Isn't one of his great sayings "be greedy when others are fearful" ?
IIRC the market didn't have much lower to go in 2008-2009 so if he bought at (or close enough) to "the bottom" then he wasn't really taking on much risk anyway.
Did it myself last year when COVID started and the market plummeted. Went on a shopping spree with some spare cash I had, lots of decent shares being effectively sold at a discount, all you had to do was "be greedy when others were fearful" ... pick something up at a 20%+ discount and then just sit and wait (and be prepared to wait a few months to a year). And with COVID it was pretty clear that as long as it wasn't an airline or hospitality stock, the odds would be in your favour.
There is some mythology here that is out of tune with the reality of using your power to get favorable deals.
When Warren Buffet bought financial stocks in 2008-2009 the deals were done in such a way he could not lose money easily, or at least had a much lower chance than any ordinary investor.