Jerry Saperstein (defendant) is the only shareholder of FontBank, Inc. (FontBank). Saperstein, acting pro se, sued CompuServe (plaintiff) in state court for breach of a contract with FontBank. Compuserve sued Saperstein and FontBank for tortious business practices and violations of Ohio law and sought a declaratory judgment in federal court. Saperstein counterclaimed for defamation, business torts, and business practice violations under Ohio and Illinois law. Saperstein’s claims were conclusory in nature, and CompuServe moved for a more definite statement on two of Saperstein’s four counterclaims. Saperstein filed an amended answer, adding names and a statement asserting that he had been unable to identify defamatory statements due to CompuServe’s failure to answer interrogatories and produce documents. Next, Saperstein refiled the amended answer with six additional counterclaims, though he did not request permission from the court under Federal Rule of Civil Procedure (FRCP) 15(a). The judge held a pretrial conference. Without giving Saperstein leave to amend, the judge granted CompuServe’s motion to strike Saperstein’s six new counterclaims and sua sponte dismissed all of Saperstein’s remaining claims without prejudice. The judge asserted that Saperstein had failed to provide a more definite statement despite amending his answer twice. CompuServe moved to dismiss its federal action without prejudice, which was denied. The court granted its subsequent motion to dismiss with prejudice. Saperstein appealed the dismissal of all claims.