To use the same analogy, in evolutionary terms every creature alive has won the Powerball drawing, not only once millions of times. Each little incremental change was beneficial. The odds of one mutation being beneficial are astronomical, yet it supposedly happened millions of times in the same line for billions of creatures.
In billions of years, there have been a large number of experiments. It is improbable that I'll win the Powerball with one ticket, but if I buy 67 million tickets, it's almost certain that I will win.