This special feature looks at the talismanic talent of Jack Grealish, told through the eyes of the managers he's worked with during his career to date.
It took no time for Tim Sherwood to recognise the talent of Jack Grealish.
Sherwood was on Harry Redknapp’s first team coaching staff and whispers were turning into screams when it came to the buzz surrounding the talented starlet who was making his way through the academy system at Bodymoor Heath.
Tottenham’s Under-18s were due to play their Aston Villa counterparts and Sherwood was interested in going along – as long as Grealish was playing.
After putting in a call, he found out the 16-year-old was, indeed, starting and made his way to the Midlands to take in the game.
Sherwood takes up the story.
“I was working with the first team – coaching with the first team – and I took an interest in the younger players. I liked to see special players and there was a lot of noise around Jack Grealish.
“Our youth team played at Bodymoor Heath one morning, I found out Jack was playing, drove up, and he was just turned 16 and playing against our 18s.
“And I stood there and watched him. The game needed a second ball. Like I have always said, the ball is his friend. It was like it that day. He treated it so well and it repaid him.
“He was a baby, really, but he had such audacity. I remember the final whistle blew, he flicked the ball up into his hands and then gave it to the referee.
“I just loved the arrogance – in a good way, in a nice way – and the confidence in him being assured of himself.
“I remember when I got back, Harry said ‘how did we get on?’ I said ‘I don’t know, I didn’t go for that, I went to see Jack Grealish.’
At the time, Villa – and then manager Alex McLeish - were interested in signing Spurs midfielder Jermaine Jenas, a move that eventually came to fruition as a season-long loan in August 2011.
But at the start of negotiations, Sherwood – following his spellbound view of Grealish in action – suggested an audacious, alternative offer be put to the claret and blue outfit.
“I said to Harry ‘listen, I know they want Jermaine Jenas, swap him for this kid.’
“He was like ‘what, he’s only 16, he’s not going to play for me’. But, for the future of the club, I thought it would have been a dream move. JJ ended up going there anyway.
“I just think Tottenham could have done a deal.
“I just think he’s special. The bigger the occasion, the better he becomes. He’s someone I’ve admired for a long time.”
Sherwood saw huge potential in Grealish in those formative years and he actually helped nurture that talent when he walked into the Villa Park hotseat in February 2015.
Grealish had been firmly on the periphery under Paul Lambert as the Villans hovered dangerously close to the drop zone.
Sherwood never forgot the sight of that outrageously talented 16-year-old strutting his stuff on the fields of Bodymoor Heath as he set about saving the season.
Within moments of entering the training ground complex, he was chatting to Grealish to explain his importance in the team’s revival.
“I kept reading really negative things about him saying ‘he can’t do this, he can’t do that, he’ll let you down, he’s a bad boy’. When I first walked through the door at Villa, I said to Jack ‘I’m not interested in any of that, all I’m interested in is you performing’.
“I think in this country, we read too much about what players can’t do, rather than concentrating on their strengths. And Jack’s strengths far outweigh his weaknesses.
“I tried to play him in his best position. I think it’s really important, when you have a special talent, that you let them play where they want to play. I played him tucked in off the left hand side but free to roam wherever he wants because you could link off him.
“We had Christian Benteke up front with Gabby Agbonlahor and sometimes they’d get shielded by two midfield players. But with Jack, you passed it back to front into him because his touch was so good.
“He can take it in a telephone box. He’s got wing mirrors.
“He’d take it up the field and defensively he’d always come back. But he’d come back so he could dribble it further, which he loves to do.
“But he could take so much pressure off the defenders because he would just take you up the field, win you a throw in, win you a foul, win you a corner. And then when he got into the final third he went straight for the heart.
“I used to say to him ‘I want you to give the ball away more than anyone has it’. That was a positive because he then felt ‘I’m not going to play safe’.
“That’s what I didn’t want him to do because I knew he had the ability. I could go on there and play safe. But I wanted someone to showcase their ability.
“And we were lucky we had him. We had a solid base behind him too. We had Fabian Delph, Tom Cleverley and Ashley Westwood in there, you couldn’t pick three better types for that boy – propping him up. You knew what you would get with them, technically gifted and they just kept giving him the ball. Then it was up to Jack to do his stuff and he did!”
