Backgammon money play generally takes one of several standardized forms.
Private clubs will usually have a regular chouette going several days a week. At the old Ace-Point Club in New York in the 1990s, for instance, a $25 chouette would start around 3 to 4 p.m. and continue until past midnight. Usually these games have a few regulars and a rotating crew of occasional players.
The game used to start with as few as three players and get up to 6 to 8 players in the evenings, tapering off at late night. By the end of the evening, the big winner might be up $1k to $2k or more, with the big loser in the same range. That game went on pretty much 7 days a week for years.
A club might have multiple chouettes going at different price points. The Ace Point also used to have an occasional $100 game (Phil Laak was a regular there I recall) and a $5 game.
At tournaments, there will be chouettes in the evening after the tournament games are finished. $50 a point is a typical stake. During the 1990s, all the big tournaments had an ongoing $200 chouette with a regular cast of characters. The big winner in the chouette would pocket far more than the winner of the actual tournament.
At tournaments players might play the occasional heads-up session, which would usually be limited to 10 or 20 games, agreed to in advance. Stakes could be anything.
If an interesting position arises, a prop (proposition) may form, with the players betting on which side has the better of it. Usually players would contract for a set number of games, like 50 or 100.
One of the best is "Double 1s versus the cube". You ask your opponent "Would you rather start a game with double-aces, or owning the cube?" Whatever answer he gives, you offer to take the other side. If he's confident of his choice, he'll probably be willing to play for more than $4/point.
(In fact, doubles 1s is slightly favored in this prop, but it's close. The whole idea is to get something going where your skill can tell, and the way to do that is by letting your opponent think he's getting the better of it.)
Another idea is to just play until you see your opponent make a cube decision that looks like a big blunder. After the game, offer to play it as a prop. Since the position came up naturally, and since he's already tied his ego into the wrong choice, you should have an easier time getting a prop started.
Bots have affected things in the sense that props are always settled on the spot, before anyone has had a chance to do a Snowie rollout. Sometimes players will just skip the actual play and wager on the result of a rollout of such-and-such a ply level and so many games.
As you can see, the heads-up backgammon session is actually somewhat rare. The backgammon money scene is really dominated by chouettes. They're a lot more fun and, for good players, more profitable as well.
Next article: A History of Backgammon's Popularity