James "Jimmy" Dean Smith (born 7 January 1987) is an English retired professional and semi-professional footballer who played as a winger / midfielder last attached to Grays Athletic. He is also currently a youth coach at Chelsea, and features occasionally for the U23 side. Smith began his career at Chelsea at the age of nine, progressing through the youth ranks before signing professional terms with the club in 2005. After featuring regularly for Chelsea's reserve side during the 2005–06 season, Smith made his first-team debut in May 2006. It turned out to be his only appearance for the club. The following season, he joined Championship side Queens Park Rangers on a season-long loan agreement, before spending three months on loan at Norwich City towards the latter months of 2007. Smith was loaned out once again ahead of the 2008–09 campaign, spending the first half of the season with Sheffield Wednesday. He returned to Chelsea in January 2009, only to join League One side Leyton Orient on a loan deal for the remainder of the season. Smith signed for Orient on a permanent basis in July 2009, signing a two-year contract. He spent four seasons with the club, making over 180 appearances in all competitions. He was released by Orient in April 2013, and signed for Stevenage ahead of the 2013–14 season. Smith signed for League One side Crawley Town in May 2014 for an undisclosed fee and was later made club captain, he spent six years with the Sussex club making over 160 appearances. Smith ended his professional playing career at Yeovil Town in 2021, after which he took up a position at Chelsea as a coach. However, he resumed his career at semi-professional level with Harlow Town later the same year. Smith has represented England at various youth levels. Club career Chelsea Smith joined the Chelsea Academy aged nine and worked his way through the various youth levels. He signed for the club on professional terms at the age of 18 in 2005, and subsequently made the step up from the academy squad to playing regularly for the reserve side. An attacking midfielder by trade, who can also play on both wings, Smith finished as the reserve side's top goalscorer for the 2005–06 season, predominantly playing in his preferred attacking midfield role. He was made captain of the reserve side during the season. After his impressive season for Chelsea's