Grealish played a huge role in Villa’s revival in that 2014/15 season as they beat the odds to stay up.
They looked dead and buried for long periods but wins, when it mattered, over the likes of West Brom (2-1), Sunderland (4-0), Tottenham (1-0), Everton (3-2) and West Ham (1-0) earned another season in the top-flight.
Grealish played a huge role in that survival campaign – and also the FA Cup semi-final win over Liverpool at Wembley Stadium.
Christian Benteke and Fabian Delph scored the goals in that 2-1 victory, with both goals set up by Grealish.
The victory is still spoken about fondly all these years later at Villa Park and Sherwood was not surprised to see Grealish thrive in that big moment.
“The bigger the occasion, the bigger the performance. He was huge. Some people sink, don’t they? Some swim. He definitely swims.
“It’s just incredible how he sticks his shoulders back, pokes his chest out and says ‘give me the ball’. “He was that kid I remembered watching when he was 16-years-of-age.
“People are obsessed, especially, in this country by what players can’t do. There’s lots that Jack can’t do. But there’s lots that Messi can’t do. There’s lots that Ronaldo can’t do. Let’s focus on what they can do.
“He entertains people. But, importantly, he’s not a show pony. He affects football matches.”
Grealish has been affecting football matches for as long as he’s been playing.
Coming through the ranks at his boyhood club after joining as a six-year-old, he was a star of the academy team under the mentorship of Tony McAndrew.
His team-mate in those formative years, left-back Lewis Kinsella remains close to him even now.
He’s currently a talent scout but looks back with much fondness at his time playing alongside Grealish.
“When I was at Arsenal, I was playing against Villa and they told me ‘you’re playing against Jordan Graham, an England international’ which I knew would be a tough test. I remember playing against him and someone else said to me ‘wait till you see Jack Grealish, he’s better than Jordan’. I thought ‘Jesus, if he’s better than Jordan, he must be some player’. I thought Jordan was outstanding.
“I remember joining Villa and one of the first games we played together, I came on against Bolton in the reserves and Jack was the same player that he is now – playing with so much confidence, a dribbler, and his love for the game stood out.
“There was a lot of hype around him at the time but when you trained with him and played with him and saw him with your own eyes, you believed in the hype as well.
“He’d just have moments of magic and you’d just be thinking ‘wow’. I remember we played a reserve game and our goalkeeper Benji Siegriest volleyed one out and it was heading towards our coach Gordon Cowans and Jack slid, managed to keep the ball up while it was still on the white line and he dribbled off with it. I was like ‘how has he done that.’
“There was so much confidence, so much belief in his own ability and that’s what’s got him to where he is today.”
The proudest moment of Grealish’s time in those youth ranks was, undoubtedly, the club’s victory in the short-lived NextGen Series in 2012/13, scoring in an extra-time semi-final win over Sporting Lisbon before excelling in the 1-0 final victory over Chelsea, held in Lake Como.
Kinsella, who also starred in the tournament victory, remembers the competition fondly.
“The team that Tony [McAndrew] built was full of both hard-working players but also highly gifted players.
“Jack played in front of me. And when he played in front of me, I was always calm because I had to just give him the ball. That was my job in the game – give Jack the ball. Let him do his stuff. He made my game a lot easier.
“He was outstanding against Sporting and then against Chelsea, he did brilliantly against Andreas Christensen, who was one of their standouts.”
As Kinsella explains, Grealish made his life easier on the pitch – but he did the same off the field, too, as a lads holiday abroad showcased.
“One year we went to Zante on a lads holiday. I was ill so I had to cancel. We were 17 at the time. I remember speaking to the boys and being devastated that I couldn’t come. Jack actually lent me the money to pay for my flights and my hotel and I remember getting out there and he paid for everything.
“That’s when he was 17. It shows the character he has. It’s the measure of the man. He looked after me and I’ll never forget that.
“He's down to earth. He’s not big headed at all. He’s just a happy person who enjoys life. It’s hard not to like him. He just loves his life and loves his football.
