Considerations for a Long-Short Strategy to Manage Capital Gains

The long-short strategy is an advanced investing option that investors with concentrated positions and large capital gains may want to consider.

CFA®, MBA
Sr. Director of Investment Strategy
Published May 23, 2025

Key Takeaways

  • Market volatility can create opportunities to enhance after-tax returns through strategies like tax-loss harvesting.
  • Long-short strategies aim to track a market benchmark while generating tax losses and potential alpha through systematic security selection.
  • These strategies can be especially effective for diversifying concentrated stock positions or offsetting gains from business or real estate sales.
  • While long-short strategies can offer meaningful tax and portfolio benefits, they are complex and not appropriate for every investor.
  • Because capital gains are deferred — not eliminated — long-short strategies require a long-term commitment and a thoughtful exit plan.

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