Enniskillen, County Fermanagh, 40 miles from the Atlantic Ocean. On Church Street, they have been serving beer in Blakes of the Hollow since 1887 and a dark atrium upstairs in the old, atmospheric bar seemed a suitable place for Gerry ‘Wee Scone’ Connolly to nudge a document across a heavy wooden table.
Here it was, dated July 2002, the contract from Tottenham Hotspur that took 16-year-old Kieran McKenna from his local club, Enniskillen Town United, to White Hart Lane. The fee stated was £5,000 with “(five thousand pounds)” in brackets for clarity.
There were sub-clauses — another £5,000 ($6,500 at today’s rates) when McKenna signed his first professional contract and a further £10,000 when he made his first-team debut. There was an additional £10,000 clause relating to an international debut — “for either Northern Ireland, Republic of Ireland or England”. It had the potential to be a £30,000 transfer for a teenager 22 years ago.
Connolly intervenes to explain: “The international part of the contract had to be re-written because the reference was to a cap for Northern Ireland. We had to change that when I told them Kieran was born in London — so he was eligible to play for England. And for the Republic, because his mother’s from Monaghan.”
McKenna never did make that first-team debut for Spurs or at senior international level, but he came agonisingly close. Forced to retire from playing at 22 due to a hip problem that would not heal, he channelled his football intuition, intelligence and ambition into coaching.
Kieran McKenna was a coach under a host of managers, including Jose Mourinho, during his time at Manchester United (Martin Rickett/PA Images via Getty Images)
The results at Ipswich Town have been spectacular, taking a team from League One to the Premier League in 30 months. Simultaneously McKenna’s reputation has soared, meaning there was a week at the end of May when it appeared he was about to be appointed by Manchester United, Chelsea or Brighton & Hove Albion.
That each scenario was considered plausible is a measure of the esteem in which McKenna is now held. Ultimately, he signed a new, extended contract with Ipswich that ties him to Portman Road until 2028.
At his first club in Enniskillen, they will be happy with that. Blue Ipswich jerseys have begun to appear among the boys making their way to midweek training (worn by McKenna’s nephews) and during a walk around McKenna’s Irish roots — and his Tottenham route — you discover a serious level of local pride in the 38-year-old.
As Connolly says: “Everybody would love a bit of Kieran.”
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Connolly reckons he first saw McKenna kick a ball when Kieran was around five. The exact date escapes Connolly, but then he has been with Enniskillen Town United since 1970.
The McKenna family had returned from London in the 1980s and Kieran knocked about Enniskillen with two lads in particular — older brother James and a friend, Michael. The Michael in question is Michael McGovern, who won 32 caps for Northern Ireland — McGovern only retired from playing earlier this month having turned 40.
Connolly slides another document across, this time a photograph of all three celebrating together after winning a local junior cup final against Ballinamallard United. “James scored the winner,” he says. James then went on to play for Ballinamallard in Northern Ireland’s top flight.
Kieran was young for such company but that was an indication of his ability — “exceptional”, according to Connolly. Had things been different, McKenna’s talent might have taken him to Celtic.
On a coaching day the Glasgow club held at Derry City, 90 minutes north of Enniskillen, Connolly says, “Kieran was by far the best player on show.
“But Celtic didn’t want to know. Celtic had their mind made up about a boy more, shall we say, well-built. We badgered them after that, so much so that Celtic were to play in a tournament in Galway over Easter in 2001. Foot-and-mouth disease broke out and it was cancelled but Kieran was going to that as part of an Irish-based Celtic team. I often slagged the Celtic co-ordinator that they had two chances to sign Kieran.”
Even at 20, McKenna was listed by Tottenham as weighing 10st 7lb (66.7kg) and his physique was clearly not an issue for them or Enniskillen Town — at 14, there were times when he would play men’s football for the club’s third adult team. Connolly would have liked that to continue. “I’d rather he stayed,” he says. “Because playing against men, you develop quicker. But at 14, he wanted to go and play with boys his own age and that was at Ballinamallard.
“He played up front for us, and he was an exceptional footballer. It wasn’t so much his ability, it was his attitude. You need the ability of course, but there’s plenty who have it but don’t have the attitude. As Kieran got older, he developed more quickly and he was always going to get noticed. The phone calls started coming and I rang Kieran’s mother. She said to give them her number. There were probably a dozen scouts calling.”
At nearby Ballinamallard United, ‘Whitey’ Anderson was in charge. He had been at the club since the 1980s and set up a youth programme in 1996.
“You need to know the geography a wee bit,” Anderson says. “Down in Fermanagh, we felt we needed to offer the players something stronger in the winter — there was no winter league. We contacted Gerry McKee (who will play a part later in this story) to go and play in the Mid-Ulster Youth League.
“Kieran was basically an Enniskillen Town youth player, but in those days you could play for two clubs — one in the winter, one in the summer. I was an IFA (Irish Football Association) county coach and I knew Kieran was an exceptional player. So Kieran guested for us for two years in the Mid-Ulster Youth League.