“He’s definitely an example, I’ve found this, that the higher up in football you go, the better the people are. I remember Joe Cole and Philippe Senderos when I was at Villa. They’d played at the highest level and achieved the most in the game and they were two of the nicest people.
“Jack is like that. He’s still one of the nicest people around. He’s just such a good guy.”
After showcasing his talents in the NextGen series with Villa, Grealish was on the move at the start of the following term for his first taste of senior football.
He joined Notts County with one aim in 2013/14 – help the club stay in League One.
County had begun the season with a series of defeats before Grealish arrived and the shaky start led to the departure of manager Chris Kiwomya and the arrival of Shaun Derry in the Meadow Lane hotseat.
His performances, especially in the team’s six wins in their final nine games, ensured survival for County against the odds.
Working with Grealish was a joy for Derry.
“When I went in for talks on the Tuesday before I took the job, Jim Rodwell, the CEO at the time, he was speaking so highly of Jack and another loanee at the time, Callum McGregor. He said ‘you’re going to love them, they’re a breath of fresh air, they’re throwback footballers.’ That’s exactly what I found.
“I remember the first training session that I took on the Thursday. I put on a passing drill with a bit of possession and then an XI v XI. Jack had absolutely no interest in the passing drill, none whatsoever. He had a little bit more interest in the possession. But when it came to the XI v XI, I’ve never seen talent like it at that age. He came to life.
“As time went on that was the theme really. He just wanted to play.
“I loved him. I loved him. He was a throwback. He reminded me of myself as a young player – bolshy, confident, backed himself but with so much more talent than I ever had.
“What I love is that he could have sat with the experienced pros and held his own and held court and contributed to a conversation, which is hard for a 17-year-old, or he could have been just one of the younger players, as he was. He could sit in any camp and be very, very comfortable.
“We would have got relegated without him. 100 per cent. No doubt in my mind. Without him, we wouldn’t have won those games we needed.
“We wouldn’t have attacked those last nine games in the same way with the confidence we did. “Without him, I don’t think the club would have held the confidence that it did.
“We knew we had a special player on our hands.”
After that survival season, Grealish returned to Villa, of course, before struggling to make a breakthrough under Paul Lambert.
Sherwood’s arrival rejuvenated him and he was an integral part of his survival season of 2014/15. But, Villa were relegated the following term as they went through four managers during the campaign.
Hope was high with new ownership and new management in 2016/17 but Roberto Di Matteo was swiftly replaced by Steve Bruce.
Bruce ‘took a shine’ to Grealish straight away and says it was a ‘privilege to work with him’.
“I was certainly aware of Jack when I took over at Villa. He burst on to the scene in the FA Cup semi-final against Liverpool. He was only 19 at the time.
“I knew he was a very, very naturally blessed footballer. That’s what I inherited.
“But the one thing I enjoyed about Jack was there was always a smile on his face. He enjoyed football. He’s one of those rare ones where he’d happily be playing with his mates in the park. He just loved football.
“I took a shine to him straight away because of the way he was. I loved his attitude. It was a privilege to work with him.”
Bruce led the claret and blues to 13th in their first season in the Championship as a late bid for the play-offs fizzled out.
He was relishing a fresh crack at promotion with the 2017/18 campaign on the horizon – but Grealish sustained a serious kidney injury in a pre-season collision with Watford midfielder Tom Cleverley during a friendly at Villa Park that summer.
He ended up in hospital and missed the first three months of the season.
Looking back now, Bruce thinks that this was a catalyst moment in the career of Grealish.
There were genuine worries for his career in the aftermath of that injury, but when it became apparent he’d recover, he knuckled down to ensure his prodigious potential was fully realised.
“That nasty kidney injury was a turning point in my view. He ended up in hospital for something that looked so innocuous. It ended up being one of those awful injuries.
“He spent weeks in hospital and months on the sidelines.
“He matured overnight when that happened. He went to work in the gym and he came back, after so much fitness work, absolutely firing. I think that time out was the making of him.”
Another pivotal moment in the career of Grealish, according to Bruce, was the arrival of John Terry as captain at the start of that 2017/18 season.
Terry, after a trophy-laden spell at Chelsea, spent his final campaign as a player in claret and blue.
The impact on the dressing room – and Grealish – cannot be underestimated.
