Bradford comes from a clan of dairy farmers, hence their choice of the name 'Milkman' when the surname law was enacted in 904.
Bradford had a brother named Chazz, who was six years older then he. When Chazz turned 13, in 894, he joined a local gang called the Victors, which at the time was led by a young man named Kane. Two years later, a 24-year-old woman named Larami joined the gang as a spy, the same job held by Chazz and several others. The chief spy at the time was a 19-year-old boy named Zada, who'd been in the gang for seven years. A few months after Larami joined the Victors, when Zada turned 20, he quit the gang to find a real job. Though Larami was the gang's newest recruit, she was the oldest of the gang's spies, and she had quickly become as good at the job as anyone. So, she became the new chief spy. Three years after that, in 899, Kane retired, and Larami became the new leader. Over the past few years, she'd come to respect Chazz (who was now 18) more than any of the other spies in the gang, and made him her new chief spy.
It was that year that Bradford turned 12, and he hoped to follow in his big brother's footsteps, by joining the gang as a spy, himself. However, now that Larami was in charge, she planned to change the gang into a more serious enterprise, employing only adults. Coincidentally, that was also the year that gangs around the world started becoming more serious, rather than a childhood rite of passage, as they'd always been before. And it wasn't long after Larami become leader that she became one of the founding members of InterGang. So, Bradford wasn't allowed to join the Victors, nor any other gang.
When the new school system was implemented in 904, Bradford enrolled in tenth grade. One of his best friends there was Porter Cognoscente, who was a year older than he. The two had known each other for years before that, but only vaguely. Porter's father owned the Apple-Spruce Inn, which was one of many businesses to which Bradford's family made milk deliveries. While Bradford and Porter had met in that capacity, they'd never really socialized until both entered school. The next year, Bradford began attending Tonad University, but Porter took a year off from school, not starting university until 906. The two of them reconnected, though Bradford was now a sophomore and Porter just a freshman. Later that same year, Porter organized a small gang called the Brills, and Bradford was one of its first members. So he finally got to be in a gang, just like Chazz. Some time after that, Porter became somewhat friendly with Larami, and their visits allowed Chazz and Bradford to spend some time together, which they'd rarely done in the years since InterGang was founded. Their parents had never minded the idea of Chazz being in the Victors as a teenager, but InterGang was different; it was a genuinely criminal organization. So, Chazz's decision to remain in the gang had led to his parents severing contact with him, and Bradford had had no choice but to go along with their wishes, as much as he didn't want to. The brothers were glad to see each other again, and Chazz introduced Bradford to Larami.
In 909, Chazz was killed by enforcers from LandOrder, and subsequently, a deal was struck by which Porter released Bradford from his service to the Brills, so that Larami could hire him to replace his older brother as her chief spy. Though Larami hadn't known him long, she'd come to respect his abilities as much as she had respected his brother's. Bradford had also become known to the spies under Chazz's command, so there was little or no objection to his being hired, instead of one of InterGang's own spies being promoted. Bradford quickly became one of Larami's most trusted employees, and in 912, he helped her plan and implement her defection from InterGang to found her own intervillage gang, the Illuminati, of which Bradford became First Spy. It was also at that time that the Brills joined the Illuminati, with Porter becoming don of the new gang's Tonad branch. So, the two old friends would once again get to work closely together on the same team.