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Illustration: Lazaro Gamio/Axios

President Trump’s run of big, unorthodox bets — ranging from negotiating with a nuclear madman in North Korea to depending on friends who turned out to be "flippers" — is looking riskier and less winnable by the day.

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.
  • He rolled big that steel and aluminum tariffs would assert American strength and protect domestic industries. Instead, he managed to alienate allies around the globe and hurt American interests — from automakers to pipeline users to farmers suffering from retaliatory tariffs.
  • He bet on loyalty, believing friends like Michael Cohen, David Pecker and Omarosa would never turn. They all did.

TBD on his public ridicule of Robert Mueller:

  • Trump routinely whacks Mueller and calls his probe a witch hunt. But approval of Mueller's investigation in a Fox News poll last week was 59% (up 11 points from July) — higher than Trump’s, which was 45% in the Fox poll (42% in Gallup).
  • But many Republicans think the investigation is a witch hunt, and Republicans are who he needs to stave off impeachment. It's critical for Trump to make it a red-blue issue, and he's done that.

Be smart … An outside Trump adviser said that when you add it all up, he’s "losing the midterms in spite of a strong economy."

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