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Could someone buy one of these negative bonds in hopes to short sell it? I barely understand shorting, but it seems like this would be an opportunity (I realize shorting is always risky).

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Shorting means borrowing the asset from someone else and selling it, not buying then selling.

I'd guess shorting isn't allowed but could be wrong. It certainly should be allowed.

There are secondary markets for most bonds so yes, you can short them. However most traders would do this through derivatives such as bond futures or ETFs.

Most traders would pick the optimal instrument to express their view which could end up being bond futures or ETFs but not always.

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