Born in 2211, Gergenstein was a bit of a nerd and a science geek as a child, ostracized by his peers for being smart and different. When his mage powers manifested at puberty, he frequently got into trouble for using them against his classmates and tormentors. He was drafted into the Tech Infantry at 16, but quickly sent to OCS when his intelligence and drive were recognized.
While at OCS, he was recruited by Rashid King to join Internal Security and become a mole in the ranks of the regular military, spying on our own troops to ensure their loyalty. However, surrounded by other supernatural creatures who could literally read his mind, such a task was a difficult one, and he was eventually exposed. He was transferred instead to perform the same role in Earth Fleet, with his personnel file altered to make it seem as if he washed out of Tech Infantry boot camp for being an unusually weak mage unsuitable for ground combat, but still needing to serve in the military to earn his citizenship. He continued in this role for several years, eventually serving as Sensor Officer on board the EFS Schaumburg under Captain Erich Von Shrakenberg.
Gergenstein had been groomed for many years as a protegé of Rashid King to be his possible successor. Returning to non-covert Internal Security service after the EFS Schaumburg was laid up for repairs following the Battle of Rios, he took over the organization after the death of Rashid King during an attempted coup in the middle of the Battle of Avalon. After the rise of Arthur Clarke to power, Gergenstein and most of the rest of his faction in the government and military were forced to flee into hiding.
After decades in hiding, Herbert used the remnant of the Internal Security apparatus to continue their activities and grow their network. When Clarke finally died, he offered his services to the new head of the Earth Federation, Joseph Smythe. Having limited resources himself, the admiral jumped at the chance and promoted Gergenstein to an Earth Fleet Captain, and head of his spy service.
Athough he was successful in allying the Earth Federation with theMinistry of Public Safety and the Sabbat, after the Battle of theRound Table, he realized the Fed's days were numbered. He arranged to have Smythe and his mother killed, cashiered the Tech Infantry to disband them, and became the new leader of the Imperial house, Vendo.
After the Federation was conquered by the Eastern Bloc and the Middle Kingdom was established, Gergenstein used InSec's contacts with the yakuza and the patronage of Andrea Treschi (a former InSec officer who has become the Left Minister to the Celestial Emperor) to transform the remains of InSec into Yakuza-Gaijin, the only known non-han crime family. Treschi gained a secret, unoffical spy service and black ops team, and Yakuza-Gaijin gained legal protection at the highest levels of government.
Herbert Gergenstein is named for "Herb", a nerdy character in a Burger King ad campaign from the 1980's, and for a backward spelling of Greg, the name of one of Martin's childhood friends. His middle name came out of a typo - storyteller Marcus Johnston accidentally refered to the character as "Wilhelm" early in season 4.3, and the error was retroactively explained away as Gergenstein's middle name. The name was first used by Martin for a character in an award-winning time-travel story he wrote in seventh grade, and recycled for a quite different character in TI. Originally he was supposed to have tried to evade the draft and thus have a few Resistance contacts, but the plot where that fact could be made use of was scrapped early on, and Marcus changed his backstory to create a replacement supervillain once Rashid King went down. His Actor Avatar is John Cusack, chosen by Frank for a parody he wrote.