Alex Gilbert is set for a move to Leyton Orient as a free agent after leaving Middlesbrough at the end of his contract, according to a report from The72.
The 24-year-old attacking midfielder has remained without a club since departing Middlesbrough at the end of the 2025/26 campaign, but that spell on the market now appears close to ending. With the transfer window for EFL clubs having slammed shut at 11pm on Tuesday night, Gilbert was set to join Leyton Orient on a free transfer.
Why Leyton Orient make sense
Gilbert was mainly used as a squad player at Middlesbrough, but his versatility and technical ability were highlighted as reasons he stayed in the mix under Kim Hellberg. That background suggests Leyton Orient are adding a player who can offer depth and flexibility without requiring a transfer fee.
For Leyton Orient, the appeal is straightforward. A free transfer gives them another option for the squad while avoiding the cost that would normally come with recruiting a player of Gilbert's profile. For Gilbert, the move offers a path to more regular football in League One after a summer without a club.
The timing also fits a broader reshaping of Middlesbrough's midfield this summer, with several departures and new signings changing the picture there. Gilbert's exit had already left him available, and this appears to be the next step in his career.
There is no indication in the confirmed details that Gilbert turned down Championship interest. What is clear is that, after his Middlesbrough departure, Leyton Orient have emerged as the next likely destination.
