Despite the wonderful and fantastic things that he has done in his lifetime, Anthony Masters' origins are rather common and depressingly ordinary. Born in 1898 in a bordello in the Bronx, Anthony was just another street urchin for the longest time. He had more mothers than he knew what to do with, even after his biological mother passed on from tuberculosis when he was only six. Anthony has very little remaining memories of her, though he does remember a strong, if tired woman of young years. Sometimes he sees her sea blue eyes in his sleep, as if she is still watching over him.

Never knowing who his father was, and with no other blood family to watch out for him, the charity of the Madame and his other "mothers" ran out when he was only ten years old. So Anthony did the only thing a young man could do in such times and circumstances: he joined a motley band of street children. For years, pick-pocketing was the only thing he could do to keep food in his belly, even if he rarely had a roof over his head. It wasn't a glamorous life, but it was his life. The one advantage he had over the other kids was that he could read. The kindly women that had helped raised him had made sure to give him basic schooling, even if he never had an official education.

This allowed Anthony to escape the poverty and hunger from time to time by visiting the public libraries, or stealing pulp magazines from the news stands. It was within the pages of novels and magazines that his desire for adventure was born. Unknown places, far from the filthy streets that he grew up on. Places of wealth, women, and wonder. And though he was nothing more than a pickpocket with visions of glory, he struck upon an idea. Though he was only sixteen years old at the time, he went to the New York French Embassy, and applied to join the French Foreign Legion. He chose the surname "Masters" after Edgar Lee Masters, a attorney, poet, biographer, and dramatist that he had read throughout his childhood.

Assigned to the 7th Algerian Tirailleurs Regiment, Anthony was shipped off to Africa as part of the larger Armée d’Afrique. Not aware of the larger events of the world, he was surprised that only a few short months after his recruitment and training, the Great War broke out. For four long years, Anthony fought in that hellish war, with engagements all over Africa and Europe. He gained and lost dozens of friends, and learned things on the battlefield that no man should have too. But it was to such a terrible environment that Anthony thrived. War was something he excelled at, and the bloody fields of Europe, and the sands of Africa provided all the excitement and travel that his childhood and then some. And he seemed to pick up complex tasks and abilities just as easy as the other soldiers could breathe. He was able to match the marksmanship abilities of Francis Pegahmagabow after only watching him snipe for a day. He was able to fully match the peerless saber-fighting skills of Charles Hornby after only an afternoon of watching him train. A brief mission with Colonel Thomas Edward Lawrence allowed him to be every bit the pistolier and knife fighter that legendary commander was. But after the War, the hardened soldier found that he had little to do.

Leaving the French Foreign Legion, Anthony tried to find his own fortune and glory, without a flag to fight beneath. With more expertise in Africa than Europe, he initially took to leading wealthy Europeans on expeditions into the "Dark Continent," and guarding archeologists during their explorations. He developed a taste for the exploration, but found the company insufferable. His brief contact with the country of Wakanda convinced him that the assumptions of the European academics about cultural and technological development was wrong. Abandoning his career as an explorer after only three years, Anthony thought perhaps he could find worthy causes to fight for as an independent operator. Taking commissions from the north African governments, Anthony fought against the widespread slave trade that had taken root in the aftermath of the war. All over north Africa and into the Middle East, Anthony took on ruthless men, and made his fortune in both payment, and "liberated" plunder.

He might have gone on like that indefinitely, had not been for a chance meeting with the legendary ninja Ogun in the city of Madripoor. Despite his great fighting skills, Anthony was handily defeated by the great warrior. It was then he learned that the abilities he had learned from Bob Scanlon were not enough. Vowing to never be defeated again, Anthony took to searching out the greatest martial arts masters from all over Asia. With his Photographic Reflexes, he was able to absorb decades of study quickly, before moving on to learn from the next master. Of all of them, Anthony has to to admit the Hand were the most deadly, and most dangerous.

But after all these years of war, travel, and training, Anthony started to feel homesick for the land of his birth. He had been gone from America longer than he had lived there as a child. Armed with all the skills from war and the far East, Anthony decided that he might ply his trade as a mercenary in the greatest city on Earth. But America isn't the kind of place that respects warriors and soldiers like in other parts of the world. Here, one can only truly be themselves beneath a mask. Hence, Anthony has taken up the moniker of "Taskmaster," and wearing a skull-mask to obscure his identity. A bit theatrical maybe, but the mobsters and politicians that make up New York's elite seem to love it.