Leyton Orient have moved to bolster their midfield by signing Alex Gilbert on a three-year contract, the club confirmed. The 24-year-old arrives as a free agent after being released by Middlesbrough at the end of last season, meaning no transfer fee was required and the deal could be concluded outside the standard transfer window.

Background and experience

Gilbert comes to Brisbane Road with a solid recent track record at this level and above. According to the BBC, the midfielder made 40 appearances in the Championship during his time at Middlesbrough, demonstrating that he can more than hold his own in a high-tempo, physical environment.

Most pertinently for Orient supporters, Gilbert also has direct League One experience. Last season he joined Charlton Athletic on loan, where he was part of the side that won promotion from the third tier via the play-offs. In a detail that adds an intriguing edge to his arrival, that Charlton team beat Orient themselves in the 2025 play-off final, meaning Gilbert has experienced the pain of this club's supporters at close quarters before now committing his future to them.

What the club and player said

Orient head coach Richie Wellens was enthusiastic about what the signing offers tactically. "Alex has proved in recent years that he can be a really good player at this level," Wellens said. "He is a threat from set-plays, in terms of his delivery from dead-ball situations, and he can play as either an eight or a ten."

That flexibility in the middle third is a notable asset. A midfielder who can operate as a box-to-box eight or as a more advanced ten gives a manager options in how he shapes his team from week to week, and Wellens appears to value the versatility highly.

Gilbert himself indicated he was in no rush to secure a new club after his release, and took time to assess his options before committing. "I was happy to be patient to make sure I made the right decision," he said on Orient's official website. "I spoke to a number of clubs over the summer and believe that Orient is the best place for me."

What this means for Orient

Arriving as a free agent, Gilbert represents the kind of low-risk, potentially high-reward recruitment that third-tier clubs often rely on when the summer window closes. Because he was without a club, the signing is not bound by the standard transfer deadline, giving Orient the flexibility to add him to their squad whenever they felt the deal was right.

His set-piece delivery, highlighted by Wellens, could prove particularly valuable over the course of a long League One season, where fine margins in dead-ball situations can separate clubs competing for promotion or trying to avoid the drop. Orient will be hoping that a player who was on the opposite side of their most painful recent moment can now help them push in the other direction.

The three-year length of the contract is also significant: it suggests the club view Gilbert as a genuine building block rather than a short-term fix, and gives both parties the stability to develop a working relationship over time.

Frequently asked

Who is Alex Gilbert and where did he play before signing for Leyton Orient?
Alex Gilbert is a 24-year-old midfielder who was previously at Middlesbrough, making 40 Championship appearances for the club. He also had a loan spell at Charlton Athletic last season, where he helped them win promotion from League One via the play-offs.
How long is Alex Gilbert's contract at Leyton Orient?
Gilbert has signed a three-year contract with Leyton Orient. He joined as a free agent after being released by Middlesbrough, so no transfer fee was involved.
What position does Alex Gilbert play?
Gilbert is a central midfielder who can operate as either an eight (box-to-box) or a ten (advanced playmaker), according to Orient head coach Richie Wellens. He is also noted for his delivery from set-pieces.