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Yahoo's prominence in the headlines, from its email hack to the report of the government monitoring its users' emails, is "troubling" to Ross Levinsohn.
The former CEO of Yahoo said it was likely that the company knew about the scandals that have now been brought to the public eye and disclosed neither to Verizon, he told CNBC's "Fast Money Halftime Report."
Levinsohn recalled a group of employees who worked at Yahoo during his time there colloquially named "The Paranoids," who monitored the company's online system day in and day out, searching for unauthorized breaches.
"They were perhaps the smartest people in the entire company and were on top of things, so the idea that this happened and they didn't know about it, it just doesn't make any sense to me," he said.
And, if he were Verizon, which acquired Yahoo for $4.8 billion in July, Levinsohn would be hedging his bets.
"If I were them, just from a business standpoint, I'd probably reserve a bunch of money against the deal or go back to Yahoo and ask for a discount," he said, though he admitted that that could reopen the acquisition process in case a different company would be willing to pay more.
Levinsohn called the situation "the Kardashian effect for internet companies" because of the compounding craziness that has surrounded his former employer.