Your greatest volatility always exists in the future so any purely historical analysis is clipping off the tails.
To quote @paulg, history is merely all the data we have so far
i.e. middling backtest but live results are more likely to resemble simulated results.
I would argue that 538 (and many other people making predictive models based on past data) bias too much towards high variance.
E.g. In investing, if you are trying to decide how much leverage to add to an investment portfolio, figure out the largest historical drawdown and double it (at least)