“He was a central midfielder for us, right-footed, covered the ground well, read the game well. He had a great temperament, which you can see today when you hear him being interviewed. He was also a great team player, always encouraging those around him. He never got into bother with referees.
“Locally he stood out and he was one of those kids who would ask questions — ‘Why are we doing this?’. He was inquisitive, and that is rare — sometimes you wonder if kids are even listening to you. If you’re asking me what’s his biggest attribute, it’s that attitude. He had a desire to succeed.”
McKenna was selected for a representative team to face South Belfast. It was at the Ulidia playing fields — where Irish international matches were first hosted in 1883 — and, as previously mentioned, Gerry McKee was there.
McKee wore different football hats — an IFA coach and administrator, he was also Tottenham’s scout in Northern Ireland. On top of that, McKee is a Spurs fanatic.
“I’d seen Kieran in a few games, and I’d seen he had ability,” McKee says, “then we had a representative game at Ulidia. Kieran played, and he played a ball he says he doesn’t remember, but which has always stuck in my mind. It would have been reminiscent of Glenn Hoddle.
“Kieran was 14. I just turned and immediately went to Whitey Anderson and said, ‘We have got to do something with this kid’. That was it.”
Immediacy in scouting is important — Leeds United and Leicester City were also monitoring McKenna.
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“I sent a report to Tottenham,” McKee says. “The head of the academy was Peter Suddaby and the head of recruitment was John Moncur. I said what I thought about Kieran, his qualities. I didn’t know what they had in the academy midfield but we sent him over and he did well in the trials.
“He flew over on his own to Stansted. This was for a weekend trial. I’ve said before to people in the academy that when our boys go over, they probably don’t sleep the night before the game, so they maybe don’t show their best, it maybe takes a couple of trips. But they saw enough to offer Kieran another trial. John and Peter were very understanding about the development potential of players, especially from here. I left their office and rang Kieran’s mother and that’s when the excitement kicked in. They were going to offer a contract. Kieran was 16. John Moncur came over to Enniskillen to seal it all. Tottenham’s education officer came over as well. All was put in place.
“Kieran stayed with relatives in London rather than in digs. I’d ring him now and again to see if everything was all right. He just got his head down and worked at his game.
“Educationally, he was top grade, and the lad could play. The phrase I used at the time to his mother was ‘special talent’ and she said that on a summer holiday in Majorca, Bayern Munich were doing a coaching camp and a Bayern coach had said the same thing.”
At Tottenham, McKenna progressed. He earned a first professional contract and moved through the youth team into the reserves and first-team squad.
McKenna playing for Tottenham’s reserves in 2006 (Adam Davy/Getty Images)
It was a time of managerial flux at Spurs — Hoddle was there from 2001 to 2003, followed by David Pleat (caretaker), Jacques Santini and Martin Jol. In August 2004, three months after turning 18, McKenna was used by Santini as a second-half substitute in a pre-season friendly at Celtic. “I was at it!” McKee says. “It shows you Kieran could play, he was no fool.”
McKenna had captained Northern Ireland at under-17 and under-19 level. He had faced players such as Germany’s Manuel Neuer and Kevin-Prince Boateng in the European Under-19 Championship in 2005. His midfield contemporaries at Tottenham were players such as Tom Huddlestone and Jamie O’Hara — after a 2-0 win over Fulham reserves in 2005, the encyclopaedic fan website Spurs Odyssey described McKenna as playing “like the dynamo he is”.
That season — 2005-06 — Spurs won the southern section of the reserves league but lost 2-0 to Manchester United in the play-off final at Old Trafford, with goals from Gerard Pique and Ole Gunnar Solskjaer. McKenna played 20 times. He was 19.
But then came the pelvic problem that would, at first, niggle at McKenna’s embryonic playing career, then, in November 2008, end it.
“One of the guys in the academy said that Kieran had a hip injury and he was struggling,” recalls McKee. “This is where the credit is 100 per cent his: how many kids go across the water (from Ireland to England), pick up an injury, think, ‘Woe is me’, come home and disappear?
“What did he do? He got his head down and got into coaching. What he is and who he is, that’s down to Kieran. He did all his coaching badges through the English FA, did his Pro Licence at St George’s Park. Tottenham would have facilitated the start of it.
“But that in itself is a big thing — you’re an outsider.”
McKenna drives with the ball for Northern Ireland Under-21s in 2007 (Oliver McVeigh/Getty Images)
Connolly agrees: “It must have been heartbreaking for him. It’s hard. You go for an operation you think is going to cure it, but it doesn’t cure it. But, rather than feel sorry for himself, Kieran thought he’d go another way.”
McKenna has spoken of the encouragement he received from senior players at Spurs such as Les Ferdinand and Tim Sherwood, and there was the practical assistance given by coaches John McDermott, now the FA’s technical director, and Alex Inglethorpe, academy director at Liverpool.
