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Yahoo is in ‘trouble,’ said former CEO who looked at bidding on the company

As Yahoo prepares to report quarterly earnings — and perhaps a buyer of its core business — the former interim CEO said he's expecting a bruising for the internet pioneer.

"I think the prediction is pain," Ross Levinsohn, former interim Yahoo CEO, told CNBC's "Fast Money: Halftime Report" on Monday, quoting iconic fight film "Rocky III." He said he'd have a hard time seeing the core business going above a $5 billion bid.

"There's just an incredible amount of work to do," Levinsohn said.

It comes as Yahoo has faced shareholder pressure to sell its internet assets, as its shares in Alibaba have soared in comparison.

"The core of it is still fantastic — great people, terrific brands," Levinsohn said. "But I think the focus of where they invested ... just has not paid off."