Several years ago the Grandmaster, an Elder of the Universe and cosmic gamesman, had traveled to the alternate reality of the Squadron Supreme (Earth-712) where he challenged the Scarlet Centurion to a contest of champions. The Grandmaster picked the Squadron while the Centurion picked the Institute Of Evil as his champions, and the Squadron emerged triumphant giving the Grandmaster a victory. The Grandmaster then traveled back to the prime Earth (Earth-616) where he sought out Kang The Conqueror. The Grandmaster challenged Kang to a similar contest. Kang chose the Avengers as his champions, but the Grandmaster decided to create his own. He modeled his pawns after four members of the Squadron Supreme. He gave James Saunders a chemical formula to grant himself super speed, and he became the Whizzer. The Grandmaster drafted the recently turned superhuman Kyle Richmond and called him the Nighthawk. He gave the power prism to Dr. Kinji Obatu who became Doctor Spectrum. To round out his team the Grandmaster created the Superhuman Hyperion from nothing. After gathering his pawns together he named them the Squadron Sinister and sent them to fight the Avengers. The Avengers won the battle, and the Grandmaster abandoned the Squadron Sinister and the group disbanded.
Recently, the Grandmaster has reformed and increased the powers of the Squadron Sinister with the Speed Demon, a new Doctor Spectrum, and an apparently resurrected Hyperion. Nighthawk declined to re-join the Squadron, and joined the Thunderbolts until he learned the only reason Songbird asked him to join was for his money, he quit and joined the Squadron Sinister to help defeat Baron Zemo and the Thunderbolts.