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Prem Watsa Finally Walked Away from His Worst Investment Some investments you hold because they're working. Others you hold because admitting defeat is harder than waiting one more year. Prem Watsa held BlackBerry for 16 of the latter. Fairfax Financial, the Toronto-based insurer Watsa has run since 1985, revealed in a U.S. regulatory filing that it no longer owns any BlackBerry shares, according to reporting from the Globe and Mail. Fairfax once held 46.7 million shares, roughly 8% of the company, bought at an average price of $17.16 apiece. It had been selling down the position gradually since sometime after March 2025, and by early May was down to 26.26 million shares before exiting completely. The math is ugly. Based on when Fairfax sold, the best-case estimate puts the loss north of $288 million on top of an earlier $124.5 million lost selling shares back in 2014. Watsa did earn about $200 million in interest income over a decade holding BlackBerry's convertible debentures, but that doesn't come close to covering the equity losses. In his own 2024 shareholder letter, Watsa called the whole affair "another horrendous investment by your chairman," and pointed out that the same money parked in Meta, Amazon, Apple, Netflix, or Alphabet instead would have grown at least eightfold, and as much as 27-fold, over the same stretch. What makes this notable isn't the loss itself. Every investor, even a great one, eventually buys a BlackBerry. It's that Watsa said so publicly, in his own words, years before he actually sold. That kind of self-critique from a manager overseeing over $100 billion in assets is rare. What it means for youSunk cost is the most expensive trap in investing, and it gets more expensive the longer you wait to spring it. Watsa's BlackBerry saga is a reminder that admitting a thesis has broken, in writing, to your own shareholders, is a discipline worth building even when it's uncomfortable. The size of the loss matters less than how honestly you account for it. |
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