Paul Pogba's return to Manchester United was supposed to herald the start of a new era at Old Trafford, but just over five years on it's in danger of ending the same way it did when he first left in 2012. The France midfielder is still the most expensive signing in the club's history at £89.3 million, and he is seven months from leaving as a free agent for a second time.

It wasn't meant to be like this.

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Executive vice-chairman Ed Woodward was so pleased at securing Pogba from Juventus in 2016 in face of fierce interest from Spanish giants Real Madrid that he told colleagues it felt like a "watershed moment." United could do nothing to stop Cristiano Ronaldo leaving for the Bernabeu in 2009, and for Woodward, the arrival of Pogba signalled a turning of the tide, giving notice to their peers and rivals that they were back as one of European football's major players. But it didn't trigger the wave of success he was hoping for, and there have been as many controversial moments as goals, assists and trophies.

On Monday, Pogba picked up a thigh injury during a shooting drill with the France national team, and having been initially ruled out for around two months, by the time he returns he'll be eligible to begin negotiations over a precontract agreement with clubs outside the Premier League ahead of a possible free transfer on July 1. It was the same in 2012 when Pogba, then 19, left to join Juventus; how it will end this time is still up in the air, and the way it is likely to play out from here depends on who you talk to.

Sources have told ESPN that United chiefs are losing hope of extending Pogba's contract. Meanwhile, Pogba's representatives, headed by agent Mino Raiola, have not ruled out staying and say they are "calm" about the situation.

United believe their financial stability through the coronavirus pandemic could yet play into their hands because of doubts over whether Real Madrid, Barcelona, Juventus or even Paris Saint-Germain can afford the type of wages Pogba would want. Raiola, though, insists that Pogba's next move will be determined by where he's most likely to win things. The truth is probably somewhere in the middle.

Pogba has won the Carabao Cup and the Europa League in four-and-a-half years at United, but hasn't been close to a Premier League or Champions League title. For context, had he chosen Real Madrid in 2016, he would have won La Liga twice and back-to-back Champions League titles in 2017 and 2018.

Pogba and Raiola have, of course, been keen to play down the monetary aspect -- at least in public -- but there's no escaping the fact that, at 28, this will be his last big contract. A five-year deal, for example, would take him to the summer of 2027, when he will be 34.

Failing to keep Pogba at the club would be a huge personal disappointment for Woodward in particular. He still describes it as the most difficult deal he's been involved in, with parts of the agreement so complicated he had to lean on knowledge he acquired as a tax adviser in the 1990s.

Upon taking the top job at Old Trafford in 2013, Woodward made it his mission to meet Raiola in the hope that their relationship would pay off down the line. It helped get Pogba back to United, but it has not yet been enough to keep him there.

The club have been frustrated at Raiola's repeated public declarations that the midfielder is unhappy. In December 2020, on the day of a decisive Champions League group game against RB Leipzig, he said: "It's over between Manchester United and Pogba." Manager Ole Gunnar Solskjaer was initially furious at the timing of the comments, but later accepted Pogba's explanation that the interview had been done more than a week earlier.

Solskjaer has been praised for his man management, but sources have told ESPN other teammates have been left frustrated at what they believe is preferential treatment. Jose Mourinho complained during his time in charge that he had tried to motivate Pogba with both praise and criticism in public but that nothing had seemed to work. By the end of Mourinho's reign, his relationship with Pogba had completely broken down, but Solskjaer has gone out of his way to keep the player happy and engaged.

That effort has not always been repaid; in Pogba's past two appearances, he has been sent off after 15 minutes against Liverpool and substituted early against Atalanta after a dire performance. In contrast, Pogba's season started with seven assists in his first four league games.

"Brilliant one minute, liability the next" has been the story of his second spell at United. If this is the beginning of the end (again), it would be hard to argue that United have had the best of their most expensive signing. Until this saga is resolved, the next era of success at Old Trafford is still on hold.