He chose Loughborough University to study sports science, where he would coach students and spend time working at nearby Nottingham Forest with their under-10s and under-11s. Summers were spent coaching in New York and Vancouver.
“I knew Kieran from when he had finished at Tottenham and went into university at Loughborough,” says Jamie Robinson, who was then with the Professional Footballers’ Association (PFA) and who became another influential coaching voice in McKenna’s new life. Today, Robinson is coaching San Diego Wave, having been one of Steve Cooper’s assistants at Forest.
“I got the sense Kieran was quite stoic about his playing career. I suppose for young players, when they realise it’s not going to happen, it’s how they take that disappointment — it can either be fuel for whatever’s next in football or they kind of put football behind them and go into another walk of life.
“The PFA had, and has, a coaching department that helps players with their transition from playing to coaching. Kieran came along on our UEFA B course and myself and Brian Borrows did his final assessment at Loughborough University. He took the university’s first team — he didn’t play for them — when he was 22 or 23.
“We saw unbelievable potential, one of the best candidates I saw at UEFA B (coaching badge) level. You could see he was a real student of the game — that’s an overused phrase, but it genuinely does describe him.
“Kieran studies the game, as opposed to doing a course. He wanted to think about how he did his work and he had a terrific manner with the players. He had detail and tone, the ability to motivate and get his ideas across. He was really impressive.”
McKenna’s father, Liam, once told Connolly a story reflecting that “terrific manner”. Sitting in a van from the hotel in Enniskillen McKenna’s parents ran until 2023, Connolly says, “All the chat was about Kieran.
“Liam was talking about when Kieran went to Loughborough, he was driving a car, top of the range. Kieran sold it. He bought a bicycle, so he would be going to college the way every other student was going. Other boys would have been, ‘Look at me’. Not Kieran. He just wanted to be part of the group. No airs and graces with Kieran. Intelligent isn’t a big enough word. He’s well switched on.”
Robinson witnessed McKenna do his UEFA A badge and then his Pro Licence, completed in 2017 at English football’s headquarters, St George’s Park.
“Kieran delves into the next layers rather than just taking what’s given to him,” Robinson says. “I found that when trying to stimulate curiosity. There’s not much time together — it’s not a PhD in football coaching, they’re vocational qualifications, short courses and the work you do away from the course, away from St. George’s Park, is the key bit.”
After Loughborough, McKenna returned to Tottenham to work in the academy, moving up to take the under-18s — and this was when Northern Ireland Under-21 manager Jim Magilton invited the 29-year-old coach to one of his side’s camps in March 2016. Magilton’s squad were about to play their last group game in European qualifying, in Paisley against Scotland.
“I knew of Kieran when he was an under-age international — ‘This lad Kieran McKenna’,” Magilton recalls. “Then people started mentioning Kieran at Tottenham, a lot of talk about ‘this young Irish coach’. He was getting attention.
“I’d heard so much I thought it was a great opportunity to bring him in to add to his CV. We had a conversation and right away I was drawn to his enthusiasm. I brought Conall Murtagh (now first-team fitness coach under Arne Slot) in from Liverpool as well — I’d heard about them both.
“I had more to do with Kieran that week and there was a ‘wow’ with Kieran, how he presented himself within the staff, his communication, man-management, sheer enthusiasm for the game. Then as the week progressed, his detail and knowledge. He was still so young. I was just really impressed.
“Preparation for him is key. Tactically he is so astute. He was turning theory into practical sessions. The other thing is, it’s fine talking about all this to the other coaches but it’s doing it with the players; the roles and responsibilities were made very clear, individually and as a team. At Ipswich you see that, you see coaches with iPads on the bench, it’s active information and you see Kieran going over to them. Sam Morsy and Conor Chaplin have talked about how proactive Kieran is at half-time.”
Not long after that under-21s experience, McKenna was lured from Spurs to Manchester United. There, he worked with Jose Mourinho, Solskjaer and Michael Carrick. Before Middlesbrough played Ipswich last season, Carrick looked at McKenna’s work at Ipswich and before and called him “a natural” coach.
“The Brighton interest was no surprise to me given how they select and recruit players and managers, the due diligence,” Magilton says.
Ultimately, McKenna stayed and it is Liverpool at Portman Road on Saturday, a first meeting there since 2002. That is the change McKenna has brought to Suffolk.
Back in Blakes of the Hollow in Enniskillen, they will be watching. The bar is the shirt sponsor of McKenna’s old club, where brother James is now coach. In February, the two arranged a trip for a young group to Portman Road.
Town Lads bringing the luck to IPWICH pic.twitter.com/e5SQyHm1U6
— EnniskillenTownFc (@EknTownfc) February 24, 2024
“Kieran spent the whole day with the boys,” says Connolly. “He took them to the training ground, to the stadium, sat in the dugout with them, watched the TV game in the hotel with them, went out bowling with them.
“Enniskillen is hugely delighted. It’s amazing that somebody formerly part of your club will be managing in the Premier League.”
(Photo by Stephen Pond/Getty Images)