President John Adams' presidency was not doing so well and in order to try to get reelected, he passed the Sedition Act which limited how much the president could be criticized. John Adams was not reelected and in modern times this would be immediately recognized as a violation of the first amendment.
Anthony Comstock was able to convince the governments of New York and Boston to create teams that would go through media and take out anything that went against "Victorian morality." At the time, around the world there were many laws that restricted free speech on the basis of Christianity.
Illinois, Pennsylvania, and South Dakota all ban flag burning. Almost a century later, this would be ruled unconstitutional by the Supreme Court on the basis of freedom of speech.
The Alien Registration Act of 1940 was designed to make speaking against the US Government or democracy practically illegal. This was all part of the Red Scare. Later, Supreme Court decisions would lessen the power of this act
This was the year of the Tinker vs Des Moines case, where two high school students were punished by their school for wearing armbands that protested the Vietnam War. This case got all the way to the Supreme Court and they ruled that students have the right to protest in school because of free speech.
Many NFL players started kneeling during the National Anthem in order to protest police brutality and overall racism in the US. Many players have been punished for this. This is clearly a violation of the First Amendment because both the freedom of speech and the freedom of protest are being ignored.
Some cities in Virginia tried to ban many behaviors on Halloween such as wearing a mask. Not only do these laws make it likely that people of color will be discriminated against as it is unlikely that the law will be enforced consistently, but it directly violates freedom of expression.
During the longest government shutdown in American history, many employees of the federal government haven't been paid and are suffering greatly because of it. Because federal workers have to give up some of their freedom of speech, things can get complicated. Luckily, they are fully within their rights to protest the government shutdown as long as it is during their personal time.
Overall, Americans have not enjoyed the right of freedom of speech to its fullest capacity. While there have been many times where the freedom of speech has been amazing for Americans, if you look through history you can see the very many times that the freedom of speech has been unfairly limited or completely ignored.