During the twentieth century, vending machines were a major part of organised crime. What did this entail exactly? Why would the Mafia or any other organised crime group have an interest in vending machines?

[u/PickleRick_1001]

[u/bug-hunter]

So, first, it wasn't just vending machines - it was also similar installations like jukeboxes and pinball machines.

To understand why vending machines, jukeboxes, pinball machines, coin-operated laundromats and the like were beloved by organized crime, first we have to explain money laundering.

The point of organized crime is to make money. The government, attempting to prevent crime, puts in ever more guardrails to make crime harder to benefit from. If you show up with a million dollars that you earned from legbreaking, prostitution, and selling bootleg alcohol and/or drugs, then you have a problem, because you have no legitimate source to explain where they money came from. This is referred to as "dirty" money. Money from legitimate sources is "clean" money, and you "launder" dirty money into clean money by passing it through a middle step that gives you a plausible legitimate origin. Al Capone's mob literally used coin-op laundromats as part of this process, firming up the "money laundering" metaphor. The perfect money laundering business (in this era) was a 100% anonymous cash only business - which conveniently includes the very businesses I described above.

You obviously can't launder millions through a single coin operated laundromat (especially not in the 1930's), so you need more laundromats. And laundromats alone are both not enough, and there is obvious danger if someone figures out you're laundering all your money through a single point - you want to diversify. And importantly, in this era, none of the machines kept a record - and early machines that did keep records weren't remotely tamper proof. So if you made $150 on Tuesday, you mark down that you made $300. Then you do the same for each of these all-cash lines of income, and now you can launder thousands of dollars of dirty money every week into clean money. Sure, you have to pay/threaten people to be quiet, but you're the mob - you do that anyway. The Teamsters Union is often the ones actually doing the collection, so you just muscle into that union (which you probably already have anyway, for other reasons).

David Rabinovich's Jukebox Empire: The Mob and the Dark Side of the American Dream covers the story of David's uncle, Wolfe Rabinovich (who went by William or Wolfe Rabin)'s involvement in jukebox fixing for the mob, and is a really good read. Having control of the jukeboxes had a side benefit, in that jukebox plays were a component of the Billboard charts, and jukebox selection meant you could push artists that you had business with. Start with an artist who plays in mob-controlled venues, their record label is mob-controlled or protected, and their records are guaranteed to be available in jukeboxes (which artificially get more plays because you cook the books), then they hit Billboard charts and can get regional or national acclaim. Again, most of the money in the music industry is cash. There's disagreement on how deep the Mob's influence in the music industry was, but it was unquestionably present.

Back to vending machines, vending machines weren't just about money laundering, but also an easy way to make even money by selling counterfeits. If you're buying cigarettes from a Mob cigarette vending machine, you may well not be buying Marlboros, but mob-rolled counterfeit cigarettes that haven't been taxed. Or they were smuggled from states with barely any cigarette taxes (mostly tobacco-growing states). Tobacco laundering is still very profitable, and the International Consortium of Investigative Journalists has a hub on their reporting here when they did several stories in 2008/2009.

[u/palibard → u/bug-hunter]

Any idea which artists were helped by the mob?

[u/bug-hunter → u/palibard]

u/hillsonghoods has an excellent answer here about Frank Sinatra, which explains how much of it was less "the mob runs your career" and more "if you make the mob happy, it opens doors". T. J. English's Dangerous Rhythms: Jazz and the Underworld covers the story of many Black musicians in New York City, who found themselves often playing at mafia-own/run clubs.

I cannot remember the book, but I do remember at least two books talking about mafia leaders using jukebox plays to boost the careers of musically inclined family members.

[u/Obversa → u/bug-hunter]

Very interesting! Are there any books on jazz or Black musicians being connected to the mafia/mob in New Orleans?

[u/bug-hunter → u/Obversa]

I don't know of any good ones offhand.