Flitcroft was the coach under manager Keith Hill, who helped the 23-year-old midfield maestro chalk up 100 appearances for Barnsley before he earned a move to the Premier League with Norwich City.
The Bradford-born playmaker was “the best player in the Championship” during his Oakwell days, according to Flitcroft, and the Reds manager admits he was thwarted several times in a bid to bring Butterfield back to South Yorkshire.
After struggling in Norfolk, resulting in loans spells at Bolton and Crystal Palace, Butterfield joined Tony Mowbray at Middlesbrough in the summer and will look to increase the pressure on Flitcroft and his bottom-of-the-table Reds this afternoon.
“At the time, when he hit his form, I believed he was the best player in the Championship,” said Flitcroft. “I think he can get back to that level again.
“We tried to bring him back a few times, three or four times, but the manager down at Norwich didn’t feel it was right to bring him back to his old club. I did.
“There’s been a couple of times we have hit the bar, but he wanted to be a part of the Crystal Palace project.
“His attitude and talent is incredible and a player you would want to work with again.”
At 21, Butterfield was Barnsley’s youngest captain of all time and it was that decision by Hill to give the midfielder the captain’s armband which helped him transform his career.
“We saw in Butts from day one his qualities,” said Flitcroft. “But we saw the other side that he didn’t want to do.
“Hill making him captain, leading by performance, gave him the responsibility that no one (had) ever trusted him with.
“We worked hard on his fitness, he got his body in great shape, and I have not seen many players worldwide who can take a corner with his left foot and right foot.
“When we saw him in training, we knew we had a special talent.
“The Norwich adventure, he just didn’t make the games and I was worried about him becoming a football ghost.
“You can look at Butts sometimes and think, ‘does he really love football?’ But when you get to know him, he loves football as much as any player I have ever met. He is obsessed to playing football matches, his drug, the thing that buzzes him up.”
Butterfield, who started out as a youngster at Manchester United before being picked up by Barnsley in 2007, has impressed in his short time on Teesside and is looking forward to seeing some familiar faces today.
“Obviously, playing against my old team provides extra reason for me to put in a good performance,” he said. “I’m looking forward to seeing some old faces again. They showed me the right path at the start of my professional career.
“I feel like this time I’m back in a position where I’m full of confidence and can play really well.
“But I know the manager and a lot of the Barnsley players – it’s going to be a really tough game.”
Mowbray, who said Boro tried to sign Butterfield from Barnsley, said: “His performances are steadily growing, he’s becoming more confident around the building and in the role we’re asking him to do.
“He knows more about the players around him and the shape we’re playing and his role in the team now. He’s getting stronger and better and capped a great performance in the last game with a strike from 25 yards that will give him great confidence.”
Barnsley may sit bottom of the Championship, but Flitcroft has been impressed with his squad’s fighting spirit.
Striker Marcus Pedersen and winger Paddy McCourt both rejected international call-ups in favour of staying at Oakwell this past fortnight to prepare for today’s game.
“Marcus has had an excellent week’s training,” said Flitcroft. “He was asked to go on international duty, be part of the squad, but wanted to stay and really get himself up to Championship speed.
“The commitment’s there from Pedersen, and it is the same with Paddy McCourt. He got a late call and was asked to go on international duty, but didn’t want to because he wanted to be part of what we are doing here.
“These lads are fighting and scrapping to be part of this squad, to get that forward momentum. As a manager, it delights you going into work, knowing you have players like that.”
The job now for Flitcroft is to gel last season’s battlers, who avoided relegation against the odds, with quality signings like goalkeeper Jack Butland, Pedersen, McCourt and midfielder David Fox. “We have had a really good two weeks,” he said. “It’s galvanised the squad, and we’ve worked on things which, during a Saturday-Tuesday game week we weren’t able to do.
“It’s been good to have that condensed time with the squad.
“We know where we are, we are at the bottom of the league, and the only way we can go is upwards.
“There has been a transition in the squad, I do feel that. For a squad that achieved so much last season, a real tight group, it’s been difficult adding players to that as they haven’t had the experience of last season.
“With the reinforcements brought in, you can see there has been a shift in the dressing room. That’s something we are managing on a daily basis and is something that excites me because we want to take the team in a direction this season.”
Boro youngster Ben Gibson will today face a physical battle against Chris O’Grady, with either Jason Scotland or Pedersen partnering him up front.
Manager Mowbray is keen to see how the 20-year-old rookie stands up to the challenge, with experienced centre-backs Seb Hines and Jonathan Woodgate close to full fitness.
“He’s done well and playing against two big powerful boys in Chris O’Grady and Jason Scotland will be a test of how far he’s come,” said Mowbray.
“These last three games his performance level has been fantastic – I’ve been especially impressed by his concentration.
“Of course, there are big challenges ahead for him but the Barnsley front two might think ‘right, we bully this young kid’ and try to physically ask questions of him.
“Seb Hines and Jonny Woodgate are getting much closer to being fit and, hopefully, if Ben can keep playing as he has been then we might not need to bring anyone in.”