President Donald Trump has been accused of being the one without the cards at the poker table when it comes to standing up to Iran's leaders, compared to Ukraine's President Vladimir Putin and other leaders. The author argues that by blocking Iran from exporting its oil, he could force Tehran to negotiate on his terms. However, Iran is betting that by preventing the Strait of Hormuz from shipping oil, increasing gasoline and food prices for Americans and allies, Trump will act in accord with his TACO label: Trump Always Chickens Out. The article also suggests that small powers and small groups can leverage information-age tools to gain asymmetric advantages in geopolitics. It suggests that this is a new era in which small powers can use these tools to disrupt mass disruption anywhere on demand. The authors also suggest that the next generation of cyberhackers will be the next challenge to nations such as China and America.