Without much ado he was appointed manager of First Division Chelsea in June 1952. This is so due to the rivalry between the Gunners and the Blues being non existent at the time. Upon Drake's arrival at Chelsea, he made a series of sweeping changes, doing much to rid the club of its previous amateurish, music hall image. He discarded the club's Chelsea pensioner crest and with it the Pensioners nickname, and insisted a new one be adopted. From these changes came the Lion Rampant Regardant crest and the Blues nickname. He introduced scouting reports and a new, tougher, training regime based on ballwork, a rare practice in English football at the time. The club's previous policy of signing unreliable big-name players was abandoned; Drake instead used his knowledge of the lower divisions and the amateur game to recruit little-known, but more reliable players. These included John McNichol, Frank Blunstone, Derek Saunders, Jim Lewis and Peter Sillett  Within three years, in the 1954-55 season, Drake had led Chelsea to their first league championship triumph. In doing so, he became the first person to win the league title both as player and manager. However, Drake never came close to repeating the success. The championship-winning side was gradually broken up, to be replaced by the crop of youngsters emerging from the club's youth team, such as Jimmy Greaves, Peter Brabrook and Bobby Tambling, for whom Drake was an aloof figure. Thereafter performances and results were very erratic, leaving the club stranded in mid-table; an FA Cup loss to Fourth Division side Crewe Alexandra weakened his position at the club and a few months later, Drake was sacked early into the 1961-62 season.  After leaving Chelsea, he became reserve team manager at Fulham. During 1970 Drake went on to have a six-month stint as assistant manager at Barcelona. He later returned to Fulham where he became a chief scout, director and life president of the Cottagers. Drake passed away at the age of 82 on 30 May 1995.

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He discarded the club's Chelsea pensioner crest and with it the Pensioners nickname, and insisted a new one be adopted.