Sherwood's mixed emotions towards the 19-year-old academy product stem from the fact that he has been making back-page and front-page headlines in recent months.
Grealish shone at Wembley in April as he helped Villa defeat Liverpool to reach their first FA Cup final in 15 years
But just a few days afterwards he was photographed inhaling the popular legal high nitrous oxide on a night out.
He was on the wrong side of his manager again during the summer when more pictures emerged of him face down in the street while on holiday in Tenerife.
Grealish is in contention to make his first appearance of the season against Crystal Palace at Selhurst Park on Saturday after missing the start of the campaign with a hamstring injury.
And Sherwood insists he will welcome the youngster back with open arms because he is a rare talent
"I will back him 100 per cent, he is such a talented boy," said Sherwood
"I love him to death and I hate him at the same time! I want to nurture him to fulfil his full potential.
"He did annoy me in the summer, but he annoyed himself
Hopefully the penny has dropped with him.
"Young kids make mistakes
But they come through it
He is a one-off - and he is a one-off on the pitch
He has come through it and we need to move on now."
Grealish made a goalscoring return from his injury for the under-21 team this week and is likely to go straight into the starting line-up against Palace
Carles Gil also played in that game against Derby on Monday and he too comes into the reckoning after an ankle problem
Villa have beaten Bournemouth and lost to Manchester United so far this season in the Barclays Premier League and Sherwood believes the return of Grealish and Gil could provide the creative spark that has been missing
"That is what we need, we need Jack and Carles," said Sherwood
"It is unfortunate that two of the most creative players in the side have been injured at the same time
Now they are getting back to fitness, it will change us going forward
"I think they could play together
If anyone watched them play for the under-21s, you can see they suit each other's game
They pass the ball to each other and they enjoy each other's company
"They are very offensive players with a good technical ability so they can take us forward."
Sherwood admits his young side will face a tough test at Selhurst Park against a vastly more experienced Palace team
He said: "They have got some very good players and Alan (Pardew) is a very good manager
"They are a side full of men
"They have pace on the counter-attack and we have to be ready for that
They bring teams on to them and spring on you with the pace of Zaha, Bolasie, Puncheon
"But we have to be ready for that and I want to show far more attacking threat than we did against Manchester United."
Although Grealish and Gil return to the reckoning, Jores Okore remains out with a knee injury and Jose Angel Crespo is still working his way back from a groin problem
New winger Adama Traore, who arrived last week in a £7million deal from Barcelona, could be included in the travelling party
Source : PA
Source: PA