The first Rick Flag led a small squadron of men in World War 2 called the Suicide Squadron. It was a disaster as only Flag survived the first mission the rest of the members died, with this Flag's success increased but at a price of his mortality. Soon after World War 2 Flag married Sharon Race and a few years later when the Justice Society of America disappeared Flag was called into Task Force X by the President. The Task Force X had two divisions: Argent (which dealt with civilian matter) and masked villains, the second division dealt with national crisis. In the end Flag sacrificed himself to stop an old Blackhawk nemesis called the War Wheel, however he did leave a son behind, Rick Flag Jr.
Rick Flag Jr
After the first Rick Flag's death he was replaced by his now grown up son, Rick Flag Jr who was leader of a public team but one mission in Cambodia went horribly wrong as his team was pursued by a Yeti. Two members of the team along with the yeti fell into a crevice. One survived bitter and angry for being left behind by his teammates. That man survived his life saved by the Chinese and healed by them, and soon after was transformed into the cyborg Koshchei the Deathless. Rick's
girlfriend also secretly had his son giving him up for adoption far before Flag even had an idea. Flag worked covertly until being placed in a new squad, formed by Amanda Waller which much to his dismay he resumed. He loathed working along with former criminals and killers such as Deadshot and refused being alike with them in any way whatsoever.
It was revealed that other Squad member Nightshade had feelings for him but it was never revealed to Flag. Flag also befriended Squad members Nemesis and Bronze Tiger, the whole relationship inside the squad was a complicated mess but loyalty was no object as the missions continued. In a terrible mission with a different squad all members but Flag were killed thus causing Senator Clay to threaten to reveal the Suicide Squads existence thus causing Flag to go on a mission of his own to kill the senator although in the end it was Deadshot who shot and killed the Senator and the Squad's existence became public knowledge.
During a mission Rick Flag set off a nuclear bomb in a Jihad stronghold, the result of the explosion: his death but this was not the end for Flag.
One Year Later
One Year Later Rick Flag is revealed to be alive (not the result of the "retcon punch", simply his own skill) and rescued by Bronze Tiger from a secret Quarci prison after imprisonment for 4 whole years until Amanda Waller learned he was still good and well and had Tiger break him out. Later on in his epic adventure of a life Flag is transported to Skartaris with old friend turned enemy Rustam after killing Rustam and returning home it is revealed that the man who thought he was Rick Flag Jr. is really a soldier named Anthony Miller who was brain washed by Wade Eiling into believing he is Rick Flag Jr. After getting rid of the implant that was keeping him brain washed Miller stays on the Squad as Rick Flag commenting that it will always need a Rick Flag.
Rick Flag III
Rick Flag's son was revealed again in a Suicide Squad comic where Flag is too scared to approach the child.
In Other Media
Flagg recruited four outlaws into a group named Task Force X, under the directive of Project Cadmus. Their covert mission consisted in infiltrating the Justice League's headquarters to retrieve the Annihilator. While Deadshot and Plastique created a distraction, Flagg and Boomerang rushed to the armory. When they were intercepted by three Leaguers, Flagg took on Vigilante and Shining Knight single-handedly in hand-to-hand combat. Thanks to his dexterity, the mission was a success.
Unlike the others, Colonel Flagg, Jr. wasn't blackmailed into going on this suicide mission—he did it out of patriotism.
Rick was among the the members of a mysterious group that attacked and abducted Oliver Queen at the satellite station. He interrogated and tortured Oliver for information about his team and his involvement in the recent alien attack. He later released Oliver, but warned him that he wasn't through with him yet, and traded him for another hostage, Chloe Sullivan.
Rick had Plastique and Deadshot track the heroes, as he encountered Oliver who was searching for Chloe. After getting into a fight with Oliver, in which he grazed him with a bullet, tagging him with the mark of the Suicide Squad, He told Oliver that she had killed herself by ingesting cyanide pills. He and Plastique later broke Deadshot out of prison.
Rick Flag targeted General Sam Lane for his support and contribution for the vigilante registration law. He aims to eliminate those who would force heroes and super-powered people to come out of hiding. Later to justify his assassination attempt on the general (he fired a missile that was meant to eliminate Sam Lane and those in his company), he said he did so to keep the Act from being passed, however it almost killed Lois Lane, had it not been for the Blur saving her and showing General Lane that some heroes like the Blur need to be "in the shadows". With the Act had finally passed, Flag was forced to make his move by having his Squad members take down Anti-Vigilante support areas.
Rick Flag and Suicide Squad member, Deadshot, joined forces with Chloe Sullivan to save the Justice League from the VRA's abduction and experimenting of their special abilities. It was revealed that Chloe had threatened to turn him over to the government after his attempt to murder General Lane in exchange that him and his squad follow her orders.