How ex-Man Utd academy star used ChatGPT to negotiate Leyton Orient transfer

Updated: 13 Oct, 2025 • 0 • min read

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How ex-Man Utd academy star used ChatGPT to negotiate Leyton Orient transfer

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Former Manchester United academy product Demetri Mitchell has revealed that he used AI platform ChatGPT to negotiate his move to League One side Leyton Orient.

The 28-year-old, who began his career at Old Trafford and made one Premier League appearance for the Red Devils, completed a free transfer to Leyton Orient this summer after leaving Exeter City.

But instead of relying on a football agent to handle the deal, Mitchell decided to go solo, and sought advice from artificial intelligence chatbot ChatGPT to help structure and negotiate his contract terms.

Mitchell explained on the From My Left podcast:

They [Leyton Orient] sent me an offer, and I started using ChatGPT, asking it how to negotiate a deal, and what to say in it.

I did think I was worth a little bit more as well, but you don't want to be like that, "Oh, yeah I think I should be worth an X amount."

Mitchell added that skipping an agent meant he could keep the fee that would usually go to representation:

Because I didn't use an agent, I got that [agent fee] as a signing-on fee.

An agent might have got me a couple hundred pounds more, but the difference would've been eaten up by their percentage anyway.

Mitchell's Criticism of Football Agents

The former England youth international, who represented the national team from U16 to U20 level, also used the podcast to share his frustration with the agent system in lower-league football.

There's three types of agents.

There's the agent that works for an agency, who's just getting a salary, then you got agent number two, who works for a big agency and they're trying to sign young, up-and-coming prospects and then once you're not one of them prospects anymore, they're not interested.

And then there's agent number three, the one that's got their own business, [that are] just money-hungry. They just want to get moves anywhere and anywhere fast.

When you're in the lower leagues, it's difficult to get a good agent, because that's all you've got to work with.

Mitchell's honest take on football's business side has attracted attention online, with fans praising his self-sufficiency and creativity in navigating a professional transfer using AI tools.

From Old Trafford to Brisbane Road

Mitchell came through the United academy, later enjoying spells at Hearts, Blackpool, Hibernian, and Exeter before his move to Orient.

He's made eight appearances for the O's so far this season and was recently named in Jamaica's preliminary 60-man squad for the upcoming 2025 Gold Cup - a potential international debut on the horizon.

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