When do you think our country had the most freedom?

Roy Childs, Jr. said it best when he wrote:

"Libertarians themselves should take heart. Our hope lies, as strange as it seems, not with any remnants from an illusory "golden age" of individualism, which never existed, but with tomorrow. Our day has not come and gone. It has never existed at all. It is our task to see that it will exist in the future. The choice and the battle are ours."
 
Sure, there is no doubt that America was a better country than anywhere else during the years you mentioned. But this thread is about comparing America to itself across different time periods. And I cannot see why the America of 1995 was less free than the America of 1795 or 1855, besides a few economic factors like tax rates or government spending or sound money.

Freedom is a subjective measurement of which choices an individual is allowed to take.

There has been a great amount of freedom in America for rich, white males of the appropriate religion. This freedom has declined as time progressed through taxation, contractual limitations, prohibitions.

Historically there was little freedom for the poor, women, racial minorities, religious minorities, etc. But they have seen an expansion in their freedoms, having more access to wealth, more rights to make contracts, more political sway.

I only know that I have fewer freedoms than I did when I first became an adult. How that compares to other people living in the geography of North America throughout history, I can't know.
 
In spite of considerable federal efforts to homogenize the country, vast regional differences in freedom still exist across these united states. For instance, there are still counties (like the one where I live) where you can buy a piece of land for little money and construct practically anything you want (ponds, unconventional housing, junk yards, gun ranges, race tracks, sawmills, etc.) without asking for anyone's permission (or forgiveness). And then there is the other 75% of the country where 98% of the population chooses to live with considerably less freedom... presumably for economic, cultural, and aesthetic reasons.
 
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