractive spinoffs for Liverpool. Official club media was in its infancy in 1999, generally amounting to whoever was responsible for writing the matchday programme or updating the clubcall voice messages, when fans would pay a premium rate to hear if Vegard Heggem was still an injury doubt for the weekend.
The big six still dreamed of individual TV rights prompting supporters to flock to dedicated club TV channels or to watch live games streamed online, still blissfully unaware of how much of a red line that would be to future Premier League clubs who were still ploughing on in the Championship.
Twenty-four years on the ship may have sailed on any prospect of club media screening live domestic and European games, but the appetite to evolve the money-making potential of club websites, social media and TV channels is more insatiable than ever.
A 9.9 per cent stake in Liverpool today is more likely to cost around £300m
Where the biggest clubs face a dilemma partnering with a media giant is ensuring the superstars at their training ground understand the additional demands on their time in the event of an expanded in-house production department rocking up.
Klopp might welcome such a source providing the funds to bid for Jude Bellingham this summer, but given the extensive and what he occasionally considers irritating demands on his time from the media - especially on a matchday and what is known in his trade as matchday minus one - will he and his players be receptive to allowing greater access?
The timing of a new committee being set up by the Premier League to weigh the financial merits of offering greater ‘access all areas’ content ahead of the next TV rights auction adds to the intrigue.
Many Premier League clubs will naturally want everyone to share from the same pot, while the big six will be deliberating going alone believing with the right execution they can lure more of their own loyal subscribers rather than offering it to Sky, BT or Amazon. A high-profile media company as a shareholder will change the dynamic of that debate.
A 9.9 per cent stake in Liverpool today is more likely to cost around £300 million. Whether a strategic media partner will see this as a starting point for a full takeover, the basis from which to buy Premier League TV rights, or a means by which to revolutionise the club’s publishing and broadcasting output, Klopp will hope it leads to a golden outcome as he embarks on his summer squad reconstruction