It was no shock to see Boro’ make an early move in the 2023 January transfer window; Jake Forster-Caskey first through the door. What was maybe a shock, however, was the fact we secured the midfielder in on an actual, permanent deal. At the time, Forster-Caskey’s Charlton Athletic teammate Alex Gilbey was with us too. Having said that, Gilbey was on loan. When reports first broke that JFC could be joining him, it felt like another temporary deal was most likely too. Instead, we made him ours and persuaded the Addicks to let him go.

It’s fair to say the midfielder came with some Football League pedigree too. Sadly, his time at the Lamex was hampered by injury; his time at the club restricted to just 58 outings over a two-and-a-bit-year spell. Of what we saw of him, there was no doubting his talent and quality. And he certainly still had enough about him to make an impact in both the fourth and then third tier. In summer 2025, however, Boro’ confirmed that Forster-Caskey would not be offered a new contract and was allowed to leave for pastures new.

Jake Forster-Caskey: Before Boro’

A native of Southend, the midfielder’s career actually started on the Sussex – not Essex – coast. Brighton & Hove Albion was his first club; starting out with the Seagulls as a youth player in 2007. Three years later, he penned the scholarship deal that would move his career up a gear. Lo and behold, the next day saw him named as an unused substitute for the first team. As a bairn, however, game time was restricted while at Brighton. So, it’s no wonder a flurry of loan deals saw him gain experience elsewhere.

First came Oxford United, before Forster-Caskey had two loan spells at MK Dons. Rotherham United became the third, and final, club to provide a short-term home for the midfielder while he was still with the Seagulls. That was something that came to an end in January 2017 though; the player snapped up by Charlton Athletic on a two-and-a-half year deal. A serious injury kept him out for much of the 2018-9 campaign – but it didn’t prove enough to stop him earning a new deal with the Addicks in summer 2019.