UPS has long been considered one of the safest names in the transportation and logistics industry. Known for its iconic brown trucks, its global air fleet, and its ability to handle both less-than-truckload (LTL) and truckload (TL) freight, the company has rewarded investors with dividends and reliable growth for decades. But lately, things have changed. The company’s stock has collapsed from its pandemic highs, falling as much as 58% in some of the positions I manage. Across three separate accounts, I recently made the difficult decision to sell, locking in significant tax losses. Those losses hurt, but they also provide an opportunity: by harvesting them now, I can re-enter UPS stock after my wash sale period expires on September 27, 2025, and likely at a lower price. In this article, I’ll outline where UPS went wrong, why I believe current leadership is failing, the risks of its restructuring strategy, and why I still see value in the company long term—just not until some course ...
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