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Fleming is a former Lieutenant in the Royal Army and served as head of the Royal Secret Service following the death of his immediate superior and old comrade, Ian St. John. Fleming is close to Ian's only son, Geoffrey St. John, and became the father-figure and mentor to him that he now lacked. Fleming is also a close friend and old comrade of Commander Smiley.
Fight against Overlanders
Fleming was a lieutenant in the Royal Army under Smiley's command during the Great War. When Mobotropolis came under mortar attack from enemy shelling they successfully managed to defeat the Overlanders in an ambush lead by Bernadette Hedgehog and Cocoa that injured Amadeus Prower and cost him his left eye. (StH: #76)
Rebel Underground and Retirement
Fleming served well during his time as head of the Secret Service, but later joined the Royal Underground along with Smiley under Geoffrey St. John following Dr. Ivo Robotnik's coup in order to restore the realm. As a member of the Rebel Underground, Fleming helped Sally's trainees during one of their early missions, by locating and helping to heal the injured Arlo. Both he and Smiley later participated in an attack on the last energy substation of Robotropolis's defense grid and helped to defeat Robotnik's Stealth Bots. During Operation: EndGame, both he and Smiley handled Tasmanian Devils that were used to track down the escaped convict, Sonic. After Robotnik's death, Fleming and the rest of the Underground joined up with the the Knothole Freedom Fighters to restore their decrepit capital of Mobotropolis. He later transported the crystalized Kodos and Uma Arachnis to the Devil's Gulag, explaining how they had gotten in that condition to Smiley. (StH: #48, #49, #50, #54 SSS: #2, #6, PSM: #3)
During a routine sweep-and-clear mission to destroy booby traps laid by Robotnik before his demise, Fleming accidentally tripped a landmine that nearly got himself and Geoffrey killed. While they both lived, Fleming, injured, realized that he was "too old for this game" and retired from active duty, letting Geoffrey became leader of the reformed Secret Service. Fleming was also sent to Devil's Gulag with Smiley as one of the guards their but he like the rest of the guards were serverly injured by the escaped convicts but was saved by the help of Dr. Quack. (StH: #61, #63, #69)
- Fleming and Smiley in the early issues did not have their beaver tails and so were confirmed as chipmunks but this was changed in the later issues.
- Fleming mustache is changed to brown instead of white in the earlier issues.