Personal Investments • Liquidate small STCG, or larger LTCG first?

Howdy,

Retired. Need to sell some assets early next year. I have:

• One large block of VTSAX - STCG - 5% gains
• Several small blocks of VTMGX - LTCG - 43% gains

I am wondering which one is better to sell (ignoring concern of asset allocation - I can fix that elsewhere). One possible wrinkle is that I have two large shares of private equity stock, either of which could be sold/IPO'd next year and might trigger a large windfall that would influence how these sales are taxed.

I think the answer is:

• if both have a gain, sell the VTMGX because capital gains tax will be 0 (up to $47,000 in gains)
• if there is a market dip such that the VTSAX shares go to 0% or negative, sell the VTSAX

I am a little less clear on the scenario where I end up with the windfall from other assets. If that happened would it make a difference on what to do? It seems like in that secnario it might be better to sell the VTSAX with a very small short term capital gain vs VTMGX with the larger long-term capital gain.

Thanks!

Statistics: Posted by moral_hazard — Wed Dec 25, 2024 7:49 am — Replies 4 — Views 231

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