James O’Leary back in love with football and enjoying his new role at St Mary's

Every footballer faces a crossroads at some stage in their career — the moment when the game that once brought nothing but joy starts to feel like a burden. 

For 23-year-old James O’Leary of Watergrasshill, that moment arrived earlier this year. 

After many seasons in the League of Ireland with Cork City and Cobh Ramblers, 70 senior appearances for the latter, and three Munster Senior Cup medals, the grind of injuries, travel, and the demands of balancing football with work left him questioning if he had reached the end of his playing journey.

His plan, he admits, was to hang up the boots.

“With work commitments, the injuries, and all the travelling, it was really getting the better of me,” O’Leary reflects. 

"My plan actually was not to go back at all. I thought I was finished.” 

But football has a funny way of pulling you back in. 

For O’Leary, that lifeline came in the form of Craig Hurley, manager in the Munster Senior League, alongside coaches Mick and Morris. 

They reached out to him and convinced him to return to his roots — one of his childhood clubs, St. Mary’s.

It proved to be the spark he needed.

“I had a change of heart after speaking with them, and honestly I’ve loved every single moment so far,” he said with a smile. 

"The lads have been brilliant. They’ve made me feel so welcome, and I’m really enjoying my football again.” 

O’Leary’s love affair with football started in the most traditional of settings — kicking a ball around the back garden with his uncle Pa and big sister Chloe. 

That led to club football with Watergrasshill, where he played from under-7s through to under-14s, before moving on to St. Mary’s at under-15 and under-16 level.

By 2019, his talent was undeniable, and Cork City came calling. 

O’Leary spent two years at the club, developing his game further before making the step into the League of Ireland ranks with Cobh Ramblers in 2022.

His time at Cobh was decorated and demanding in equal measure.

“I loved every minute of my League of Ireland experience. Despite the travelling, it was incredible to test myself at that level. 

"To win three Munster Senior Cups with Cobh and to make 70 appearances is something I’ll always be grateful for.” 

Still, the higher up the ladder you climb, the steeper the sacrifices. When the balance tipped too far, O’Leary made the decision to walk away.

What stands out in speaking with O’Leary now is how refreshed and enthusiastic he sounds. 

The weight of expectation has been lifted, and in its place is the pure joy that drew him to the game in the first place. He has played a crucial part in his sides accumulation of five points from a possible 12, scoring two and assisting two from his left wing position.

“At St. Mary’s, it’s been amazing,” he says. 

"All the lads are fighting for the jersey, and that makes it really competitive. But the atmosphere is great, and it’s a brilliant place to be right now. "My aim is simply to keep enjoying my football and to do the best we can in the league.” 

Hurley’s influence has clearly been pivotal. By encouraging O’Leary to reconnect with his grassroots, he helped reignite a passion that was flickering out. 

It is a reminder that not every career is defined solely by playing at the highest level possible — sometimes, happiness comes in rediscovering the simple thrill of playing with friends, competing for the shirt, and being part of a community.

Football may take up much of O’Leary’s time, but it is only part of his life. 

Away from the game, he works at the Rainbow Club Autism Centre in Mahon, where he supports children and families. 

His own family, too, play a central role in his story.

He lives in Watergrasshill with his parents, Natalie and Jimmy. He is surrounded by his girlfriend Kate, two sisters, two brothers, and a lively group of nieces and nephews who keep him grounded.

“It means a lot to have that support around me,” he says. 

"Football is important, but so is everything outside of it. Having my family and Kate behind me makes all the difference.” 

James O’Leary’s journey is one of persistence, perspective, and renewal. From back garden kick-abouts to League of Ireland nights, from burnout to rekindled passion, his career already spans highs and lows that many players never experience.

At just 23, his best years are still ahead of him, but what stands out most is his outlook. Success, for him now, isn’t about medals or statistics — it’s about playing with a smile again.

“In football, things can change so quickly,” O’Leary says.

“Right now, I’m just grateful to be enjoying it again, surrounded by good people, doing my best for St. Mary’s. 

"That’s all I want.” 

For a player once ready to walk away, that simple truth might just be the greatest victory of all.”