In Brendan Rodgers' final transfer window as Liverpool manager, he unknowingly began laying the foundations for the club's maiden Premier League title triumph.
It's probably what he hoped he was doing, but Rodgers would likely have envisioned himself at the helm instead of some charismatic German fella.
The now Leicester boss signed teenager Joe Gomez from Charlton, and Roberto Firmino from Hoffenheim, and the pair would go onto play pivotal roles in Liverpool's charge towards the 2019/20 Premier League title. He also p*ssed £32.5m away on Christian Benteke...but the less said about that the better.
Arguably Rodgers' finest hour in the 2015 transfer window was persuading James Milner to trade the trophy-laden, bottomless money pit of Manchester City for his Liverpool side who had lost 6-1 to Stoke 11 days earlier.
On 4 June 2015, Milner agreed to take a £15,000 per week pay cut and sacrifice Champions League football in order to move to Anfield.
It was a huge gamble. Rodgers was under substantial pressure after his side had failed to replicate their antics of the previous season. Milner was dropping out of the Champions League - the one trophy that had so far eluded him - and at the age of 29, he may never have got another chance to play in the competition again, let alone win it.
It has since proven a masterstroke for all involved.
Five years on, Milner is a Champions League winner, a Premier League champion elect for the third time in his career and is showing no signs of slowing down at the age of 34.
Just four months after Rodgers' unveiled Milner as his newest Anfield recruit, he had been shown the door. The Northern Irishman was replaced by Jurgen Klopp, who gradually oversaw a huge squad overhaul. Players not up for gegenpressing were politely asked to leave.
In the space of five years, the squad Rodgers left for Klopp has been significantly upgraded. Simon Mignolet, Martin Skrtel and Jordan Ibe were out, Alisson Becker, Virgil van Dijk and Mohamed Salah were in.
Milner, however, has stood the test of time.
He was instantly able to adjust to the demands of Klopp's high intensity pressing, and the Liverpool boss has since taken advantage of his versatility, with Milner popping up at left back, right back and across the midfield while at Anfield.
It is a testament to the former Leeds' man's attitude and professionalism that he continues to be used in Liverpool's midfield three at the age of 34. While the likes of Steven Gerrard and Wayne Rooney have played out the twilight years of their careers in more stationary, deep lying midfield roles, utilising their superb vision and awareness once their pace has deserted them, Milner still has the legs for Klopp's all action, high intensity, high energy midfield.
He is a man who continues to defy age. In December 2019, Milner put pen to paper on a contract extension, keeping him at Anfield until 2022. Liverpool do not tend to offer players in their 30s more than a 12 month deal.
But Milner still has the engine of a man in his 20s, so this club policy was wavered for him.
308 - Jordan Henderson played more Premier League games in this decade than any other player, one ahead of teammate James Milner (307). Leader. #Opta2010s pic.twitter.com/kqzZMRRHY9
— OptaJoe (@OptaJoe) December 30, 2019
This is not just any old team offering Milner an extended stay. This is a world class Liverpool side. They are one of the most complete teams to ever grace the Premier League. They are on course to break a Premier League points haul. James Milner has made 33 appearances in all competitions this season. At the age of 34, he is still as important than ever.
The change that Liverpool have undergone since the arrival of the former England international five years ago is astonishing. Milner is obviously not entirely responsible for the club transitioning into the best side in Europe.
But when he moved to Merseyside, Kolo Toure and Daniel Sturridge were the only other players in the Liverpool dressing room to have won the Premier League title. The attitude and mentality of a real, dogged winner will have rubbed off on the rest of the squad.
Five years on and the standards Milner has set, his maturity and the respect he commands have been so vital in Liverpool's conversion from nearly men to a relentless winning machine.
Source : 90min