Green’s Dictionary of Slang

an itinerant rural confidence trickster who travels in search of new victims for his cheating skills; thus crossroad, v.

1897		Eldridge & Watts Our Rival, the Rascal 193: Of late years a frequent substitute for the ordinary ‘gold brick’ game has been played by swindlers who are technically known as ‘cross-roaders’.
1961		J. Scarne Complete Guide to Gambling 676: crossroader A card cheat who travels over the country seeking card games in which he can ply his trade.
1966		M. Braly It’s Cold Out There (2005) 193: I been a tramp and a crossroader [...] since the day i slipped out of the barn.
1981		E. Bunker Little Boy Blue (1995) 84: Abe had been a professional thief, booster, and con man, one who crossroaded around the country.
2003		St Petersburg Times (FL) 17 Apr. 🌐 ‘This is cheating,’ he says, launching into a demonstration of how a band of ‘crossroaders’ (cheaters, in gambling parlance) managed to bilk a South African casino out of $30-million by concealing high-value chips inside hollowed-out stacks. [...] . Since the day in 1987 he saw a crossroader muck his cards at a high-stakes blackjack table, swapping a winning pair for the cards he was dealt, Swain has been as fascinated by the technical skill of cheating.