This will end in tears if it happens, although the pairing of two Jacksonians in Trump and Webb is so obvious that I once floated Webb as a potential VP pick for POTUS before he tapped Mike Pence. They’re both populists, both contemptuous of Washington’s elite consensus, both straddlers of partisan lines, both believers in a strong military, but both also suspicious of military adventurism.

They’re also both irascible and strong-willed, and would be having alpha-male screaming matches within five minutes of Webb joining the team. But since our politics is now a lurid reality show and pulp drama requires freakishly combustible personalities, it seems inevitable that he’ll soon be joining the cast.

I mean the cabinet.

The Trump administration is considering Jim Webb, a former Democratic senator and Reagan-era secretary of the Navy, to be the next defense secretary, according to three officials, potentially bypassing more hawkish Republicans whose names have been floated to replace Jim Mattis…

Representatives for Vice President Mike Pence and Mick Mulvaney, the acting White House chief of staff, have reached out to Mr. Webb, one of the three officials said. Separately, a senior Defense Department official confirmed that Mr. Webb’s name had been circulating at the White House. Those two and the third official all spoke on the condition of anonymity to describe the internal discussions.

Would Webb would be open to a job offer from Trump? I think the answer is — or was? — clearly yes. Benjy Sarlin describes Webb as “MAGA curious” but that’s putting it mildly. Read this account of what he said a week after Election Day 2016. He saw Trump’s ascendance as a potential paradigm-shifter in America, calling it “an opportunity to reject a new form of elitism that has pervaded our societal mechanisms” and “an opportunity to reshape our national [foreign policy] strategy in a way that otherwise has not been possible.” Plus, this:

Webb called Trump an outsider who spoke truth to “hard-working people out in flyover land” who have been abandoned by both parties. But he focused much of his critique on the Democrats, whom he said have drifted from their historical position as the “party of Franklin Roosevelt.”

“That party descended from the party that had championed the rights of working people — regardless of race, creed, gender or any other differentiation — to the point that it made white working people their most convenient whipping posts. Particularly white males,” Webb said. “It’s clearer now than it was 10 years ago when I was trying to put this on the table.”

Until Trump came along, probably no one in American politics had been more outspoken about the hardships faced by the white working class than Webb had. He’s a natural pair with Trump in that sense. He’s a natural pair with him on foreign policy too. From the day before Inauguration Day 2017:

[H]is administration should break the damaging “turnstile” that has given an unelected elite far too much power, particularly in foreign policy. What can one say of an establishment whose members repeatedly swap slots in law firms and think tanks for titles in various presidential administrations but rarely come up with fresh, independent advice? How can one set of “Republican” advisers persuade George W. Bush to make the strategic blunder of invading Iraq, and then a new set of “Democratic” advisers lure Barack Obama into the debacle of the Libyan intervention? It was no accident that many Republican mandarins endorsed Hillary Clinton last year. The new administration should bid them all goodbye. Rex Tillerson’s selection as secretary of state is a welcome signal to that end.

That ended up presaging Trump’s critique of Mattis, the “Mad Dog” turned “moderate dog” who wanted to continue all of the interventions abroad that had been handed to him by the last administration. Trump wants someone who thinks differently on foreign policy than the Washington consensus; Webb wants a president who does the same and got one in Trump. Would Webb accept a once-in-a-lifetime opportunity to help reshape U.S. defense strategy by a commander-in-chief who shares his vision broadly? Quite possibly, yeah. I had him in mind as a potential defense secretary within a week of Election Day two years ago, in fact.

But that was then, this is now. Gut-check time for Jim Webb: Having spent the last two years watching Trump demagogue cabinet members like Jeff Sessions, does he really want to take this ride? On a more basic level, how much does he respect the man whom Tammy Duckworth, another veteran, once called “Cadet Bone Spurs” in honor of his mysterious Vietnam deferments? Webb must realize that no matter how broadly simpatico he and Trump might be on foreign relations, eventually a moment will come when they disagree — or, worse, when the Pentagon doesn’t perform to the level Trump is expecting. And Webb will be scapegoated for it. He’s more likely to be flamed on Twitter if something goes wrong than to get the magnanimous “buck stops here” treatment from the White House. Plus, however much Webb might prefer a more “modest” foreign policy, there are destined to be days when Trump says something weird and off-putting, like engaging in apologetics for some low-rent autocrat abroad. Does Webb want to have to defend that? Does he want to deal with the drama of the daily tweets? What happens if Trump’s foreign-policy views suddenly and inexplicably turn hawkish again, with a new round of bombing Syria ordered because Lindsey Graham made an especially persuasive case on the golf course one afternoon?

And does Trump want to have to manage a guy who, for all his talents, has had an unhappy history in government? Jon Gabriel reminds us that when Webb took over the Navy in the Reagan administration, he ended up quitting 10 months later in protest of his budget being too small. (“I’m not a good bureaucrat in [that] the tedium of the bureaucracy does get to me.”) He was elected to the Senate in 2006 and retired after a single term, apparently frustrated there too. Installing Webb as SecDef might for once cause friction between Trump and a cabinet member that’s driven by the latter, not the former. Their personality clash has the potential to balloon from amusing-reality-show-drama levels to really toxic dysfunction. Which is bad for any government agency but for the Pentagon especially.

Or maybe I’m totally wrong, they’ll hit it off, and Webb will help shepherd a true populist takeover of Trump’s government. Exit question: Trump/Webb 2020?