Jack Wilshere will laugh hardest as Spurs hand Luton Town serious transfer gold | OneFootball

Former Arsenal midfielder Jack Wilshere is benefiting from Tottenham Hotspur's decision to loan Luton Town Jamie Donley

Tottenham Hotspur fans may not have the greatest relationship with Jack Wilshere, given his playing days with Arsenal and West Ham United, but the 34-year-old is currently being tasked with bringing the best out of one of their young stars.

There arguably haven't been many more exciting attacking midfielders to come out of the Spurs academy in recent years than Jamie Donley, who was a goal-contribution machine for the youth squads at Hotspur Way in the early 2020s.

From netting 16 and assisting six for the under-18s in the 2021/22 campaign to scoring six and assisting 14 in 20 PL2 games in 2023/24, it's understandable why Tottenham handed him a five-year deal before loaning him out to Leyton Orient in the summer of 2024.

And that year at Orient proved why, too. However, a dud year last season has him back in League One, and the former Arsenal midfielder looks to be benefiting from that the most.

Jamie Donley conquered League One with Leyton Orient in 2024/25

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Two years ago, a 19-year-old Donley was sent out on his first senior loan to Leyton Orient, the side that had finished 11th in their first season back in League One for nine years.

Not many had Richie Wellens' side as promotion hopefuls, but a mixture of some promising current players and three excellent loan signings — Josh Keeley, Charlie Kelman and Donley — helped the O's finish sixth, their highest league finish in 11 years.

It took a while for the creative midfielder to find his feet in the squad, though, and Orient actually began the campaign dwelling in the lower mid-table. It wasn't until December that Donley got regular starting minutes, and that coincided with a 15-game run where Richie Wellens' side won 12 and lost just once.

In that period, the Spurs loanee scored six and assisted five, and after a run of defeats, they then won six of the final eight games to finish in the play-offs. Donley ended his first proper senior campaign with eight goals and 10 assists.

Why Jamie Donley is now back in League One, despite that Leyton Orient season

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It was evident that, even if Leyton Orient didn't get promoted, and in the end, they lost in the play-off final to Charlton Athletic, Donley would be moving on to the second tier without them, and Stoke City were the side to land him on loan last summer.

The Spurs loanee had made his senior debut for Northern Ireland towards the end of the 2024/25 term, too, so he had plenty of momentum to take into his time at the bet365 Stadium. Unfortunately, that momentum got derailed almost immediately.

Donley assisted on his league debut off the bench for Stoke against Derby County, and it all went downhill from there. He made just four substitute appearances in the Championship for the Potters, being left on the bench 13 times.

The Northern Irishman was promptly recalled in January and sent back out on loan to Oxford United, and despite the Yellows' relegation, the 21-year-old played a strong part in what was a much-improved second half of the season under Matt Bloomfield.

Jamie Donley likely could have landed another Championship move, but is back in League One

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Donley ended the season with one goal and one assist in 13 second-tier games for Oxford.

While not spectacular, there'd be some expectation that being with one club who'd play him all year in the Championship could lead to the 21-year-old taking those necessary next steps many felt he'd be taking last season.

But he's landed back at a top-end League One club, playing for Luton Town, who are looking to get back into the second tier following back-to-back relegations from the Premier League a few years ago.

The Hatters were one of the pre-season favourites to go up this year, given how well they ended last term under Jack Wilshere, going unbeaten in their final 12 games, which included the EFL Trophy final, to finish just shy of the play-offs.

Signings like Donley will do no harm in achieving those expectations.

Jamie Donley has already shown his promise under Jack Wilshere

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Given how much expectation there is to break into top-flight football in the early stages of your career, Donley, who turns 22 in January, may be seeing his long-term future at Tottenham fading if he's unable to get back on track this season.

It's been so far, so good for him under Wilshere, though, who knows what it's like to have pressure on young shoulders.

Donley netted his first for the club against former club Leyton Orient on Saturday, following up on registering an assist on his home debut against Stockport County last Wednesday. If he can carry on this vein of form, he could easily match, or even eclipse, the 18 goal contributions he managed two years ago.

Spurs will want Donley to hit those heights and prove he is much better than third-tier level. If it means Jack Wilshere achieves success in the dugout, then so be it.