Billionaire oil investor T. Boone Pickens sold his entire stake in Yahoo at a loss in frustration over the failure of the company to reach a deal with Microsoft.
Pickens had purchased 10 million Yahoo shares in May, backing an attempt by activist investor Carl Icahn to force the Web portal to rekindle negotiations with Microsoft, which had offered to buy Yahoo for $47.5 billion.
Pickens did not disclose how much he lost on the investment. According to FactSet Research, Yahoo shares traded at an average of $26.78 during the month of May, and had currently fallen to about $20. This means Pickens' loss could be more than $50 million.
Yahoo reached a settlement with Icahn and two of his nominees last week. The deal with Icahn spared Yahoo from a proxy battle at its annual meeting on Friday.