Yglesias takes on a few counterfactuals in his latest "mailbag." It demonstrates some of his weaknesses as a thinker.
My understanding is the Yglesias was a philosophy major, not a history major, and it shows. His idea that changing a single event could dramatically reshape history seems flawed. He cites For All Mankind as an example. Now, I too enjoy the show. It's fun. But it's shit history. It's a fun parlor game to imagine that a single pivot point could reshape everything, but the name of his damned blog is Slow Boring. That's a reference to Max Weber's quote about politics being the slow boring of hard boards. Change happens slowly for multiple reasons.
For instance, the coming of the Civil War was broadly about the expansion of slavery into western territories, but it also touched on the radicalization of the South and then the North over the Fugitive Slave Act and Dred Scott. It was also caused by specific acts of violence like the Caning of Sumner that heralded a broad breakdown in political life. And it was also the many other things that the Republican Party stood for in 1860: homesteads, a transcontinental railroad with a terminus in the North, higher tariffs and a central bank. So, if you were to say, "What if Lincoln weren't elected in 1860?" you are proposing that only Lincoln's election caused the Civil War. That's nonsense.
This fascination with "one weird trick" comes up when Yglesias talks about policy. He assumes that policy - especially the policies he likes - will unlock some sort of easy majority for center-left politics. People, in fact, vote for a myriad of different reasons. If they are strictly policy voters, they've largely made up their minds years ago. The policies of the two parties are pretty different. He points to Trump not pushing the Paul Ryan fiscal austerity model as somehow unlocking a bunch of voters who were convinced that Trump wouldn't cut Social Security benefits. This accounts for him winning 2,000,000 more votes than Romney.
Or maybe people just liked the celebrity "billionaire." Or didn't like Clinton, which was true, although Clinton won roughly the same number of votes as Obama in 2012.
My point is that world events are multicausal and ignoring that is a massive problem in your cognition of the world.
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