Paul Fennessy

JAMES OLAYINKA’S SIGNING was announced on 15 December, but it would be fair to say he is still getting to grips with his new life in Derry.

More than two months later, the player is still searching for permanent accommodation as he currently lives in a local hotel — far from the first Irish-based person to be left frustrated by the housing market.

“I’m just trying to find somewhere at the moment so I can then get settled and get things across [from England] and be in one location,” he tells The 42.

“So it’s a bit difficult day to day, difficult in the evenings. But thankfully, we have a chef, so I can get meals from him.

“But obviously, I’m looking at the moment, going for viewings all the time, so hopefully it can get sorted quickly.”

It is Olayinka’s second season playing in Ireland.

Last year, the 25-year-old impressed with Waterford, featuring 33 times in all competitions.

He describes his departure from the RSC outfit as “a weird situation”.

He adds: “There was an option for me to stay, and I’m still not fully sure what happened in terms of a mix-up, and it was a bit difficult because there was no manager in place at the time towards the end of the season, because Lawsy [Matt Lawlor] was leaving.

“And that deadline just went by without hearing much, and then after that, it was just a case of deciding whether I was going back to England. And Derry called, and I just thought it was a good opportunity.”

The Londoner did have offers closer to home but felt there was a sense of “unfinished business” with regard to his time in Ireland.

The 25-year-old sees the Candystripes as a club going in “an upwards direction” and is optimistic about their prospects for the 2026 campaign.

“I think the ideal season would be winning the league and getting to the group stages in Europe,” he says.

Last year was Olayinka’s best-ever tally of individual appearances as a professional, and the player is hoping to eclipse that record this year, though he has got off to a frustrating start.

The midfielder has been an unused sub in all three of Derry’s league fixtures so far, as well as their President’s Cup clash.

Nonetheless, Olayinka will be hoping to get a chance at home to his former club tonight, particularly in the wake of last week’s disappointing 1-0 loss against Bohemians.

James Olayinka pictured playing for Waterford last year. Ryan Byrne / INPHO Ryan Byrne / INPHO / INPHO

An injury that was carried over from his time at Waterford and which had to be managed carefully in the off-season has also contributed to his lack of minutes so far.

And it is not the first time Olayinka has had to demonstrate patience.

He spent 16 years on the books at Arsenal, joining the club as a six-year-old before signing a professional deal in 2019.

A competitive first-team appearance proved elusive, though he came close, making the bench on a couple of occasions, including the 2020 Community Shield match with Liverpool.

While he didn’t fulfil his dream of representing the Gunners in the Premier League, the club gave him “a real platform”.

Olayinka cites Aaron Ramsey, David Luiz and Mesut Ozil among the players he studied carefully and tried to learn from at the Emirates.

“Sometimes it’s just about timing,” he adds. “I think we were around eighth [in the Premier League] at the time, and not doing too well. So during that period of transition, it became more about focusing on the first team, and then obviously the overhaul into the new foundations of the squad that you see today.”

His development was also hampered by a disastrous start to a loan spell with Northampton Town in January 2020.

A man-of-the-match display on his debut amid a 3-0 win over Scunthorpe was overshadowed by a serious injury he sustained towards the end of the game after being the victim of a “really bad tackle”.

The season was also interrupted by the Covid pandemic, although Olayinka did return in time for the June playoffs, featuring in both legs of the semi-final and final, as the team secured promotion to League One.

The next season saw the player back in League Two in another loan spell, albeit for a Southend United side short of confidence, who would suffer their second successive relegation that campaign.

Olayinka did at least enjoy substantially more game time, making 20 appearances in the league, though it was not enough to prompt a first-team breakthrough at Arsenal.

In September 2022, the midfielder consequently joined Cheltenham Town permanently on a two-year deal. 

He made over 40 appearances across two seasons for the League One outfit, despite an injury-interrupted second year there, though he was released at the end of the 2023-24 campaign following the club’s relegation.

After a couple of months as a free agent, Olayinka joined Waterford the following January and proceeded to gain a new lease of life with the League of Ireland club.

With this latest opportunity, Olayinka remains determined to appreciate every moment and take his chance when it comes.

“I think once you’re comfortable, it is easy to forget what things can be like when you’re out of the game, or you’re injured,” he concludes. “So that’s the biggest thing, not getting comfortable.”