With a lengthy paper trail of emails, the judicial misconduct case against popular and well-regarded Brooklyn Supreme Court Justice Barry Kamins will be difficult to defend, observers say, and may leave only the question of whether the judge’s foray into politics will end in a reprimand, his resignation or removal from office.

According to a report by the New York City Department of Investigation (DOI), Kamins may have violated the Code of Judicial Conduct—specifically the ban on direct or indirect political activity—by providing political and legal advice to an old friend, Charles “Joe” Hynes, as the longtime Brooklyn district attorney mounted a desperate and ultimately unsuccessful re-election battle last year.