When Does Honest Self-Examination Become Destructive Self-Sabotage? "That Guy" and Liberals

Him.  That Guy.  Surely, everyone reading this column has met him.  (Yes, almost without exception, he is a he.)  He holds himself out as a liberal, at least to the left of center, maybe even with some truly progressive commitments.  But still ... still .... still he chooses to spend large chunks of his time telling people with whom he supposedly agrees that they are terrible, that the other side "really has a point," that we are being blindly partisan with our minds wide shut and must mend our ways.  He says he disagrees with conservatives, but still he says that we should be modest and admit to being wrong.  And he says this again and again, on issue after issue, until the only remaining question is: "Wait, tell us again why you think you're on our side?"

That Guy is exhausting.  That Guy is sometimes a self-satisfied scold, but even when he is not being smug, he is a hall monitor who corrects people's behavior.  Not being satisfied with calling us out on our manners, That Guy says that we have been wrong all along on substance as well, on issue after issue.  He is sometimes dubbed "Republicans' favorite Democrat," because he "balances" a discussion by agreeing with the Republicans that Democrats are wrong again and again and again.

I am, I concede, describing a composite as opposed to one or more specific people.  There are degrees of being That Guy, some more extreme than others, but the point is the pattern of behavior.  Quite simply, there are far too many people on the left side of American politics who are driven by that basic, contrarian, let's-undercut-ourselves instinct.  That Guyness is a nervous tic, not a full-blown personality disorder.  But even nervous tics can become extreme enough to make life difficult.  It is ultimately a very immature move, bringing attention to oneself by claiming that everyone else is being immature.

Before moving on, I should emphasize that the underlying instinct under scrutiny here is, in fact, ultimately very much a sign of decency.  We have seen what happens to a political party that drums out anyone and everyone who dares to say anything that Donald Trump dislikes.  Internal discussion and debate is healthy and necessary.  Again, however, there are a bunch of Those Guys out there who lose the plot and end up making everyone else wonder why they even claim to be on our side.

Why bring this up now?  In my Dorf on Law column earlier this week, I talked about how the Clintonian approach to being Democrats was to bash other Democrats, a process called triangulation that Bill Clinton wholeheartedly embraced.  ("New Democrats," the Clinton/Gore team bragged, were willing to preside over the execution of a prisoner with severe brain damage.)  This was relevant in August 2024 because one of Clinton's most notoriously dishonest, bare-knuckled advisors was a guy named Mark Penn, and Penn had written an op-ed arguing that Pennsylvania Governor Josh Shapiro was the best choice to be Kamala Harris's running mate.

There was a decent case to be made for Shapiro, but Penn did not make that case.  Instead, he said that  doing so "would send a signal that Ms. Harris is not captive to the left and that she puts experience ahead of ideology," that Shapiro "could appeal to many moderate Democrats, independents and some Nikki Haley voters on a multitude of key issues," and that he "would provide balance to the ticket and underscore that there is a place for moderates in today’s Democratic Party."  Harris, we now know, chose Tim Walz, and although the Trumpists are trying to paint him as a radical lefty, they would have done that to Shapiro as well.  And it is very clear that Walz appeals to many non-progressives.

But Penn is not That Guy.  Penn is in fact a conservative (note his demonization of "the left," which apparently takes captives) who hitched his wagon to the then-unknown Clinton and found it easy to convince him to adopt conservative policy positions.  Penn tosses around terms like "moderate" to describe a man (Shapiro) who supports school vouchers, which is not a moderate position.  Moderation should not mean "giving conservatives exactly what they want on some things and then compromising liberal positions on others."  Penn (who, as I noted in Wednesday's column, said that Trump's first impeachment was a nasty plot by the liberal "deep state") hates liberals and progressives, but not because he is one of them.

Again, That Guy is different.  He thinks that he is a liberal and that he likes others on the center-left, but he seems to think that his highest calling in life is to concern-troll his compatriots.  On issues large and small, he says, "Well, actually ...," often in a way that barely rises above nitpicking.  I have, for example, found myself in the odd position in recent years of being told that it was unfair to make fun of Trump's Space Force.  When I responded that there was no reason to create a new branch of the military, the retort was, "Well, there's no reason not to do so."  When someone framed a response to a libertarian argument by saying that "this comes out of a badly written novel," another Guy said, "It's not necessarily bad to cite a novel."  Gotcha!