“JT set the example, simple as that. That was what the dressing room needed. And, for someone like Jack to look up to, he was a top pro – he typified what you need to do, how you look after yourself, how you go about your work, JT was all of that.
“You can’t get enough good pros. Every dressing room needs a John Terry. At the age of 36 for a year, he was immaculate. You needed someone like John to lead the dressing room.”
Despite Grealish’s absence in those initial moments of the season, Villa eventually made it through to the play-off final to face Fulham for a place in the Premier League.
They lost that crucial game 1-0 – but it wasn’t for the want of trying by Grealish, as Bruce recalled.
“To be fair, we were poor in the first half and Jack single-handedly went about it in the second half.
“Ryan Fredericks should have been sent off. He stamped on Jack about 29 minutes in. It was right in front of the fourth official.
“But it wasn’t given. Then Jack got up and, in the second half, almost single-handedly nearly got us back in the game.
“Unfortunately, we lost it and I was gone five months later.”
With Bruce relieved of his duties in October 2018, three months into the 2018/19 campaign, Villa turned to a fellow fan, like Grealish, to lead the club in Dean Smith.
Smith, the former manager of Brentford, was relishing linking up with Grealish – and had already spotted areas of improvement for the young forward as he strode positively through the doors of Bodymoor Heath.
“I was really excited to be working with him. I’d seen enough of him previously.
“He’d played against us, when I was manager of Brentford, earlier in the season. I thought he was Villa’s best player on the day and I said that to him after the game. He said he didn’t play that well, which was a typical sign of what I was going to get from him. His standards were always very high.
“I suppose – and it’s been well publicised – my only concern was he hadn’t scored yet that season and he’d only had one assist. I felt like he needed to improve that.
“So my first week, I sat down with him and showed him where I think he could improve and where I wanted to him to be receiving the ball and he just took it on.
“He is a football nut. He’s always concerned about getting better – and how he can get better. He wants you to help him and he thrives on that.
“It was for me to work with him on realising how he could make a bigger impact in the game.
“Rather than dropping deep to get the ball, I wanted him higher up receiving the ball because that’s where he can cause the most problems.
“He’s probably one of the most fouled – if not the most fouled – player in the Premier League and a key reason for that is one of his biggest strengths, which is his balance when he’s got the ball. He puts people off balance, then they plant a foot and then normally foul him.
“On the training ground, he was a joy to have. Well, I say a joy because when you refereed small-sided games, let’s say he was a winner in those as well.
“That was hard work for a lot of our coaching staff, especially John Terry because I used to make him referee him some of the games!”
Together, Smith and Grealish – and a strong supporting cast including Tammy Abraham, James Chester, Alan Hutton and John McGinn - set about returning Villa to the top table of English football.
Grealish had been absent with a troublesome shin injury for four months but returned for the 4-0 home win over Derby in March 2019.
That was significant for two reasons – Smith had made him captain and it was the first of ten victories in a row – a club record.
Grealish, everyone agreed, was a colossal talent but there were few who had him down as a potential skipper – but Smith took the inspired decision to give him the armband and the rest is history.
“With the captaincy, something that people don’t look at as much as they should is that they should be one of your best players because they’re likely to be playing every week.
“Jack was one of our best players, in fact our best player and when he was fit, he was playing.
“I just felt he would embrace it as well. It was his club. He grew up as a supporter. He’d been there a long, long time.
“I thought it would help his maturation as well. We had a good enough relationship in those initial six months where he could come and talk to me about anything so I thought giving him the armband, we could help each other.
“As a captain, he was very conscientious and humble off the pitch. The other players loved him. But the majority of it was on the pitch. He led by the way he played.
“I remember that Derby game, his first as captain, we were under a bit of pressure and he wanted to drop deep, get hold of the ball, hold on to it, win a few free-kicks, just take pressure off others.
“But I also think his character – getting around players, geeing them up – probably went unnoticed because people didn’t see that.
“But he had a good relationship with all the players and would talk to them about their game off the pitch as well as on it.
“Obviously Villa have a proud history and now we’re in the record books for that 10 game winning run. He was pivotal in that, that’s for sure.
“And you can see he was itching to get back, he had something to prove and I think he did that from that Derby game until the Play-Off Final.
