Middlesbrough told to consider terminating contract of £2m flop - "I feel really sorry" | OneFootball

After two years at The Riverside, Micah Hamilton's Boro career has flat-lined, and FLW's fan pundit is sad over the way things have panned out.

Middlesbrough's 2026-27 season could be shaping up to be a successful one, but that doesn't apply Micah Hamilton at the moment.

With three wins from their first five games of the 2026-27 season, Boro are well-placed for another shot at a return to the Premier League.

Following disappointment at the end of last season, when they lost the Championship play-off final to Hull City, they've regrouped over the summer, brought in fresh reinforcements, and seem well positioned to challenge near the top of the division again, this time around.

But not everyone at Middlesbrough has had a happy time of things, of late. Micah Hamilton's arrival from Manchester City in 2024 was an opportunity for the young winger to kick-start his senior career in the Championship, but instead he's almost completely disappeared from view. He's only managed 17 League appearances in that time, and has only appeared on the pitch for them for four minutes in the whole of 2026, so far.

Furthermore, Boro's attempts to offload the player over the course of the summer came to nothing, with reports that he wasn't even involved in their pre-season preparations, instead being permitted to go on trial with several clubs as all concerned searched for a move away. But this failed to materialised, and Hamilton hasn't even been included in their squad yet in 2026-27.

Surprise expressed over Micah Hamilton flopping at Middlesbrough

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In order to try and make some sense of what has happened to Micah Hamilton since his transfer to Middlesbrough, Football League World have spoken to our Middlesbrough fan pundit Liam Day, but Liam is as flummoxed as anybody else over why this move has been such a disaster, especially since he held out such high hopes for the winger when he first arrived at the Riverside.

"I feel really sorry for Micah Hamilton," Liam told FLW.

"I remember when we signed him, I was really excited. It seemed like a signing of "Wow, we've got a good one here, he's guaranteed to go on to be a big name in the future.

"But I don't know what's gone wrong with him. Quite clearly there's been something. There's no guarantees in football, but I know I thought "Wow" when we signed him, and I feel really sad for him that it's not happened, but that's football."

"Am I surprised that no team's taken a chance on him? Not really, because what's he done to prove that he deserves one? He's not done anything for the last three years, and while he hasn't really had much opportunity at Boro, he's clearly doing something wrong which proves that he doesn't deserve one."

And Liam feels that, at this stage, the best option for all concerned might be to part ways, even though Hamilton's contract still has almost a season left to run.

"I think the best case scenario for all parties is a mutual termination of his contract," Daly added.

"Will that happen? I don't really know, but I really wish him all the best. He seems like a nice enough lad."

Now that the transfer window has closed, Micah Hamilton & Middlesbrough are stuck with each other until 2027

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There could be a multitude of reasons behind why the transfer of a player from one club or another might not work out, and these reasons are often amplified when that player is young. A failure to adapt to new surroundings, homesickness or a loss of motivation or confidence are just three of the possible explanations for this transfer having not worked out.

Few would doubt that Micah Hamilton has the raw talent to be able to succeed as a player. He was on the books of one of the wealthiest and most powerful clubs on the entire planet for eleven years, and the only goal of his senior career so far came just 19 minutes into his full his debut for them, in the Champions League against Red Star Belgrade in December 2023. He was also capped by England at the under-16 and under-20 levels.

But Hamilton's time at Middlesbrough has not panned as anyone might have expected. Over two years, he's managed just 21 appearances for them in all competitions, and he's managed neither a goal nor an assist over that time. A loan move to Stockport County in January 2025 didn't go any better. Over the course of half a season, he managed just five appearances for the Hatters, all of them coming from the bench, during which he got just 63 minutes of game time.

There are alternatives to cancelling his contract, but with the summer transfer window now having closed, none of those can now happen until January. It's possible that there will be a club who'll take a chance on him - either as a permanent signing or, more likely, on loan, but until the start of the new year, unless Middlesbrough are prepared to take the financial hit of just letting him go, it now seems that Micah Hamilton and his club are stuck with each other until the start of 2027, at the very least.