Trump the Gambler – The American Conservative

We will hear a lot more about President Donald Trump the dealmaker in the coming days as the tariff wars continue and some kind of talks with Iran begin. That’s pretty central to Trump’s self-image, and it is a big part of what will determine his success or failure in his second term.

But Trump the risk-taker is the bigger story right now. It is somewhat ironic that before the tariffs and the stock market dominated the headlines, the main Trump-related controversy was whether he intended to seek an unconstitutional third term. Whatever he says when reporters ask him about 2028, nearly all his behavior points in the opposite direction.

Trump is spending, not hoarding, political capital. He is taking risks with the stock market that he would have never taken in his first term, when he actually was planning on a second term, absent the pandemic. Very little of what Trump is doing on tariffs, immigration, spending via DOGE, and executive orders on a host of issues suggests that he is expecting to be able to accomplish much past the midterm elections, much less anything later than that.

To that end, Trump isn’t counting on Republicans maintaining control of the House more than 18 months from now or perhaps even staying unified for many weeks longer. Trump is biting off an awful lot and nearly all of official Washington believes it is more than he can chew.

When Steve Sailer wrote 20 years ago about the new “risk-taking conservatism,” he was referring to the policies of George W. Bush’s administration: invading foreign countries and alienating their populations while at the same time inviting them to immigrate to the United States in large numbers; partially privatizing Social Security by investing a portion of payroll tax receipts in the stock market on what turned out to be the eve of a major financial meltdown; a doubling down on globalism in the aftermath of the 9/11 terrorist attacks.

Trump’s entry into national politics and leadership of the Republican Party marked a reversal of nearly every one of these policies. Yet he has hardly been risk-averse in either his first term or, especially, his second. The entire lesson of his political career has been that fortune favors the bold. He has regularly made Houdini-like death-defying escapes from seemingly insurmountable crises, some of them traps laid by his enemies, many others partially or entirely of his own creation.

“It’s the only chance our country will have to reset the table. I could have come in and had an easy term,” Trump said at the White House earlier this week. “But no other president would be willing to do what I am doing or even go through it.”

Trump wants to make deals with Iran, with Russia and Ukraine, on Israel and Gaza, with dozens of countries seeking relief from his tariffs. But he is also taking significant risks on almost every one of these fronts.

One of the reasons Trump had more success with international dealmaking than with domestic legislative deals during his first term is that he understands them as transactions but often has a blind spot for matters of principle. His stronger political position has paradoxically helped him do better with congressional Republicans this time around, though reconciliation will be a big test, but this tendency has cropped up at times in his diplomacy, too.

For example, Trump genuinely believes if given a better option few Palestinians would willingly wish to remain in war-torn Gaza. But that misreads at least one of the dynamics that has made Middle East peace so elusive for decades. Where Trump in his first term encouraged a sort of pan-nationalism, especially in the West, he’s often had the opposite effect this time around, almost singlehandedly sparking a Liberal revival in Canada.

Closer to home, Trump gets annoyed with his party’s surviving establishment RINOs and romantic ideologues alike because he sees both as obstacles to getting things done. But some of them have genuine principled disagreements, and many in the second camp would like to be his most reliable supporters. 

Trump is now testing the political will of all his allies, foreign and domestic. The end result could be delivering on his America First campaign promises as never before and likely transforming the Republican Party for years to come. Or we could be looking at something closer to the total opposite of that outcome.

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