Luke Shaw's time at Manchester United hasn't been the smoothest that the club has seen.
Shaw moved to Old Trafford in 2014 when he was just 19 for £30 million - then the most money ever spent on a teenager.
The then-Southampton left-back had just played for England at the World Cup and looked set to make the position his own for the foreseeable future.
But injuries and fallouts have hampered his progress quite dramatically, limiting him to just 43 Premier League appearances in fours years - 17 less than he'd managed in his two seasons with Southampton.
And now Shaw enters the fifth and final year of his United contract - leaving all parties with decisions to make.
The 23-year-old has reportedly been offered a new deal, something that didn't look likely at the start of the summer.
But a condition of Shaw's has made the process very complicated for everyone.
"I don't think I would want to sign a contract right now because I want to prove to people that I deserve a contract," said Shaw. "I don't want a contract because maybe in the next year or so I'm a free agent, so maybe they might look to tie me down for that.
"I want to sign a contract because I deserve it and the club want me to sign one."
It's a very admirable stance from Shaw - not many players would be so quick to turn down United - and it's totally understandable that he wouldn't want to tie himself down only to see a new player join in his position.
The stance makes things difficult for United, though.
They want to sign him to a new deal and are showing their faith by not signing a new left-back in this window.
Shaw, however, wants to wait until the season is underway to prove himself, meaning United would be left in a situation where they haven't signed a replacement and the player can still leave for free.
It's going to take a lot of faith from someone to fix this one - either Shaw signs and believes no one else is coming to take his place, or United give him time in the belief that he will sign.
There isn't long to go; someone better make a decision.