In 1990, he was on the right side of the Tokyo market crash, and 17 years later, his bet against the US housing market bubble left him with billions of dollars in profits while less prescient peers took a battering.
His 2011 investment in Bank of Ireland the only domestic Irish bank not forced into state ownership after a financial crisis has almost trebled in value to 845 million euros ($1.15 billion).
Investments in Greece and a $4.7-billion bid for BlackBerry, which has faded almost to irrelevance in a competitive smartphone market, fit the pattern of contrarian investments, but its too early to say if they will succeed.
Weve got lots of cash, weve got 30% cash, Watsa told Reuters in a rare interview by telephone, referring to the portion of his fund that is invested in cash.
Reticent about what many investors have seen as the bet of the year in US equities, where the broad S&P500 index of leading shares has gained more than 26% so far in 2013, Watsa said the market was overstretched.
Were quite concerned about the US markets in terms of how high they have gone. Its not often that we put our money at risk. Were very cautious, broadly speaking, in the investment business, he said.
At least in the US and Europe, inflation has yet to come up in any significant way... In both areas its close to 50-year lows in spite of all of the central bank action. We worry about those kinds of things.
Watsa spends considerably less time worrying about Ireland, where he said he had invested about $700 million on property investments and his Bank of Ireland stake (at a cost of about 300 million euros, or $407.63 million).
The country was in the first year of its sovereign bailout when Watsa and Bill McMorrow, head of US-headquartered real estate investor Kennedy Wilson, brought together five investors who pumped 1.1 billion euros into the banks 2011 bailout.
The yield on Irelands benchmark 10-year bond topped 13% and Bank of Irelands main rival AIB had to accept a bailout that left it 99.8% state-owned as the country plumbed the depths of its financial crisis.
Less than three years after, Ireland is within days of exiting its sovereign bailout, its 10-year bonds are commanding an interest rate of about 3.5%, unemployment is falling and property prices are starting to creep higher.
Watsa, whos only experience in Ireland prior to the bank deal was serving as best man at a friends wedding in the five-star K Club golf resort an hour from Dublin, travelled to Dublin monthly for Bank of Ireland board meetings while a director. He stepped down in July, passing the baton to a Fairfax colleague Bradley Martin, with fond memories.
We like Ireland and we also like Greece, he said, adding that Prime Minister Antonis Samaras was doing a very good job.
Fairfax was linked with an investment in National Bank of Greece in March, when the bank said the Canadian investor had expressed interest in the recapitalisation.
Fairfax did not ultimately participate, but in October Watsas company announced it would increase its stake in property company Eurobank Properties from 19% to 41% in a share issue expected to be carried out in April 2014.
Fairfax has been tipped as a possible investor in its parent company Eurobank, where the Greek authorities are trying to find anchor investors to take part in a 2-billion-euro capital raise.
Weve made many investments in common stock in Greece, and Eurobank Properties...and of course well look at other opportunities in Greece, said Watsa, declining to comment on Eurobank specifically.
The bid for BlackBerry was by far his most audacious play of 2013. He failed to raise enough finance for the $4.7-billion bid to take the firm private, and instead led a consortium that funded a $1-billion loan to fund a turnaround.
Management has been overhauled, including the November 25 appointment of interim chief executive John Chen, who Watsa said would be there for the long haul.
You never look back, you deal with the hand that you have, theres no use looking at whether you can get four aces or a flush, you deal with the hand that you have, he said.
We think BlackBerry is an iconic company, an iconic brand, its known worldwide... Its a company that deserves to exist and with John Chen it will.
But he may have to persuade some of his Irish friends. Richie Boucher, chief executive of the Bank of Ireland, who Watsa effusively praises, for one is a devoted iPhone user. I guess the Bank of Ireland are not perfect, Watsa laughed.