Watsa's determination to be personally involved in a "messy corporate implosion" speaks to his own pride, his affection for Canada and his reluctance to walk away from what could be one of the worst moves he ever made, The New York Times reported.
"Psychologically speaking, he thinks he's the Warren Buffett of the North," the report quoted a person who has followed Watsa's ventures closely as saying.
"He didn't understand the extent the brand recognition mattered here," this person said.
He said Watsa favoured investing in distressed firms with comparatively few shareholders, but BlackBerry was a "notable exception".
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"When it's down and you can't find a single person to help it, that's where he wants to be," the report said.
"Typically, he does these things in not such public high-profile companies. The rules of the game that he applied over his career don't work in a liquid stock like this," the person added.
In late September, Fairfax had made an offer to buy BlackBerry but as the takeover deadline loomed, Watsa's firm failed to find co-investors.
Last week, Fairfax and BlackBerry announced a new deal that would raise USD 1 billion in cash through convertible debt sold to a combination of Canadian, American and Qatari investors.
A professor of finance at York University in Toronto Douglas Cumming said that the spotlight on BlackBerry's problems will further erode confidence in the brand.
"There have been a lot of smarter people looking at this, and they can't seem to make it work," he said.