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.

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 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.

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.

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).

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."