Trump's gambling losses

The big picture: Consider his wildest bets — from engaging with North Korea to his ongoing trade war with China — all made largely against the advice of advisers and most GOP leaders.

He continues to play footsie with Kim Jong-un, insisting he can get the lying, nuclear-armed oppressor to surrender his arms. But Trump — after falsely declaring there was no longer a nuclear threat from North Korea after his Singapore summit — was forced to cancel Secretary of State Mike Pompeo’s visit because the North Koreans show few signs of cooperating.

He wagered he could bring peace to Middle East because of his unique deal-making skills and his bond with Israeli Prime Minister Benjamin Netanyahu. Now, after moving the embassy to Jerusalem, the Trump team is preparing to release a peace plan after months of no-contact with the other negotiating partner: the Palestinians.

He keeps escalating his trade war with China — certain Xi Jinping will buckle, even though nobody on his team has true visibility into Xi’s mental state. Trade talks with China are at a standstill. And while Trump’s big bet could pay off with a better ultimate deal with Beijing, there’s a risk the tit-for-tat tariff war could, in the meantime, hinder economic growth and put thousands of Americans out of work.