Tom Goldstein is slight, pale, and bald. Look in the dictionary, and next to the word “lawyer” you’ll find a picture of him. But in the legal circles of Washington, D.C., he is regarded with awe. That’s because Goldstein is one of the most successful Supreme Court advocates of the age.

Appearing just once in front of the Supreme Court of the United States—SCOTUS, for short—is, for most lawyers, the pinnacle of their career. Goldstein has done it 44 times, more than all but three lawyers in private practice in the Court’s modern history. His most recent case, Google v. Oracle, was described as the “copyright case of the century.”