Middlesbrough's decision to release midfielder Alex Gilbert at the end of last season has been resolved, with the 24-year-old confirming a three-year deal at League One side Leyton Orient. Because he was a free agent, Gilbert was able to complete the move outside of the transfer window.

Forty Championship appearances for Boro

Gilbert made 40 appearances in the Championship for Middlesbrough, giving him a fair grounding in second-tier football before his departure this summer. That record will have attracted interest from clubs across the Football League, and Gilbert indicated the decision on his next club was one he took carefully.

"I was happy to be patient to make sure I made the right decision," Gilbert told Orient's website. "I spoke to a number of clubs over the summer and believe that Orient is the best place for me."

His patience, at least in terms of public announcements, appears to have paid off. Signing a three-year contract at this stage of his career gives him security and a clear platform to establish himself at a new club.

A play-off final connection

There is a certain symmetry to the move. Gilbert spent part of the 2024-25 campaign on loan at Charlton Athletic, where he was part of the side that won promotion from League One via the play-offs in 2025, beating Leyton Orient in the final. He has now moved to the club he helped defeat at Wembley, which lends the signing a notable backstory.

Orient head coach Richie Wellens was unambiguous about what attracted him to the player. "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 10."

That versatility, operating in either a box-to-box or a more advanced midfield role, will have been an important factor given the demands of the League One schedule.

What it means for Middlesbrough

For Boro, the Gilbert departure is one of several squad changes made during this window as Michael Carrick looks to shape his group for the Championship campaign ahead. The club has already moved to bring in Sam Byram on a free transfer and signed Pukstas from Hajduk Split, suggesting the recruitment team have been active in building cover and quality across the pitch.

Releasing Gilbert, who had accumulated meaningful second-tier experience during his time at the Riverside, represents a judgement call on the club's part about the balance of the squad and where investment in midfield is best directed. With 40 Championship appearances to his name, Gilbert will be considered a useful addition at League One level, but from a Boro perspective the move draws a line under a chapter rather than opening one.

Gilbert joins a Leyton Orient side that will be competing in League One this season after narrowly missing out on promotion in the play-off final. For Middlesbrough's supporters, the focus remains on what the club does next in the Championship, where the opening weeks of the season will quickly clarify whether the summer business has strengthened Carrick's options sufficiently.

Frequently asked

Why did Alex Gilbert leave Middlesbrough?
Gilbert was released by Middlesbrough at the end of the 2024-25 season when his contract expired, making him a free agent.
How many times did Alex Gilbert play for Middlesbrough in the Championship?
According to reports, Gilbert made 40 appearances in the Championship during his time at Middlesbrough.
Can a free agent sign outside the transfer window?
Yes. Players who are out of contract and classed as free agents can sign for a new club at any point in the season, regardless of whether the transfer window is open.