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Loophole

Upstream Basis Planning

Gift appreciated assets to parents, inherit back stepped-up.

Overview

Gift highly appreciated assets to an elderly parent with a small estate. On their death, assets pass back to you (via their will or trust) with a full §1014 step-up in basis — eliminating built-in capital gains. Requires parent survives >1 year (§1014(e) anti-abuse rule) and coordination with their estate plan. Powerful when parents have unused exemption.

Best fit
Owners of highly appreciated stock/REAdult children of elderly parentsLow-basis concentrated positions
Estimated impact
Eliminate 20–37% cap gains on entire appreciation

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