Blades tattoos, Jamie Vardy and Ian Holloway's wife: The inside story of Lee Gregory's journey to Sheffield Wednesday

Sat back on her sofa one evening, Kim Holloway allowed her eyes to drift to the television and focus on the football being shown on it.

Sunday, 17th October 2021, 5:00 pm

The wife of borderline national treasure Ian Holloway, she watched for a moment or two and then went back to what she was doing.

Breaking the silence an evening in front of a television often involves for a married couple, she lovingly mumbled a few words that would change the life of a young footballer from Batemoor forever; “You used to sign players like that.”

It was 2014 and Lee Gregory was charging about as the front man at FC Halifax Town at the time, a part-time West Yorkshire club who three years earlier had attracted headlines by selling a certain Jamie Vardy to Fleetwood Town for a record non-league fee.

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Mrs Holloway’s words planted something of a seed in the mind of her husband, then Millwall boss. A period of scouting and research followed and 11 years on from his release from Sheffield United as a skinny teenage defender, Gregory was soon back in the Football League.

It’s a big break story scarcely believable and as time has moved on has been put down as one of the myths these rags-to-riches football tales can often see embellished and spat out as something more fantastical than the reality.

But every word is true and confirmed by Scott Cropper, a Sheffield Wednesday season ticket holder who has known Gregory since he was old enough to kick a ball through a pair of jumpers.

“He’s always been a pretty steady lad,” Cropper said, barely believing his oldest mate now leads the line for the club he’s always supported. “He was always pretty quiet growing up and came out of his shell in his late teens.

Sheffield Wednesday number nine Lee Gregory has risen up through the ranks since his release by Sheffield United as a teenager.

“Through school you could see he had something about him, there are good players but Lee always had something different you couldn’t necessarily put your finger on. When he was released by United he was playing as a right-back. They told him he was too small.

“But even then, when he had to start at the bottom and work his way up, he had something about him where he knew he was going to make it. When we used to go out round town and stuff, he would drive us. He didn’t want to drink because he had this determination to do something.”

To look at Lee Gregory now you wouldn’t think a club could have used the excuse that he was too small as a reason to release him. In the weeks after that bombshell he started going to the gym and developed the strong, rough and tumble style of play Wednesday have seen the benefit of this season.

He worked as an electrician throughout his time in non-league and like any other lad his age could often be found playing in five-a-side leagues on spare evenings. It goes without saying that when he was available, his team seldom lost.

Bulked-up, he was shunted up front to play as an old-fashioned number nine at Sheffield FC before a spells Staveley Miners Welfare and Mansfield Town who – then in the Conference – also decided they didn’t quite fancy him.

It was in the shadows of Halifax mills – first on loan and then on a permanent basis in 2010 – that he found sanctuary and a strike partner in Vardy that got things going. Though the pair didn’t play together long before the now-Leicester City man moved on, they remain good friends.

Halifax were on their journey back from liquidation back then but their partnership fired the Shaymen to promotion from the Northern Premier League at the first time of asking. After Vardy’s departure, Gregory took centre stage and inspired promotion to the National League after just two seasons. He scored 82 goals in 129 league games for the club.

“Obviously Millwall was his big break,” Cropper said, “but it was Halifax that made him. They were the ones that gave him a chance and he repaid that. They sort of grew together and I know he looks back really fondly of his time there.

“A few of us used to go up to watch him every now and then and you could see he was miles better than the defenders he was playing against. It all seemed to click for him from there, really.”

Enter Kim Holloway, enter Millwall and Stoke. Enter Sheffield Wednesday. The rest, as they say, is history and Owls fans hope the 33-year-old can inspire a new promotion campaign.

The elephant in the room immediate after his signing, of course, was painted red and white.

It was never any secret that Gregory is a Blade from a Blade household. But he was never a match-goer and football for him was always played rather than watched. Daydreams of scoring at Bramall Lane would have only been fleeting.

But what of that Blades tattoo supporters of the other lot swore blind was real in the weeks after his signing with Wednesday?

“I can reassure everybody he does not have a Blades tattoo,” Cropper laughed. “He’s from a Blades family, that’s no secret, but he was never that into it.

“I read the other day that he used to go to all the away games. How could he? He’s played football every Saturday since he was 17. Even if I didn’t know him, it doesn’t add up, does it?

“He’s not a massive Blade. You wouldn’t get a massive Blade playing for Wednesday; Billy Sharp wouldn’t sign for Wednesday, would he?

“I can count on one hand the number of times he’s been to Bramall Lane. There’s no worries there!”

Any fears allayed, then. It’s been a long road to professional football for Batemoor-born Lee Gregory. And he’s loving every minute.