23-year-old midfielder James Olayinka is on trial with League Two side Swindon Town.
Despite the transfer window closing over a week ago, Olayinka is a free agent after being released by League Two club Cheltenham Town after their relegation to the fourth tier. The former Arsenal academy player has also experienced loan spells at Northampton Town and Southend United before he permanently moved to Cheltenham on deadline day in 2022.
Despite making only four appearances for the Cobblers, Olayinka was a part of the Northampton team that achieved promotion to League One in 2020. He made 21 appearances for Southend, scoring three goals in the process. Despite the majority of his appearances coming off the bench for the Robins, the 23-year-old made almost 50 appearances, scoring one and assisting a further three in all competitions.
Swindon manager Mark Kennedy confirmed that Olayinka was on trial with the club when speaking to the press.
“James has been in. I know James very well from playing against him, he is a very talented boy, technical, final third creativity, and has really good skills. He has found himself in a very unfortunate situation, I struggle to understand why he has not got a club but he has found himself there and so I think we have been good for each other in that regard. He has done very well. We have brought him in to have a look at him; Marcus (Bignot) has worked with him for over a year and I remember playing against his teams and when we were doing our match prep, he was a real standout.
“I have said to him ‘If somebody knocks on your door before we do and they offer you a contract, we will wish you well’ but he has done really well and has certainly enhanced our training. Having a trialist in gives you a chance to look at people, there are millions of reasons to have one in but ours are always with a view to looking at someone properly. It is not a secret otherwise we would have said to Callum (Knowles) ‘Can you not get them in.’
“We have had a couple in that we really liked but what happens down the line on that, I don’t know. We are not down the line on signing anybody, for lots of different reasons. So, we have had lots of trialists in but are we going to sign somebody in the next three or four days? No, definitely not.”
The fact that Olayinka hasn’t been picked up by a club yet is surprising. Although he was inconsistent at Cheltenham, he played his part in keeping the side in League One under Wade Elliot in the 2022/23 season.
Although he fell out of favour and was subsequently transfer-listed last season when the side was managed by Darrell Clarke, he managed to bide his time and get back into the squad on the final matchday of the season. Unfortunately for Clarke and Cheltenham, a loss on the final day condemned them to the fourth tier, which meant the end of Olayinka’s stay at Whaddon Road.
The 23-year-old needs a side to call home as he looks to relive the highs of playing at Arsenal. With him jumping clubs a worrying amount in the last four years, he needs a club to settle in at. However, for a player, coming in with five matches already played in the league is never ideal, and it may take a while for the Englishman to break into the Swindon starting XI if he is to be signed by the club.
