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This question will use Freedom House's Freedom in the World report, resolving YES if the United States fails to be classified as "free" in any annual report about a year in the 2020s.
Note that Freedom in the World reports cover the previous year, being published in February or March. This is relevant because the last report about a year before 2030 will come out in 2030 and be titled "Freedom in the World 2030."
The classification of a country as "free" (as opposed to "partly free" or "not free") depends on two separate measures, Political Rights and Civil Liberties, which produce a country's status by comparison to the following table (see methodology for more detail):
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In the 2023 report, the United States scored 33 out of 40 points for Political Rights, and 50 out of 60 for Civil Liberties for a total score of 83, a decline since the 2017 report when the United States scored 89.