Richard Hughes took on the seemingly impossible job when agreeing to become Liverpool sporting director in March last year.
This summer the Scot has broken the British transfer record by signing Alexander Isak, while overseeing the biggest transfer spend in the club's history.
This is how he did it.
After Michael Edwards agreed to return to Liverpool under a new, expanded brief of chief executive of football for Fenway Sports Group [FSG] in March 2024, the very first thing he did was pick up the phone to Hughes, on gardening leave at the time having just decided to quit as Bournemouth's technical director.
The duo's close relationship dates back some 20 years to when Hughes was a hard-working midfielder and captain of Harry Redknapp's exciting Portsmouth side and Edwards a performance analyst on the south coast, with the two, both deep thinkers, striking up an immediate bond over analysing the game.
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Not officially due to start his role until June 2024, and with a to-do list that not only included negotiating new contracts for three of Liverpool's biggest stars - Trent Alexander-Arnold, Virgil van Dijk and Mohamed Salah - but also somehow finding a successor to Jurgen Klopp, the new man appeared to have been handed a hospital pass.
The latter was the more urgent priority given Klopp's near decade-long stay at Anfield was coming to an end, although Liverpool had already been dealt a blow with the news Xabi Alonso - their former midfielder who had been heavily tipped to replace the German - would be staying as Bayer Leverkusen manager.
Ruben Amorim, one of Europe's most sought-after young coaches having guided Sporting Lisbon to the brink of a second Portuguese title, was now reportedly the front runner for the role, but Hughes had other ideas.
Having poured over the data supplied to him by the club's director of research, Will Spearman, Hughes knew there was only one candidate he wanted to speak to and in April flew to the Netherlands to meet Feyenoord head coach Arne Slot at his home in Zwolle.
The Dutchman had scored highly when it came to both improving players and keeping them fit, while importantly unlike with Amorim, he played the same formation and style of football as Klopp.
Slot has recounted how Hughes came to that first meeting armed with huge folders of detailed information on him and his team, joking the Scot knew stuff about him even he did not.
"Liverpool were so clear they wanted to have me, and they knew everything about me," he said. "Immediately it was: 'OK.' Richard knew many, many, many games and many of the assessments I've made during games - the changes I made in tactics. Julian [Ward, FSG's technical director] visited the [Feyenoord] training ground and spoke with a lot of people trying to get some knowledge for the club and how I worked. There was not a stone unturned."
To the outside world, Slot's appointment was viewed as a risk given he had relatively little Champions League experience and only won two major trophies in Holland. Hughes, though, backed his judgement, just as he did when taking the unpopular decision not to stick with his friend Gary O'Neil as Bournemouth manager in the summer of 2023, but to go with the relatively unknown Basque Andoni Iraola.
Both would turn out to be shrewd appointments. However, with Liverpool's underwhelming summer 2024 transfer window seeing the arrival of only two players, one of whom in Giorgi Mamardashvili immediately loaned out and the other in Federico Chiesa arriving under an injury cloud, the pressure from outside was already mounting.
Hughes' early standing with the club's supporters was not helped either by his failure to get the £51m Martin Zubimendi deal over the line after flying to Spain in August having been assured by the holding midfielder he wanted to move to Anfield, only for a late change of heart from the Spain international.
However, while many Reds supporters fumed over the club's lack of transfer activity, Hughes stayed cool in the knowledge Slot's training-ground coaching - including the pivotal decision to drop Ryan Gravenberch back as a No 6 - would improve a squad which had led the Premier League table at the start of that April.
And so the duo agreed to play the 2024-25 season with Klopp's squad, allowing Slot to make judgement calls on players at the end of that campaign.
"Jurgen left the team in a good place and we are trying to build from there," said Slot on the eve of the season. "We're not changing everything. Actually, we [didn't] change that much because many things were already good."
Either way, all eyes were on Hughes in the opening weeks of the campaign to see how the team would perform without Klopp on the touchline, but despite Slot making a record-breaking start to life as Liverpool head coach, the Scot now needed to secure the futures of the club's 'big three'.
Van Dijk, Salah and Alexander-Arnold's contracts all expired the following summer, meaning all three could start negotiating with foreign clubs as early as January 2025.
Hughes confided he was hopeful of keeping one of the trio, but as the season progressed, even that prospect looked bleak with Alexander-Arnold and Van Dijk's camps both silent, unlike Salah, who revealed "no one" from Liverpool had talked to him and it would "probably" be his last season at the club in an on-pitch interview with Sky after a 3-0 win at Old Trafford in September.
