What was behind Jamie Dimon’s bet against a second term for Trump?

JPMorgan Chase CEO Jamie Dimon made headlines last month for betting President Trump will last only one term in office.

The remark came during an event hosted by the Economic Club of Chicago, where Dimon, current chairman of the Business Roundtable, took “several digs” at Trump, per Bloomberg Politics, including a swipe at the president’s stance toward Mexico.

In the context of his larger relationship with this administration, however, Dimon’s diss is more interesting than a simple prediction.

After congressional Republicans released tax reform legislation in early November, the CEO published a statement referring to it as “significant progress toward” the goal of creating a modernized tax code, complimenting GOP leaders both on Capitol Hill and in the White House. “Congress and the Administration clearly appreciate the importance of getting pro-growth tax reform finished, how it will improve the economic security of all Americans and how it will give American companies the ability to compete equally in the global economy,” Dimon said. “We support this tax reform effort because it is good for all Americans.”

From his perch atop the country’s largest bank, Dimon’s political musings often focus on considering what’s best for average Americans, though he’s no fan of progressive populist solutions, as evidenced by his past barb-trading with Sen. Elizabeth Warren, D-Mass (the two recently met). While he reportedly turned down an offer from the Trump transition team to serve as Treasury Secretary, in May, Dimon broadly endorsed Trump’s economic agenda, arguing the president’s “economic agenda, about corporate tax reform, infrastructure, regulatory reform, is the right agenda for growth.”

Relatively mild as it’s been, his support for Trump has inspired some pushback, captured by this Vanity Fair story in May probing the motivation behind such quotes as, “I would try to help any president of the United States because I’m a patriot.” Dimon has thus rankled shareholders by not putting sufficient distance between himself and Trump.

But while the powerful CEO has been fairly outspoken when it comes to the Trump administration, it hasn’t all been positive.

Up until now, he had previously broken with Trump’s decisions on the Paris accords and DACA, and sent his staff an email disavowing the president’s response to violence in Charlottesville.

Dimon’s 45-page annual letter to shareholders sent last April “reads like a manual for how best to grow the economy, instructing politicians on how they should go about dismantling financial regulations such as Dodd-Frank, enacting tax reform, creating jobs and solving income inequality,” as described by Fortune. The letter never mentioned Trump by name, and aligned generally with him on topics like tax reform, but also seemed to diverge on trade, immigration, and other matters.

Taken as a whole, the letter outlines a compelling platform built on policy prescriptions borrowed from both parties.

Dimon’s frustration with perceived stagnancy in government also bubbled over publicly in a July conference call. “We have become one of the most bureaucratic, confusing, litigious societies on the planet,” said Dimon. “It’s almost an embarrassment being an American citizen traveling around the world and listening to the stupid shit we have to deal with in this country.”

Now it may be time to wonder whether Dimon is deliberately dipping his toes into the waters of more muscular Trump criticism.

Dimon affiliates as a Democrat, but only “barely,” by his own description. His long FEC record of campaign contributions is mixed, but mostly benefits Democrats.

Even so, at that the same Economic Club of Chicago event where he predicted Trump would lose, Dimon made clear he believes his own party needs to be “pro-free enterprise.”

Looking ahead to 2020, Dimon emphasized to the audience that Democrats will need “to come up with a reasonable candidate” in order to defeat Trump.

But who could Dimon have in mind?

Probably not Sen. Warren. In the past, he’s suggested Detroit Mayor Mike Duggan for the job. But there is some speculation that Dimon could be interested in making a run himself. The Financial Times reported in August that “[f]ormer colleagues believe he might throw his hat into the ring.”

“One former JPMorgan senior manager recently let slip to City Insider that he was convinced Mr. Dimon would run for president in 2020,” the story claimed. Others have urged him to make a go of it as well.

Dimon said he “would love to be president,” but dismissed the possibility in 2016.

If his party’s field shapes up to include serious candidates whose records are hostile to the business community, perhaps Dimon might find a place for himself at the table in 2020. Maybe not. But it sure seems as though his ambitions are at least worth paying attention to.

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