Dermot Drummy
From TheChels.info - The Chelsea Football Club Wiki
Dermot Drummy (born 16 January 1961) was a coach who formerly worked in the academy Chelsea.
Pre-Chelsea
A schoolboy footballer at Arsenal, Dermot's playing career was unremarkable, falling from Blackpool at the age of 19 to a non-league career in the south of England.
In 1996, he joined the Arsenal coaching staff at their academy in Hale End, Walthamstow. There, he worked his way up to manage the Youth Team, and worked with a number of talented young players, including Ashley Cole.
Chelsea career
In 2007, Dermot accepted a move to Chelsea, where he would be in charge of the club's Under-16 team, the final stage before players leave school and sign scholarship deals. In December 2008 he was promoted to manage the Youth Team, at Under-18 level, when Paul Clement was made permanent Reserve Team Manager. Later that season, when Luiz Felipe Scolari was sacked, he worked with the Reserve team on an interim basis as Clement joined the first team coaching staff.
In 2009-10 Dermot led the academy to the FA Youth Cup Final, their second appearance in three years, in which they beat Aston Villa 3-2 on aggregate over two legs.
After another season in charge of the youth team in which the Youth Cup defence reached the Semi Final stage, Drummy was promoted to the role of Under-21 Manager, replacing Steve Holland, who had joined Andre Villas-Boas' first team squad coaching staff.
He secured a national title success in 2014 when his young team finished [of the standings] before going on to beat Manchester United at Old Trafford in the [final]. Weeks later he changed roles within the club, 'moving upstairs' to take on a newly-created role as Head of International Coaching as part of the Chelsea Foundation.
He left this post the following year and chose to pursue a first-team role elsewhere. Having entertained the idea of coaching in Brazil with Bangu, he was eventually named as Crawley Town manager for the 2016-17 season, a post he was dismissed from before the end of the campaign despite having led the club to a relatively respectable league position.
Dermot sadly passed away in December 2016.