It was this week in particular as he is in line for his first return to Aston Villa tonight since leaving his boyhood club for £100million in the summer.
There was a sense of inevitability than when Grealish went from being the main character at Villa to one of a large supporting cast at City it would look and feel different.
He's front and back page news. His calves even have their own calendar.
But in almost every category on the pitch, where he should be judged, his output has dramatically dropped off; he's drawing less fouls per 90 minutes, taking fewer shots, completing less dribbles, creating fewer chances, and his goal involvements average is half of what it was in his final season up the M6 at Villa Park.
Everything that made Grealish one of the most exciting players in the country for Villa and England has been stripped right back in his game.
Jack Grealish has opened up on his 'difficult' adaptation since joining Man City for £100million
Playing for Pep Guardiola is not easy but Grealish has not been the player he was at Aston Villa
'I've found it a lot more difficult than I thought I would, adapting to a different manager and team-mates,' Grealish told the Telegraph.
'At first I thought I'd have more of the ball, get more assists and goals but it doesn't work like that at all. I've had nowhere near as much of the ball as I used to get at Villa.
'I wouldn't say I've struggled, but I found it hard to get used to at the start. I've not had the assists and goals I got last season, but I'm never one to doubt myself.'
To the Villa fans that were left furious at his decision to leave, something he felt he had to do to test himself in the Champions League, there will likely be a sense of smugness that the grass has not proven greener so far in east Manchester.
Injuries hampered his last season at Villa but he still rounded out the campaign with 12 assists and six goals. Whenever he stepped out of the side they appeared to be void of ideas.
Joining City for £100m, he finds himself under the microscope for his displays every week
In almost every per 90 minute average he has dipped since his final season at Aston Villa
Yet at City he is not the sun to which the earth orbits. He is one of many complimentary pieces that are being coached relentlessly to play football the way Guardiola wants it to be played - and the Catalan has no appetite to give his big-money signing a free pass.
'I'm not thinking, "The best Jack Grealish we are going to see is next season". I want to see it this season,' Guardiola said recently, laying down the gauntlet.
It would be