The Court allowed him to file it in forma pauperis, which meant that the Court would waive the fees generally associated with such a petition. Generally, the Court dismisses most of these petitions; Gideon's was among those that it did not dismiss.
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Yes, of course it's legal to petition the US Supreme Court. When discussing Supreme Court cases, it's important to realize "petition" means to file an appeal of a case already decided by the lower courts. It does not mean to send a signature petition in protest or support of a decision. You are within your legal rights to send such a document, but the Court is not required to read it.
Gideon v. Wainwright (1963)
Gideon
US Supreme Court cases are initiated when a minimum of four justices agree to grant a petition for writ of certiorari.
Petition for a writ of certiorari For more information, see Related Questions, below.