Maverick
The Maverick boys - Bret, Bart, Beau and Brent - are a clan of well-dressed dandies, gamblers who'd much rather make their money playing cards than messing up their fine clothing with actual work. Sly and clever, none of the Mavericks are much for acts of derring do, but they can be courageous when the situation calls for it. Most often, however, they live by their wits and considerable charm.

Season 2 · Episode 8 ·
The Jail at Junction Flats
Good-hearted Bret lends a pal $200 for an ""honest"" transaction — which lands the pal in jail.
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Episode 8 of season 2 of Maverick: “The Jail at Junction Flats”. Aired 1958-11-09. Watch it online free on ZapFlix.