Upon graduation, he joined the United States Navy, where he served as a radar officer on multiple ships, including the USS Sangamon, the victim of a kamikaze attack on May 24, 1945.

While Shadur left the courtroom on September 1, 2017, due to severe spinal stenosis, he never officially retired, handing off his final case shortly before his death.

In the first, he approved a consent decree ordering Cook County to improve conditions at their jail, calling for the release of prisoners to curtail severe overcrowding.

[5][6] Shadur was among the first federal judges to explicitly acknowledge abuse by Chicago police, using strong language to describe allegations of torture by officers in the 1990s.

"It is now common knowledge," Shadur wrote in 1999, "that in the early- to mid-1980s, Chicago Police Commander Jon Burge and many officers working under him regularly engaged in the physical abuse and torture of prisoners to extract confessions.

As his United States District Court colleague Robert Gettleman noted, "Long before pro bono representation was recognized as important by all segments of the bar, Milton Shadur lived his professional life as a lawyer faithful to the principle that one of the obligations of membership in the bar is the obligation to render uncompensated legal services to those unable to afford them.

"[6] Chicago Mayor Rahm Emanuel stated "Judge Milton Shadur devoted his life to upholding justice, to his country, and to his family.

He served the country bravely in uniform in World War II, honorably for 37 years on the bench, and will long be remembered for his sharp legal mind, independence and integrity.