RICHIE Holland admits he couldn’t turn down the opportunity to work with John Caulfield.

‘John's a legend in the League of Ireland, firstly as a player and now what he's done as a manager,’ Holland says, as he settles into his new role as Caulfield’s assistant manager at Galway United.

‘To work with him day-to-day and see how he manages people and groups and how he manages the club, that’s a great insight and great learning for myself in terms of where I am in my career.

‘It was too good of an opportunity to turn down,’ he tells this week’s Star Sport Podcast.

This is also the meeting of two West Cork minds – Caulfield has called Enniskeane his home since 1985, while Holland hails from Bandon, just ten minutes away.

Their paths have crossed before. When Caulfield was manager of Cork City (2014 to 2019), he handed Holland a coaching break in 2017. He rang the Bandon man, who had just finished up as Kennedy Cup manager with the Cork Schoolboys League, and asked him to get involved with the Cork City U19s alongside Cormac Cotter and Colin Healy.

Nine years on, Holland has answered Caulfield’s call again, joining forces in Galway with a shared ambition: to push the team as far up the Premier Division table as possible.

Galway United manager John Caulfield.

Since he took the reins in 2020, Caulfield has masterminded the club’s rise, guiding Galway to the First Division title in 2023 and establishing them back in the top flight. Just last November, Caulfield signed a new two-year contract, and his enthusiasm is not waning.

Holland recalls his first training session with Galway. It was freezing, and he came prepared, hat and gloves packed. He turned around to see Caulfield, now 61, jogging out in a pair of shorts. Standards set. Time to get to work. This is exactly the kind of learning Holland wants – the chance to pick the brains of a man who has won titles and cups and survived for decades in a cut-throat environment.

It represents the natural progression in a coaching career that has already included spells with Cork City and Cobh Ramblers, initially as assistant coach and later stepping up as interim manager with both.

‘This is the next step for me, to work closely with a top, top manager,’ the Bandon man explains.

‘It’s been a long story to get here. I started with my home club in Bandon as a player and went into coaching too. It was when I went to Cork City as a player with their U21s that the coaching took off.

‘I had an injury so I started my coaching badges while I was out. Mick Conroy and Paul Bannon gave me an opportunity to manage a team while I was injured – that was my first introduction to coaching.’

Coaching comes naturally to Holland. He jokes that, as the oldest of five brothers growing up, his mother gave him plenty of responsibility. Leadership is something he has long been accustomed to. So when he reached a crossroads in his Cork City playing career and realised he wasn’t going to get a new contract, Holland knew coaching was his route to remain in the game.

‘I wanted to stay in football, build a career, and the next best thing to playing was going coaching,’ he says.

He began his apprenticeship at home with Bandon AFC, then worked under Conor Uhl with the West Cork Schoolboys League for two Kennedy Cup campaigns.

In 2017, he became the first Cork recipient of the Noel O’Reilly FAI Coach of the Year award. With Cork City, Holland held various roles – U19 assistant manager, first-team coach and a short spell as interim manager in 2023.

Richie Holland with former Republic of Ireland boss Martin O'Neill after he won the Noel O'Reilly FAI Coach of the Year award in 2017.

Last season he joined Cobh Ramblers as assistant manager and head of development, and again found himself stepping in as interim boss late in the campaign. He also handed Clonakilty’s Ethan O’Donovan opportunities to train with the first team, while continuing his own education by completing a Masters in Applied Sports Coaching at the University of Limerick last year.

His influences include notable figures, among them two more high-achieving Bandon men: Niall O’Regan, the FAI’s Head of Education and Development, and Conor Hourihane, now manager of Barnsley.

‘Funny story,’ Holland smiles. ‘We just signed a player, Conor Barrett, from Barnsley, and I was able to pick up the phone to Conor and have a conversation with him about that signing. So you’ve two lads from Bandon having that discussion over players – it was surreal.’

Hourihane is an example of how hard work pays off. So too is Holland’s own story, and he has the sleeves rolled up for his latest challenge. He’s encouraged by what he has seen on and off the pitch in the early stages of the season.

‘There’s a big transition here – we've brought in 13 new players,’ he explains.

‘John has worked miracles in terms of where the club was when he came in to now being established in the Premier Division, and in a shout of getting into Europe last season.

‘The environment here, the culture John sets around the place, is brilliant. All he asks is that everyone works hard every day so when you get home you know you’ve given your best.

‘He has a clear identity in terms of the way his teams play and the values he instils are important: work hard, be organised, have a clear plan going into every game.

‘We want to stay in the league, first of all, and then push up the table. The environment and culture will dictate that.

‘It's about us believing every day that we can be the best we can be and be competitive. Look at the draw away to Shelbourne, one of the title favourites – to go there and put in that performance will hopefully bring confidence to the lads.’

Under the guidance of Caulfield at Galway United, Holland has entered the next phase of his own story – an opportunity to learn from a legend while also shaping his own future as a coach and, maybe one day, a manager.