Jurgen Klopp may have conquered the world with Liverpool by winning the Champions League and Club World Cup in 2019 and guided them to their first Premier League title a year later. But the elusive Carabao Cup has so far managed to stay out of his clutches.
Those memorable triumphs in two of the most difficult competitions to win unquestionably hold a greater significance over any other trophy out there. But there is a feeling that Klopp can complete his untouchable Anfield legacy by adding a domestic cup to his silverware cabinet.
Sunday's final against Chelsea, where Klopp takes on his compatriot Thomas Tuchel at Wembley, offers the 54-year-old the perfect opportunity to do just that.
His only serious attempt to clinch the League Cup since arriving at the club in October 2015 ended in agony in his first season when Liverpool faced Manchester City at Wembley. The German has since used the competition to hand opportunities to fringe players and academy graduates.
The squad he inherited from Brendan Rodgers was quite simply not equipped to challenge for honours — and so it proved. Injuries had forced Klopp to deploy Lucas Leiva as a centre-back to partner Mamadou Sakho.
In goal, Simon Mignolet had been handed a new five-year deal by Klopp, but the Belgian was inconsistent in between the sticks and was often blamed for casual errors that a top goalkeeper would not make.
Nathaniel Clyne had been plagued by injury in his Liverpool career but the Englishman lined up at right-back, while Albert Moreno, for all of his pace, was arguably better attacking the opposition goal then defending his own.
Facing the luxury of options his managerial counterpart Manuel Pellegrini could count on would make this a very difficult final for Klopp to navigate his side through. Despite that, the Reds dominated possession as they sought to outplay and suffocate Man City.
Mignolet was at fault for the opener when Fernandinho's speculative effort squirmed through his arms and over the goal line, before Philippe Coutinho levelled with seven minutes of normal time to go.
Prior to that final, Liverpool had won all five of their cup final shootouts, but their luck finally ran out at the sixth attempt. Lucas, Coutinho and Adam Lallana were all denied from the spot by City keeper Willy Caballero, allowing Yaya Toure to clinch the winning penalty.
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Klopp was defiant in his post-match interview, insisting they would lick their wounds and "strike back". The unavoidable truth was that the head coach faced a mammoth task in turning this Liverpool side into winners.
"We have felt how it is to lose. It is not the best moment but on Monday morning maybe we can change everything. We will go on and we will get better," he said.
"We have to work really hard, carry on and there is light at the end of the tunnel. This important."
It was the fourth consecutive cup final Klopp had lost, stretching back to his time at Borussia Dortmund. But instead of dwelling on the defeat, it sparked the beginning of a major overhaul on Merseyside that would propel Liverpool back onto the world stage.
Klopp's first job was to clear out the unwanted figures from his squad in the summer of 2016. That included selling Christian Benteke, Jordon Ibe and Joe Allen, funding moves for Sadio Mane, Georginio Wijnaldum and Loris Karius. Immediately, the trio appeared to represent clear upgrades on what Klopp already had in his squad.
But the defensive fire sale was the most important area that he had to address. Sakho was viewed as a defensive liability and left for Crystal Palace, Martin Skrtel was sold to Fenerbahce, Kolo Toure was released and young pair Jon Flanagan and Andre Wisdom were loaned out.
Later, Moreno, Clyne and Lucas would follow them out the Anfield door, allowing Klopp to start again from the ground up and assemble a backline that could carry out his blueprint for high intensity, 'heavy metal' football.
Of course, it would take time to find the right personnel. Joel Matip arrived on a free transfer from Schalke, which looked a shrewd piece of business given his experience in the Bundesliga, and Klopp knew exactly what he was getting in this towering centre-back who was comfortable with the ball at his feet.
Trent Alexander-Arnold's rise from the academy during the 2016-17 season solved the issue of finding a right-back, but few could have predicted just how influential the No.66 would become at such a young age. With over 200 club appearances to his name, Liverpool's assist king is one of the best full-backs around.
Aided by a thorough scouting and recruitment process, Andy Robertson was signed for just £8million from Hull City in 2017. It was a signing that prompted curiosity, mainly because the Scottish left-back had kept a low profile in English football. But his astonishing work rate and creativity from the wide areas are crucial, as reflected by his double assist in the 6-0 win over Leeds on Wednesday.
But the seismic shift came in 2018, when Klopp beat several clubs to the signings of Southampton star Virgil van Dijk and six months later, Alisson Becker from AS Roma. Both transfers remain Liverpool's most expensive in their history at £75m and £67m respectively, but crucially, they were significant in completing his transformation.
Alisson has proved to be worth his weight in gold and won the Golden Glove award in 2018-19 and only injuries have prevented the Brazilian from adding any more to his solitary award. Van Dijk remains an indomitable presence at the back and top of the class in his trade, despite sustaining a serious knee injury in October 2020.
Many would argue the devastating trifecta of Mohamed Salah, Sadio Mane and Roberto Firmino played a more prominent role in Liverpool's success on the domestic and continental stage.
But when Klopp arrived, he already possessed a talented frontline of Firmino, Coutinho and Daniel Sturridge. His side were leaking goals, making crucial errors at the back and looked incapable of challenging Chelsea or Manchester City for the title.
The defensive changes he made in those two years that followed the 2016 final were significant in building a platform to fall back on, which proved pivotal in the 2019-20 title-winning campaign when they conceded only 33 goals in 38 games.
Even now, Klopp speaks in glowing terms about the effect his defenders have had on Liverpool's fortunes — but none more so than Van Dijk.
"Virgil's arrival was obviously a big day in our common history and it is a good example for a winter transfer and how it works," he said back in December, as reported by The Guardian.
He added: "It was a very important day, it changed a lot for us. All of a sudden we could defend in a different way. We could make the pitch smaller for the opponent, so that was pretty helpful."
Unlike on that day six years ago, Klopp will feel comfortable in the options at his disposal. In Alexander-Arnold and Robertson, he holds a clear advantage over Tuchel's current wing-back options of Marcos Alonso and Cesar Azpilicueta. Van Dijk and Matip will feel confident about keeping an out-of-sorts Romelu Lukaku quiet, while Alisson has kept seven clean sheets in his last nine appearances.
The fantastic five are likely to be present on the teamsheet when Klopp names his starting XI tomorrow.
And with it, he now has the recipe to end Liverpool's decade-long run without a domestic cup success at Wembley, which would truly put those painful Wembley memories out to pasture for good.