Is it always better to sell long term cap gains stock before short term stock from the same company?

This is an ongoing debate I'm having with some friends. Conventional wisdom says when choosing from multiple share batches of the same company, if one is taxed at short term cap gains and the other at long term, always sell long term first. However there appear to be some edge cases where this isn't true, esp if you want to maximize your immediate take.

Answer:
I don't see any case that this would make sense. If you are taxed at a higher rate this will cut more deeply into your "immediate take" as you put it. The only other consideration that I can think of is to control how much you make you may wish to sell Lots purchased closer to the current sale price to reduce the capital gains altogether.
As a general rule long term first, but there are many scenarios that could make the reverse true.

If you have some carry forward short term capital loss (or decide to dump a looser for a current loss), then selling short term stock has no tax obligation to the extent of the loss.
as an example, if you are in the 30% bracket and sell stock for a $10,000 short term gain, you only need a $5,000 loss to give you the same tax obligation for a $10,000 long term capital gain.

If you will definitely liquidate the entire holding before the short term portion can turn long term and the stock is rising, it may be better off selling the short term first taking the tax hit and getting the add ional gain on the long term portion.

If you want to maximize your immediate take, and the long term stock was purchased at a much higher price then the short term, then the shear volume of short term stock is higher even after the tax hit.

If you are doing this in a retirement account, it doesn’t matter

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