I met some Singaporeans at a conference this year and it was interesting hearing how much they appreciated the fairly militant laws and enforcement. They understood the tradeoff they were making and welcomed it. It made me realize that even though their freedoms were nominally limited, for them personally they were actually enhanced.
You’re maximally free in an environment that best facilitates your normal, or preferred, mode of being. For example: Tom Brady is optimized in a highly restrictive environment. He requires a domain with rigid rules and enforcement to function at peak capacity for his talents and how he likes to exist. And he actually welcomes this constraining situation, he seeks it out. It's where he's most capable.
Is there a freedom tradeoff here for him really? These "restrictions" aren't really restrictions to someone who wants the confines of the system. This concept is abstractable on a societal level. If you have no desire to operate outside the circle drawn for you, you're still free in the circle.
If you're completely content living inside a circle with unyielding boundaries, you're actually more free than if you lived in a space with no boundaries. Because definitionally the boundaries almost exclusively only limit others' abilities to act upon you.
Some people are liberated when they can walk anywhere they want at night. The rigid rules that made that possible don't actually limit their preferred existence. Their normal mode of being is best accomplished here; the cage protects them, it doesn’t limit them.
I have too disagreeable a personality to exist happily with constraints like this, but I understand how others could.
If it isn’t obvious, these thoughts are defending the Singaporean model. In some ways people there are much more free there than in the US; try walking around parts of NYC and SF at night.