“He lifted everybody. He became the talisman during that period. He scored in the 4-0 win over Derby and he scored in the 1-0 win at St Andrew’s against Birmingham City in the game after.
“He scored at Rotherham when we were down to 10 men to help us win 2-1. These were big moments.”
Villa went on to achieve promotion as they made it through to the play-off final for the second successive year, only this time they won, defeating Derby 2-1 in the showpiece game at Wembley.
The following campaign, Smith and Grealish – two boyhood claret and blue fans – spearheaded a survival season for the Villans as they finished 17th, with a last day draw at West Ham ensuring safety.
Improvement was pronounced in 2020/21 and their 11th place finish contained a remarkable 7-2 victory over Liverpool, Grealish having a hand in five of the goals, scoring two himself.
That form led to Grealish’s inclusion in Gareth Southgate’s Euro 2020 squad and, eventually, a high-profile move here to City on a six-year contract that will run until 2027.
Smith, Villa’s manager at that moment, was gutted to see Grealish go – but he’s philosophical looking back.
“He wanted to play Champions League. He wanted to be going out and playing for England in European Championships and World Cups. He was in the squad for England but probably wasn’t playing as many games as he would like to.
“But I think playing at that top level, I think he’d just moved quicker than the football club.
“He loved Villa. He still loves Villa. But, for his career, he had to make that move at the time.
“We were all disappointed because of his character and the relationship we all had with him.
“But I think we all understood as well at this time in his career that he had to make that move.
“A football career goes by very quickly so you can never hold anybody back. Obviously, the price had to be right for Aston Villa and Man City had to pay that as well.
“But we couldn’t hold Jack back from where he was going, which was to be one of the top players in the country playing for one of the top clubs in the country if not the world.”
Grealish is now already a Premier League winner and is chasing another medal in that competition as well as honours this season in the FA Cup and Champions League.
But the player himself admits he struggled to adapt at City in those early stages, as he discussed his start to life at the Etihad in the aftermath of our 1-0 Premier League win at Chelsea.
"It’s so much different to what I was used to at Aston Villa.
“Dean Smith would say to me ‘you go and find the weak link in the defence, in the right, in the middle, on the left, or hug the touchline’.
"I’d been at Villa my whole life, and I’d never had to change. I’ve always been used to that. I didn’t realise how hard it is to adapt to another team and another manager.
"When I came here, I’ll be honest, it was so much more difficult than I thought.
“In my head, I was thinking, 'Going to a team sitting at the top of the league, I am going to get so many goals and assists. But it was so much more difficult.
“So many teams tend to sit in against us which obviously wasn’t the case at Villa.
“But I have been here now 18 months. I am still getting used to it. But I am enjoying it honestly. It’s a great group of lads and it’s a pleasure to work under Pep.”
Now, he’s proving to be a key member of Guardiola’s team, with a sense that he’s one of the first names on the team sheet.
Asked about his performances of late, Guardiola was glowing about the Brummie’s impact as he addressed the media ahead of the visit to Tottenham.
“He’s a starter because he’s playing really good.
“I rotate a lot the team, a lot. But, at the same time, I see how they perform every single game.
“Jack is playing really good and his contribution and assists have been clear.”
In that narrow 1-0 defeat to Tottenham in our last game, Grealish was our biggest threat - continually driving at full-back Emerson Royal.
He was also, as is the norm, comfortably the most fouled player on the pitch – and the second foul on the playmaker by Cristian Romero led to the centre-back’s dismissal.
Guardiola, obviously frustrated with the defeat, was complimentary of the performance of Grealish.
“So aggressive, so committed and had the chances for assists.
“A lot of interruptions as well, but his mentality and aggression to do it, it was good.”
Guardiola is clearly happy with Grealish.
But what do all the other key managers in his career think now they’re watching Grealish excelling at the Etihad Stadium.
Derry admits he watches Grealish and feels ‘immense pride’ in where he’s ended up.
“Everyone recognises Jack Grealish now as one of England’s finest players. But I can’t help but think of the relationship we had together and the club had with him as a 17-year-old.
