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Tax Alpha Insider

Tax-aware long/short: integrated to overlay via Section 351

Long position cost basis is a finite resource

Brent Sullivan's avatar
Brent Sullivan
Mar 17, 2026
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FYI: The Tax-Aware Long/Short Working Group will meet on Day 2 of Basis Northwest.


📺 🔴 I’m doing a webinar w/ Burney Advisory Services about tax-aware long/short.

When? March 18, 2026, 1:00 pm ET (i.e., tomorrow).

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An ossified portfolio could be “reinvigorated” using long and short extensions and again using Section 351 conversion

A long position’s cost basis is a finite resource.

So, it’s possible that after a handful of years, tax-loss harvesting potential has been completely exhausted.

Many folks call this “portfolio lock up,” or my favorite… “portfolio ossification.”

For a long-only portfolio, there are various solutions, including injecting cash, adding long/short extensions, gifting low-basis shares, and contributing the entire portfolio to a specific type of partnership (similar to, though not the same as, an exchange fund).

Ok, so suppose you’ve decided to go the long/short route…

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