Liverpool have enjoyed enormous success since Jurgen Klopp assumed the managerial role in 2015, and despite their recent struggles they have clinched major silverware across almost every available front with the German at the helm.

While the lion’s share of Liverpool’s transfer strategy in that time has been brilliantly executed, there is one particular missed opportunity which stands out as a major ‘what if?’.

According to The Athletic’s James Pearce (when he wrote for the Liverpool Echo), Liverpool were interested in a move for Dele Alli before the attacking midfielder completed an initial £5m transfer to Tottenham Hotspur from MK Dons in 2015, when he was only 18.

Alli went on to make 269 appearances for the Lilywhites, scoring 67 goals and supplying 61 assists, with the majority of his success coming in the earlier stages of his Spurs career before a spluttering finish to his time in north London resulted in a move to Everton after being pushed for an exit from N17.

Alli, who former Tottenham boss Jose Mourinho once backed to become “one of the world’s best”, plundered 37 goals and 29 assists across his first three Premier League campaigns, leaving pundits and fans waxing lyrical over the prodigious rate of goal contributions for a midfielder of such a tender age.

This season is a different story, though. Having been shipped out on loan to Turkish Super Lig outfit Besiktas by the Toffees, the 26-year-old has scored just three goals from 16 appearances, with a return to prominence on football’s biggest stages appearing an increasingly distant possibility.

For a once budding talent with the world at his feet and a ceiling stretching far beyond most up-and-comings prospects within English football, Alli’s plummet from prominence might seem inexplicable. However, an illuminating past report from The Athletic lays bare his regression, highlighting his stark decline in output and technical deficiencies as key components behind his fall from grace.

There were also question marks over his attitude and application, something that Mourinho infamously called out in one of his first training sessions as Spurs manager in November 2019.

Had he joined Liverpool in the summer of 2015, with the Merseyside outfit soon to appoint Klopp in the managerial role and duly opening the door to an illustrious period in the club’s history where Premier League and Champions League trophies were gleaned, it all might have been so different for the playmaker.

Klopp’s high-octane counter-pressing system, heaping emphasis on full-backs Andy Robertson and Trent Alexander-Arnold to serve as devastating, overlapping creative focal points, has been a largely unrelenting and formidable strategy.

With Alli receiving such superlative service in the form of precise looping crosses and swift, aggressive movements up the pitch, playing under the German could have given him the platform to truly cement an enduring stature as one of Europe’s most effective threats behind the frontline.

Alli’s downfall is largely down to his failure to adapt and maintain standards of performance for someone of his calibre, but if a demanding coach like Klopp could have had the chance to put his faith in the 37-cap Englishman’s abilities, he could have provided him the confidence needed to flourish at the top of his game for longer, rather than spiking so young before an alarming drop-off.

Alli’s early exploits with Tottenham serve as evidence that there is a player of immensely talented capabilities still laying dormant within, and despite his subsequent fall from grace, the 26-year-old boasts one of the most resounding entrances to the Premier League of any English starlet in the division.

Indeed, Klopp has previous when it comes to nurturing bright English talents, promoting Alexander-Arnold from the Reds’ academy and honing his talents to help the 24-year-old become one of the best right-backs in the world at his prime.

If only Alli fallen into Liverpool’s clutches around the time that Klopp came to Anfield, it all could have been so different for him; just imagine the impact that Klopp might have made had the club beaten Tottenham to the punch for this rough diamond eight years ago…