I don't understand blackjack (longish)

[SheetWise]

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However, Blackjack is a game of high variance, and it seems as though your buddy is betting 20%+ of his starting bankroll on some bets, which greatly increases his risk of ruin.

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A "starting bankroll" in blackjack doesn't really have a lot of meaning since you can play out of pocket -- but you're certainly right if he meant to limit his bankroll to $2,000. To be somewhat certain of being able to continue play to "expectation", about 100 top bets would give you some comfort. If he considers a $5 loss per $1000 entertainment fees, he's still paying $40-$50 an hour playing $100 a hand on a full table.

It's not a terrible play for someone who wants to take a quick shot and get some real action -- because you almost always do.