It’s...important to acknowledge that economic rights are not in some inherent conflict with civil rights. In fact, we have significant historical evidence showing that legally enforced property rights (and other forms of economic liberty) actually undermined the Jim Crow regime. Most famously, the NAACP won its first Supreme Court victory in 1917 by arguing that a residential segregation law was a racist interference with property rights under the 14th Amendment.
Finally, keep in mind that Plessy v. Ferguson, the notorious 1896 Supreme Court decision that enshrined “separate but equal” into law and become a symbol of the Jim Crow era, dealt with a Louisiana law that forbid railroad companies from selling first-class tickets to blacks. That’s not a market failure, it’s a racist government assault on economic liberty.
Very few things are as antithetical to freedom as government-enforced segregation. What's tragic about the arc of American conservatism is that it could have retained a Lincolnian long-term defense of freedom as a way to condemn both Jim Crow and affirmative action ... until Nixon's cunning and Reagan's opportunity muddied the cultural waters. Now, conservatism is almost defined by Southern identity and regrets. As I said: tragic. And, whatever he meant to say, Rand Paul has just made it worse.
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