“I see him as a player who loves the game, the same he did at Notts County as a 17-year-old. He smiles, gets on with people and brings joy to the game.
“I can’t help but feel pride for the small part I was able to play in encouraging him in his first parts of playing senior football.
“He’s been influenced by far more well-known, established managers than me. Of course, he’s been on a journey to places that 99.9 per cent of footballers will never go and tread but, taking it back 10 years and being able to extend his loan at Meadow Lane for the second half of the season and the joy he brought that set of supporters at that time, it does give me an immense amount of pride.”
It's a similar feeling for Sherwood, too, who believes he’s now at the perfect club – and working under the perfect manager in Guardiola.
“He’s playing now, within a structure, where he’s staying on the left hand side, staying wide.
“He gets doubled up all the time. He creates a melee and then he releases to players like De Bruyne and Gundogan so they’ve got space to work.
“People think ‘why did they leave De Bruyne and Gundogan with so much space?’ It’s because Jack has created a melee and then released the ball at the right time. He knows what he’s doing.
“I’ve heard pundits saying ‘well, if you’re the most fouled player, you’re not seeing the picture early enough’. It’s absolute nonsense. He knows exactly what he’s doing. The kid has got a Mensa football brain. He takes it on to the pitch.
“He’s just incredibly bright and gifted and he will continue to get better and better under the guidance of the best manager we’ve ever seen.
“He’s now among other world-class players. His talent was alone at Villa. He was the shining light. “Now he’s a part of a jigsaw. He realises that. He knows his role. He appreciates that he’s among better players now and he’s fighting for titles, he’s fighting for the Champions League. He knows that.
“He’s playing a small part rather than the main event part. But who is the main event at City? “Obviously Erling is scoring goals for fun. Kevin has amazing ability. But they are all part of a jigsaw and they have to do what the manager wants. If they don’t, he doesn’t play them.
“And if you don’t play at Manchester City and someone comes in and plays well, the manager sticks by them.
“Who wouldn’t want to work with Pep Guardiola? Every single day in training must be a joy. You’re not only working on the opposition, you’re working on attacking patterns, too which are what every attacking player would want. It must be the best job in the world being an offensive player for Pep. I think Jack appreciates that. I think he will get better and better.”
Bruce admits he still keeps a firm eye on the career of Grealish – and he’s immensely happy to see him excelling now here at Manchester City.
“I am delighted for him. I am watching his career from afar and remember fondly the couple of years I had with him.
“You sit and smile now. He plays at Man City now with that same enthusiasm, that same smile on his face. He still gets kicked every other week and he still gets up. I am delighted to see his progress.”
Smith has been thrilled to see Grealish improve under the guidance of Guardiola – and thinks everyone who knows him would want him to succeed.
“I think he is a player who has improved but he was always going to improve because that’s what he pushes himself to do.
“He’s had a new coach, new ideas and someone as esteemed as Pep will have improved him tactically certainly.
“He’s the most naturally talented player I’ve worked with. If I didn’t say he was the best player I worked with, he wouldn’t talk to me again! But all joking side, I can honestly say yes.
“I’m proud every single time I see him play. Everyone who comes across Jack just wants him to succeed and go and win more trophies. He’s such a likeable person. He’s a real giver. He gives to other people so much. I wish him well.”
It’s not only Grealish’s talent on the pitch that catches attention, it’s also his look.
He was the poster boy at Aston Villa and he’s taken that on at City, with aspiring young kids idolising the wing wonder.
One of those is Jesse Derry, the son of his former manager Shaun, who plays for Crystal Palace’s Under-15s side.
Grealish is his hero, something dad takes a lot of delight in.
“It's great, isn’t it. I look back at the players I loved and you try and emulate them, of course you do. “My son Jesse plays on the left side of midfield, he’s a right footer and he looks at people like Jack as someone he can look up to and try and copy. That’s what 15, 16 years old do.
“He loves it. He’s got his socks around his ankles, he wears the one-inch shin pads, he’s got the hair band and the barnet that goes with it.
“It puts a smile on my face. And for Jack to be someone I managed is brilliant for me because I can tell him a little bit about him.”
Hopefully, as the years flood by, there’ll be stories of success to last a lifetime.
By Paul Brown
Built with Shorthand