Tycoon Prem Watsa has added $148.95m of what he has called "ridiculous cheap" shares in his giant Canadian marine insurance and shipping investment company Fairfax Financial Holdings.
The chairman and CEO said he had bought 482,600 subordinate voting shares.
Watsa said: "At our AGM and on our first quarter earnings release call, I said that our shares are ‘ridiculously cheap’.
"That statement reflected my recognition that in the 35 years since Fairfax began, I have never seen Fairfax shares sell at a bigger discount to their intrinsic value than they have recently."
He added: "I have now backed up my strong words by purchasing close to $150m of Fairfax shares in the market over the last few days, as I believe that this will be an excellent long term investment."
The group posted a net loss of $1.26bn in the first quarter as coronavirus took its toll on investments.
The fund is a big player in the Lloyd's of London insurance market. It is also the biggest shareholder in Canadian boxship owner Seaspan and Greek shipping lender Eurobank, and it is a major investor in Indian tanker owner Seven Islands Shipping.
Watsa is an Indo-Canadian billionaire, born in 1950 in Hyderabad, India. He has been called the "Canadian Warren Buffett".
In 2015, Fairfax won support for its $1.88bn bid for insurer Brit from the target company's private equity backers Apollo Global and CVC Capital Partners, only a year after floating on the London Stock Exchange.
Fairfax thus became one of the larger players in the Lloyd's of London market.