There were initially high hopes for the playmaker to become a regular member of the starting lineup having made the step up into the senior ranks during 2019-20.
However, the coronavirus pandemic and injury issues significantly halted his development and led to the Blues going in a different direction.
Almost five years on from his senior debut and having made just five appearances for Chelsea, Anjorin has taken to social media to acknowledge that he is leaving for pastures new.
Who is Anjorin signing for?
At the time of writing, Chelsea had not acknowledged the exit, but it has been widely reported that the 22-year-old will be signing for Empoli.
As per football.london, Chelsea head coach Enzo Maresca is said to have personally recommended Anjorin to the Serie A club.
Having narrowly avoided relegation to the second tier in 2023-24, Empoli have enjoyed a stirring start to this campaign, earning four points from games against Monza and Roma.
Anjorin will now be tasked with trying to break into what appears to be a developing team under boss Roberto D'Aversa.
There is no mention of any fee, yet transfer expert Fabrizio Romano says that Chelsea will possess a 50% sell-on clause.
How has Anjorin's career panned out so far?
Having made his debut as a 67th-minute substitute in an EFL Cup tie against Grimsby Town, Anjorin then received a 19-minute Premier League debut versus Everton on March 8, just before the coronavirus pandemic was officially declared.
Anjorin would have to wait until December 2020 for his next appearance, starting a Champions League fixture against FC Krasnodar before further substitute outings against Morecambe and Barnsley in the FA Cup.
However, stints at Lokomotiv Moscow, where he played nine times before suffering a broken ankle, as well as time with Huddersfield Town and Portsmouth would follow.
More fitness issues restricted him to just 457 minutes in League One during Pompey's title-winning campaign, yet he now has the chance to make a statement in Serie A over the coming season.