Saylor was in private practice at
Goodwin Procter in
Boston, from 1981 to 1987, and from 1993 to 2004. He was an
assistant United States attorney in the U.S. Attorney's Office for the District of Massachusetts from 1987 to 1990. He later was a special counsel and chief of staff to
Robert Mueller, then assistant attorney general of the Criminal Division at the
United States Department of Justice, from 1990 to 1993. While at
Goodwin Procter, Saylor represented Circor International, Inc., KF Industries, Inc., and senior company officials as a criminal defense attorney while those companies were under investigation for smuggling Chinese-manufactured valves and selling the valves as a product of the U.S. between 2001 and 2004. The U.S. Attorney for the Southern District of Texas, Michael T. Shelby, dismissed the investigation days after Saylor was confirmed by the Senate.
Federal judicial service On July 30, 2003, Saylor was nominated by President
George W. Bush to a seat on the
United States District Court for the District of Massachusetts vacated by
Robert Keeton. Saylor was confirmed by the
United States Senate on June 1, 2004, and received his commission on June 2, 2004. He also served a term on the
United States Foreign Intelligence Surveillance Court from 2011 to 2018. Saylor became the chief judge on January 1, 2020, serving it until July 1, 2025. Saylor assumed
senior status on July 31, 2025. ==References==