The Egypt forward, in the midst of his best-ever season at Anfield, kept the heat on Hughes by revealing he had still to be offered a new deal and was "probably more out than in" after his double helped keep the Reds top of the Premier League with a comeback win at Southampton last November.
The Glaswegian has a reputation as a "fierce negotiator" who is ice-cool even in the most pressurised situations, described by one agent as a "robot", while his detailed knowledge of the game is a huge asset when it comes to getting a deal over the line.
Hughes speaks four languages after growing up in Milan, where his father Kevin worked for Penguin Books and would take a young Richard, by then picked up by Atalanta's famed Academy, to San Siro to watch Arrigo Sacchi's great AC Milan side of the late eighties and early nineties.
These skills and knowledge would come in handy as Hughes continued to seek a breakthrough in negotiations with the trio's agents, including Ramy Abbas, the tough Colombia-born lawyer who represented Salah.
Van Dijk and soon-to-be crowned double Footballer of the Year Salah eventually agreed new two-year deals in April as the Reds closed in on the title and although Hughes was unable to persuade Alexander-Arnold to extend his stay with his boyhood club, keeping two out of three still represented a fine achievement from the Scot.
Hughes barely had time to sit back and bask in the glow of Liverpool's record-equalling 20th top-flight title, masterminded by the coach he had brought to Anfield, before unusually for a team that has just been crowned champions, embarking on a major summer rebuild spearheaded by Florian Wirtz's arrival from Bayer Leverkusen.
The best young player in Germany was expected to join either Bayern Munich or Man City, only for Hughes, along with Slot and Edwards, to convince the 22-year-old his future instead lay at Anfield with another in-depth pitch to him and his parents.
"It was not easy for me to decide, but I think the talks with the coach and Richard and everybody were, from the start or from the very first time, so good and it just kept going like this," Wirtz said of his decision to join Liverpool in a then British-record £116m move in May.
"Every time I spoke to one of the [people from] the club I felt like, 'this is the place I want to be' and so in the end I was really 100 per cent convinced I want to join Liverpool and it was the best choice."
Wirtz's shock arrival bore all hallmarks of the sort of audacious transfers Edwards used to regularly pull off during his time as Hughes' predecessor, such as Van Dijk's arrival for a word-record fee for a defender before the 2018 January window had even opened.
However, the data from Spearman and his team told Hughes this was a generational talent Liverpool could simply not pass up on if the opportunity arose, despite the eye-watering numbers involved, as was also the case with Alexander Isak's stunning move from Newcastle United.
Slot's side scored a league-high 86 goals en route to last season's Premier League, before signing France striker Hugo Ekitike in July for £79m to replace the departing Darwin Nunez in a move Hughes laid the groundwork for the previous summer, leading some to question why the Reds needed another No 9.
According to their statistical models, though, the Swede ranked alongside only Kylian Mbappe and Erling Haaland when it came to Europe's top marksmen, resulting in a summer-long transfer pursuit made more spicy by the fact Newcastle manager Eddie Howe is one of Hughes' closest friends from their playing days at Fratton Park and then Bournemouth.
Business is business, however, with Hughes putting aside a two-decades long association to get a British-record transfer over the line, even after the window had officially shut on Transfer Deadline Day.
That £125m Isak deal took the champions' spending this window to a record £446m, also easily surpassing their own previous highest total of £177m under Edwards after Klopp's side had just won the Champions League in the summer of 2019.
Hughes, though, has also managed to bring in an eye-catching £218.4m from player sales this summer - on top of the £62.5m he generated in his first-ever window in charge - meaning incredibly, the Reds' net spend [£218.4m] was actually less than Arsenal's [£257m].
For Hughes, it has been pretty much non stop since taking up the role, barely having time to holiday with his wife and five kids in Crete, before working till the conclusion of Deadline Day to get the Marc Guehi move finalised, only to miss out on the defender when Crystal Palace pulled the plug late on.
Meanwhile, in recent days Hughes also had to negotiate James McConnell's new deal and loan to Ajax, as well as a contract extension for Cody Gakpo, and he must now turn his attention to persuading Ibrahima Konate to commit his long-term future to the club.
But that can all wait as the Liverpool sporting director enjoys a well-earned international break, before no doubt trying to resurrect the Guehi deal when the window re-opens in January.
