Lionel Geoffrey Tiptoft is the son of Susannah Johnson and Frederick Evelyn Tiptoft, who styles himself the 28th Earl of Kingston-upon-Quick — thus rendering Leo the 29th in the line, assuming it actually exists. Most Virgan experts regard his father as having an illegitimate claim on the peerage, although he represents such an insignificant branch of the Virgan aristocracy that nobody really much cares. Indeed, the Tiptofts aren't even rich: Susannah is a stay-at-home mother who's helped raise five children (of whom Leo is the oldest), while Frederick runs one of the several thousand auto repair shops in Kingston City.
Like so many working-class kids in Virgon's industrial center, Leo's childhood was marred by occasional brushes with the law — for vandalism, underage drinking, traffic violations, and so on. When he wasn't skipping class or tooling about Kingston's cramped streets on his custom motorbike (a vintage Areion VX-300 he nicked from a junkyard and repaired himself), he could usually be found on the Pyramid court taking on all comers. With a deadly array of spins, trick shots, and power moves, Leo caught the eye of a promoter named Archie Devine, who paid him a modest sum to appear in street-ball matches alongside other promising young talents.
At roughly the same time, Kingston State College — the local public university — began a concerted effort to improve its Pyramid squad after a generous anonymous donation. KSC built a new stadium, hired an all-star coach, and began aggressively recruiting at the usual litany of top prep schools. But breaking with tradition, Coach Liam Shireson also dispatched scouts to the street games run out of rusted playgrounds and makeshift courts, hoping to find a diamond in the rough. And when he got word of a transcendent talent wrecking shop just thirty-five miles from his school, he showed up to one of Tiptoft's games — just in time to see him drop six points on the hapless Third Street Crew in a single quarter. Shireson offered Tiptoft an athletic scholarship on the spot, and the young man — to whom Pyramid was a religion — eagerly accepted.
It was a prescient move. With Tiptoft leading the charge, KSU's underrated team managed a .500 record in the brutal Northern Virgon Conference, including a stunning overtime victory over tenth-ranked Astraia University to close out the season. The next year, the Mustangs took second in the twenty-team NVC, losing the title on a controversial excessive celebration call on Tiptoft himself. And as a junior, Tiptoft set conference records for scoring and range en route to a career-high eight-point game against the reigning Themis Wolverines to clinch the NVC title. Though fifth-ranked KSU ultimately fell in the Quantum Communications Bowl to fourth-ranked Picon U, Leo's performance solidified his stock as one of the best college players in the business.
Rather than return for his senior year, Tiptoft declared for the draft and was selected in the first round by the Gemenon Twins, traditional bottom-feeders in the professional league. Though he was a middling defender, Leo's brand of flashy offense rejuvenated the team's flagging fanbase. But three-quarters of the way through his first season, one up until that point destined to win him Rookie of the Year, the Delphi Herald-Tribune reported that the Twins were being investigated for abuse of performance-enhancing substances: and that Tiptoft was among eight players facing a two-year ban from the sport.
Leo fought the decision with every resource at his disposal, throwing his newfound millions at a team of attorneys and PR men in the vain hope of overcoming the charges. But the Commissioner held his ground, and the Gemenese media soon turned against the mercurial rookie when reports of his off-the-field activities came to light: lap dances at Virgan strip clubs, five-thousand-cubit meals at top restaurants, and the like. Eventually, an arbitral panel upheld the Commissioner's ban. Just like that, his promising career was over.
Tiptoft returned to Virgon as broke as when he left it. He spent the next few months tooling about the city streets on his old VX-300 and taking odd construction jobs on the side. His circle of friends evaporated almost as quickly as it took for his collection of girlfriends to vanish — and soon, he faced the prospect of working in his father's shop for the rest of his life. With new purpose, he buckled down, finished his degree in Marketing at Manifold Community College, and joined the rest of his cohort of young, restless men in the Colonial Fleet.
Leo graduated from Basic Flight in the top ten percent of his class and was assigned to the Viper pipeline, where he learned to deploy his natural hand-eye coordination to deadlier ends. Upon receiving his commission, he spent the first two years of his career with VFA-8 ("Ragin' Rams") aboard Battlestar Solaria (BS-88) before being transferred to VF-777 upon receiving his promotion to JG.