“The hardest thing in the world to understand is the Income Tax.” -Albert Einstein

By Andrea Young on February 23, 2023

By Glenn Frank, MBA, MST- Director of Education

“The hardest thing in the world to understand is the Income Tax.”
-Albert Einstein

Accordingly, do your best to understand tax laws and have them work FOR you whenever possible. We believe you can minimize portfolio taxes without compromising the essence of your investment strategy. Unlike most forms of income, the timing of taxation on capital transactions is largely up to the investor. Regardless of economic gain, taxes are not incurred until investments are sold, and then, with proper planning, tax rates could be far less than the marginal rate on your earned income.  

Schedule D Netting Process
The top half of Schedule D nets short-term, (investments held <1 year), realized gains against short-term realized losses/ short-term loss carryovers from the prior year. The lower half of Schedule D nets long-term realized gains plus capital gain distributions from investments against long-term realized losses/long-term capital loss carryovers from the prior year.

There are three possible outcomes from Schedule D:

  • Net short-term gain and net long-term gain: short is taxed at your highest marginal tax rate and long is taxed at your capital gains rate, (0%,15%, 20% or 23.8%).
  • Net short-term loss and net long-term loss: deduct up to $3,000 against other income and carry forward excess to the following year.
  • Net short-term is different from net long-term: they net against each other to produce an overall net gain or net loss. A net gain is taxed per outcome (1) above, a net loss it is taxed per outcome (2). For example, a net short-term loss of $7,000 and net long-term gain of $16,000 will equal a net long-term gain of $9,000 which is subject to your long-term capital gains rate.


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This is not an offer to buy or sell securities. No investment process is free of risk, and there is no guarantee that the investment process or the investment opportunities referenced herein will be profitable. Past performance is neither indicative nor a guarantee of future results. The investment opportunities referenced herein may not be suitable for all investors.

All data or other information referenced herein is from sources believed to be reliable. Any opinions, news, research, analyses, prices, or other data or information contained in this presentation is provided as general market commentary and does not constitute investment advice. Lexington Wealth Management, HighTower Advisors, LLC nor any of its affiliates make any representations or warranties express or implied as to the accuracy or completeness of the information or for statements or errors or omissions, or results obtained from the use of this information. Lexington Wealth Management and HighTower Advisors, LLC assume no liability for any action made or taken in reliance on or relating in any way to this information. The information is provided as of the date referenced in the document. Such data and other information are subject to change without notice. This document was created for informational purposes only; the opinions expressed herein are solely those of the author(s) and do not represent those of HighTower Advisors, LLC, or any of its affiliates.

Lexington Wealth Management, HighTower Advisors, LLC nor any of its affiliates provide tax or legal advice. This material was not intended or written to be used or presented to any entity as tax or legal advice. Clients are urged to consult their tax and/or legal advisor for related questions.

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