Most recently, when people have pointed out that JD Vance once likened Trump to Hitler, Those Guys everywhere jumped in with, "Well, actually, Vance didn't say that."  What did Vance say? "I go back and forth between thinking Trump is a cynical asshole like Nixon who wouldn't be that bad (and might even prove useful) or that he's America's Hitler."  That Guy says that Vance did not quite say that Trump is Hitler, but Vance did not even say "might be" or anything like that.  At best, Vance said that sometimes he thought that Trump is Hitler, and sometimes he thought something else.  This fact-check, tone-check move has metastasized into unfounded absolution on the flimsiest of grounds.

Again, these are nits, but this is a response to That Guy's nitpicking.  What the heck is the point of that kind of supposed purity?  And this attitude carries through to matters of genuine substance.  How many supposed liberals have responded to Supreme Court reform plans with a quick, "We can't become the party of court-packing"?  Why not say instead that the Republicans have packed the Court, which is true, rather than acting as if people on the left are shockingly violating the sacred independence of the courts?  Similarly, when the US Supreme Court took up the issue of whether Colorado could keep Trump off the primary ballot under the Insurrection Clause of the Fourteenth Amendment, nominal liberals were all over the place offering pearl-clutching arguments about the sanctity of the vote, with one saying that Bush v. Gore "stained" the Court in 2000 and thus that the current Court had to be modest and rule for Trump.

Clearly, that kind of move makes these people feel good about themselves, because it is their own form of virtue signaling.  I'm not one of those pure partisans!!  Good for you.  But even if these contrarian arguments were being offered in good faith -- which is easy to doubt, given that the arguments are typically so tendentious -- the hippie-punching aspect of it is undeniable.  We supposed wackos are arguing for, say, a tax on unrealized income, and the response from That Guy is: "Well, there's probably going to be a constitutional challenge to that, which will make us look nutty, so I'm going to tell liberals to shut up."

I examined perhaps the worst version of this bad habit in my column earlier this week.  There, I noted that New York Times columnist Ezra Klein (who is undeniably on the center-left) decided to say recently that "the negative side of, I think, the liberal personality ... can be a kind of contempt, a kind of smugness."  Do we all know a liberal who has been smug?  Sure.  Speaking as a vegan, however, I can say that the smugness from liberals is often aimed at people like me.  (More hippie punching.)  But contempt and smugness are not a "side" of what Klein asserts is an identifiable "liberal personality."  Republicans generally trade in contempt and smugness, but there is no chorus condemning them.  Klein seems to be saying little more than this: "Sometimes, guys, you really embarrass me."  And then he smears everyone with a broad brush, apparently thinking that doing so is acceptable because he is, what, trying to help?

But am I not doing the same thing?  After all, I am criticizing other liberals for saying things that I disagree with, and for saying them in a way that I find destructive.  How is that different from what I accuse Klein and others of doing?  The difference is that my response does not undermine my policy commitments or give ammunition to the other side.  I am criticizing situations in which That Guy is ignoring facts (distorting Hillary Clinton's words, in Klein's case) or is proving that he is "fair" by focusing on the trees -- or maybe on one leaf on one branch of one tree -- instead of the forest.

That Guy's kind of criticism undermines what self-identified liberal/left/progressive/whatever people claim to want.  That Guy says that liberals are wrong on issues large and small, and he then adds that they are jerks to boot.  What follows are ridiculous self-flagellating rituals in which, for example, a bunch of people trek to diners in the Midwest and talk to guys in John Deere hats, even though the evidence shows that Trump's support was and still is very much a matter of better-off people supporting their narrow self-interests.

There is a reason that Republicans still think that they can make headway against Harrris and Walz by pinning the label "liberal" on them.  George H.W. Bush said in 1988 that Michael Dukakis was afraid of "the L-word" (long before that became a different reference entirely).  Dukakis, Clinton, and a generation of Democratic "centrists" ducked and covered.  As I put it at the end of Wednesday's column, the vibe from these people is: "Well, I know we sorta suck, but ..."

When we make mistakes, we should discuss them and straighten things out.  But doing so by reinforcing negative, anti-liberal stereotypes and saying "I'm not one of them!" is worse than useless.  It is time for That Guy to grow up.