It seems that the scenario Cowen put forth and the St. Petersburg paradox are not quite the same? In St. Petersburg (at least as Wikipedia describes it) you walk away with the accumulated winnings, whereas in the example put forth if you lose you walk away with nothing.

I was wondering because it would seem with Cowen's example the expected value is just $1 (ignoring the 51% edge). The 51% edge ends up making the expected value infinite, so the intuition lines up even though the exact details don't.