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Back in December, Pogba's agent Raiola dropped a huge bombshell on the eve of United's crucial final Champions League group stage game, saying the Frenchman's time at the club was 'over.'
The backlash against the midfielder, and his often controversial agent, was understandably hard by the fans, with United going on to lose their game against RB Leipzig the next day and crashing out of Europe's top club competition.
Since then things have calmed down and Pogba has reached some of his best form since returning to United in 2016 and United as a team are looking better in general too.
There had been talks of a new deal in the summer for the World Cup winner, but now Raiola is at it again, claiming there are doubts about the 28-year-old's future.
"When a player asks you, what are we going to do? - It's an enormous responsibility. That's when you stay up all night thinking about what's best," the Dutchman told AS when asked about Pogba renewing his contract.
"My aim is to make it a process alongside the player to see what they really have in their heart.
"...With Pogba, what's really important too is what Manchester United want, what project they are proposing for Pogba.
"Pogba has always been interested in one thing, winning the Champions League, titles, that's his objective. And we'll see if that's possible at United or at other big European clubs."
The former Juventus midfielder has long been linked with a move to Real Madrid, even when he was still playing in Serie A, and a connection with manager Zinedine Zidane has been part of that.
Asked why the Frenchman isn't already at the Bernabeu, Raiola said, "It's a question for Madrid.
"At one time, Pogba felt a lot of love for, and trust in, United, and there are various other clubs. Afterwards, it's really hard for United and Madrid to reach an understanding on a massive transfer, because big clubs don't like selling great players to other big clubs.
"And I'm not going to kid you, for Pogba, playing at Madrid was always a really attractive option, because of Zidane too. He's Pogba's childhood hero."
On whether that move could still happen, Raiola refused to rule it out and even suggested a swap for former Chelsea forward Hazard, adding, "I don't know. I think nothing is impossible, but football depends on the day. Just like that. And you need to be flexible to think about all the possibilities.
"What if tomorrow Madrid want to do a swap, Hazard for Pogba. It's just an example. And it all four parties like it, why not?"
United fans will undoubtedly hate hearing Raiola bring questions to Pogba's future once again, and it seems like the worst timing once again.