Miami-Dade County Senior Judge Robert Deehl, who served on the bench for five decades and once sent Muhammad Ali to jail, has died just two days shy of his 88th birthday.

In a note announcing his death on Friday, Deehl's son David, a shareholder in the Miami firm Deehl & Carlson, said the judge died in Hendersonville, North Carolina, "surrounded by members of his loving family."