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Why the bootstrap fails on an extreme tail quantile

A risk team wants a confidence interval for the 99.9% Value-at-Risk of a portfolio, an extreme lower-tail quantile, from a few thousand daily returns. They bootstrap: resample the returns with replacement, recompute the 99.9%99.9\% VaR each time, and take the percentile interval. It comes out surprisingly narrow.

Explain why the ordinary bootstrap is unreliable for this statistic and what resampling or modeling approaches are more trustworthy.

Your answer

This one is open-ended. Work it through, then check your reasoning against the full solution.

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