A figure of the con-man tradition at its most organized, Smith ran criminal enterprises across the frontier West that went well beyond simple grift — he effectively controlled the underworld economies of entire boom towns. His gift was institutional: using early rackets to fund increasingly elaborate operations, he built a succession of criminal fiefdoms that blended fraud, political influence, and muscle. The gold rush brought him his largest stage in Skagway, Alaska, where he ran the town until a vigilante confrontation ended his career at thirty-seven.

His career traces a durable arc through organized crime's upper tiers — from heroin distribution in partnership with Nicky Barnes in the 1960s and 70s, through repeated imprisonment and return, to eventual leadership of the Lucchese family as acting boss. What makes him a notable entry here is less any single act than the breadth and persistence of it: illegal gambling operations measured in the billions, loansharking, extortion, corruption of city inspectors, and ultimately a murder conviction that ended with a life sentence. He was inducted into the family specifically as a reward for staying silent under grand jury pressure, a detail that illuminates how the institution valued and sustained itself.

Colston's career illustrates how the infrastructure of the transatlantic slave trade was embedded in the commercial and civic life of respectable English society. As a senior figure in the Royal African Company during its peak years, he was directly involved in an operation that transported an estimated 84,000 enslaved Africans, of whom roughly 19,000 died during the crossing. His simultaneous role as a prominent philanthropist — endowing schools and almshouses in Bristol and London — allowed his reputation to be carefully curated across centuries, a dynamic that made the 2020 toppling of his statue as much a confrontation with that legacy as with the man himself.