45. Scott Thompson’s Costly Decision at Yahoo
Year: 2012
Location: California
Company: Yahoo
Estimated Damage Value: $54 million*
Scott Thompson’s tenure as Yahoo’s CEO in 2012 quickly became notorious. Initially brought on board to lead, he instead incurred substantial losses by mishandling a crucial stake in Alibaba, marking a costly era for Yahoo.

Under Thompson’s leadership, Yahoo made the ill-fated decision to sell 20% of its Alibaba stake, valued at $30 billion then. Following the sale, Alibaba’s worth surged to over $300 billion, resulting in a staggering $54 billion loss for Yahoo.