I don't understand blackjack (longish)

[MCS]

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Can you really say that $5 is the expected loss on a $1,000 bet?

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If he knows how to play, he's right that the edge is small (let's not nit this up by arguing about precise numbers or assumptions or the effect of different rules, it's still small and $5 is a reasonable claim). His risk of "ruin" is high but so is his chance of robusto.

However, it does sound like he's betting really big and drinking a lot, which is a terrible combination. I suspect he is not playing well and is betting more than is healthy, and I would be concerned this will escalate.