As far as I can tell, there are three aspects of cancel culture of concern to the old left:

1.  They recall when cancel culture was used against the left.
2. They worry that it diverts attention from achieving socialist aims, and indeed makes it more difficult to do so.
3. They believe the younger generation is too soft.

The first point is obvious. Free speech has traditionally been a liberal idea. Those of my generation will recall the Berkeley free speech movement, and those a bit older will recall the Joe McCarthy era.

The second point is less obvious. Here’s Freddie deBoer expressing frustration with defenders of cancel culture:

[C]anceling is so powerless that Bacharach feels no compulsion to discuss it in terms of power. He literally does not discuss the efficacy of canceling. I scrolled down past the bottom thinking I had missed something. He is interested in undermining canceling’s critics, but he spends no time considering the actual material value of the tactic. I’ve said this before, but it bears repeating: canceling is a political tactic that is most often defended with reference to its powerlessness, and this is bizarre. Bacharach defines the negative consequences of canceling as “getting nitpicked by an editor, yelled at on social media, or losing an occasional opportunity to rile up an auditorium.” Jacob: if that’s the extent of canceling’s power, why are you bothering to defend it in one of the biggest magazines in the country? “I’m defending this method to hurt political enemies by pointing out that it doesn’t actually hurt” is not compelling. On the contrary, it demonstrates just how unhealthy and bizarre our political culture has become. . . .

There is indeed a conversation to be had about canceling on the individual level and whether people deserve basic fairness when accused, what kind of fairness if so, and debates to be had about who deserved it and who didn’t. But those have nothing at all to do with politics. Politics is about power. Cancel mobs don’t have it, and they never will.

You wanted reparations; you got Dr. Seuss. Maybe time to take a hard look at why.

Many people who are on the right on economic issues (including me) are frustrated that corporations have enthusiastically embraced cancel culture.  But why shouldn’t they?  Cancel culture is a distraction for the left.  It has almost no impact on profits, whereas socialism would have a big impact.  Actual socialists like deBoer understand this, and not surprisingly are frustrated.

There’s also a reverse class warfare aspect to cancel culture.  In a Bari Weiss piece discussing the woke transformation of elite private schools, she mentions how woke culture is a tool for cool rich kids to bully less sophisticated kids:

Woe betide the working-class kid who arrives in college and uses Latino instead of “Latinx,” or who stumbles conjugating verbs because a classmate prefers to use the pronouns they/them. Fluency in woke is an effective class marker and key for these princelings to retain status in university and beyond. The parents know this, and so woke is now the lingua franca of the nation’s best prep schools. As one mother in Los Angeles puts it: “This is what all the colleges are doing, so we have to do it. The thinking is: if Harvard does it, it must be good.”

I cannot prove that old leftists believe the younger generation is too soft, but reading between the lines I suspect this is the case.  In my view, modern cancel culture excesses often rely on a misapplication of utilitarian theory.

Older cancel cultures focused on “dangerous” ideas, such as atheism or communism.  As the modern world has shifted in a more utilitarian direction, there is less interest in burning people at the stake for being atheists.  Instead, the focus has shifted from dangerous speech to “offensive speech”. Utilitarians worry that if we allow lots of offensive speech, it will reduce the utility of victimized groups.  While this claim seems plausible at first glance, I believe it’s too simple.

Let me use an analogy from camping.  If you are used to a soft life, then camping can initially feel rather unpleasant.  A stick might scratch your arm while you are walking through the woods.  After a few days you get toughened up, and slight injuries that used to bother you in the city are hardly even noticeable.

Before you jump all over this analogy, let me make two points.  First, one can also get serious injuries in the wild, such as a broken leg.  Indeed some campers die while out hiking.  I do realize that members of marginalized groups can be severely harmed by certain types of speech.  Second, just because being scratched by a branch tends to toughen one up, there’s no point in doing so intentionally.  Life will already throw plenty of discomfort your way, no need to go looking for it.

So the cancel culture is not completely wrong; there really are some types of behavior that deserve to be cancelled.  Rather the actual problem is that cancel culture advocates often overlook the fact that vigorous debate makes people tougher, and that if you try to protect people from ever being offended, they’ll become softer and then will end up being offended by things that a person in a previous generation would have simply brushed off.  Cancel culture advocates believe they are reducing the aggregate discomfort suffered by marginalized groups, and yet we may be approaching the point where the movement becomes counterproductive, at least the margin.  And that can be true even if most recent cultural changes discouraging hate speech have been a net gain to society.

I don’t doubt that behavior toward marginalized groups is better today than a few decades ago, but I feel we reached a sort of hedonic treadmill, where increasing wokeness reduces offensive speech at roughly the same rate that it reduces our psychological defenses against insult.  We are like a camper being too careful when walking through the woods.  For instance, does anyone seriously believe that constantly changing terms (say cripple to handicapped to disabled) affects the psychology of the disabled person who hears those terms?  Does a heavy person called obese in 2021 feel less bad than one called fat in 1971?  In the 1970s, we learned that inflation only fools workers in the short run.  The continual invention of euphemisms is sort of the verbal inflation of politeness.  It is equivalent to manipulating the Phillips Curve, and is about as likely to be effective.  In contrast, “fat-shaming” is always bad, whether you use the term ‘fat’ or the term ‘obese’.

The old left grew up in a different era and hence probably see the younger generation as being too soft—just as my parents’ generation felt that us boomers were too soft.  But they also worry that cancel culture will push blue-collar whites, as well as many Asians and Hispanics, into the Republican Party.  This is sort of the flip side of the worry within the GOP that Trumpism will push well-educated suburbanites over to the Democrats.  If both changes occur, then no single party has much of a constituency for socialism.  The old left probably senses that fact.  (BTW, the right has its own cancel culture.)

My own views are hard to explain.  I don’t have any magic formula for determining exactly what should be cancelled and what should not.  But I do believe that a few sensible reforms would improve the situation.  Thus universities could have a board with 10 members, of which at least 3 were liberal and at least 3 were conservative.  Then, before sanctioning anyone for offensive speech, demand a vote of at least 9-1 in favor of sanctions.  That would insure that the speech really was offensive, and that the person wasn’t just being sanctioned for political reasons.  It’s an example of my preference for “rules utilitarianism.”

PS.  If there are any universities that do not have at least three liberals and three conservatives, then cancel the entire university.  Shut it down.