 Baldwin, born in City of London, failed to make an appearance for the Chelsea first-team, and was released by the club at the end of the 2001–02 season.He had spent ten years as a trainee for the London club, working under Steve Clarke and training alongside the likes of John Terry, Frank Lampard and Eiður Guðjohnsen, with Carlton Cole and Robert Huth in the same youth team as Baldwin.Baldwin was loaned out to St Albans City in the Isthmian League in 2003, where he made three appearances for the club.