Why did the Stamp Act limit the freedom of the press?

Answer 1

The Stamp Act was passed in 1765 by the British Parliament to raise money to pay its debts after the Seven Years War (aka the French and Indian War), which ended in 1763. It required all paperwork, including books, newspapers, legal documents and playing cards, to bear a special stamp in order to be considered legal. Colonists were required to buy these stamps from government agents.

It doesn't seem like it was a major issue as pertains to freedom of the press, but the perception was that the government agents who sold the stamps could theoretically withhold selling the stamp to a publication they didn't like, rendering it illegal. The penalties for publishing materials without the stamp were steep, and were enforced by special military courts rather than the normal colonial jury courts.

The main issue behind the Colonists' dislike of the tax is "taxation without representation" rather than possible censorship. Parliament was raising taxes on Colonists, but the Colonists were not allowed to vote in Parliamentary elections. So the Colonists claimed it was unfair for Parliament to raise taxes on them, and a violation of their rights as Englishmen. Parliament's stance was that the Colonists were "virtually represented"- even though they didn't vote in elections, there were members of Parliament who sided with the Colonists (and it's true, particularly William Pitt the Elder), so it was OK that Colonists couldn't vote. The Colonists strongly disagreed.

Colonial resistance to the stamp tax resulted in economic troubles, which caused Parliament to repeal the Stamp Act only a few months after it was enacted. However, Parliament insisted that it had the right to tax the colonies, and other attempts to do so, particularly the Townshend Act and the Tea Act, would continue the path towards war and colonial independence.