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This comes from the movie "Black MASS". (FBI Agent asking): "From what were you and Mr. Bulger making your money?" (prisoner) : "Ah.. It was a lot of things.. Running dope on the streets of Southie. We had the rackets. We had the ponies. Tenants on every corner. But we were making weekly collections...You name it, and yeah, we was doing it...".

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    Farlex Dictionary of Idioms lists the fixed expression 'play the ponies'; 'ponies' thus obviously refers to racehorses / horse racing in general. 'Tenant' must be a broadened sense used in criminal argot; I can't find a dictionary reference.
    – Edwin Ashworth
    Commented Aug 6 at 11:40
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    You should probably note that Whitey Bulger was from near Boston, USA, and so any argot is probably Boston area criminal slang.
    – Stuart F
    Commented Aug 6 at 11:44
  • ponies refers to horse racing here. This guy's brother was a university administrator in MA and probably suffered a lot due to his criminal brother. What an ass he was. And murderous.
    – Lambie
    Commented Aug 6 at 14:39
  • Surprised you didn't ask about "Southie" - that very specifically is a nickname for South Boston en.wikipedia.org/wiki/South_Boston. I've never heard "Southie" used by any other city (not that it couldn't be, of course).
    – James Moore
    Commented Aug 6 at 21:42

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  1. "The ponies" is slang for horse racing.
  2. Tenants can be someone who has to pay the criminals for being able to work in the area. This can be drug dealers or prostitutes who have to pay a cut of their earnings or it can be a protection racket of local businesses.
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    Tenants may refer to the “protection” racket—criminals extort payments from otherwise law-abiding businesses for the privilege of not suffering violence. Compare to the line from the Genesis song The Battle of Epping Forest: “Now, after working hard in security trade, he's got it made. // The shops that need aid are those that haven't paid.”
    – PaulTanenbaum
    Commented Aug 6 at 12:58
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    And in this context 'the ponies' means taking bets on horse racing, aka bookmaking, which until recently was illegal in MA but popular and thus a lucrative business for organized crime
    – dave_thompson_085
    Commented Aug 6 at 19:30

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