Master Chief Calcaterra is a native of Missoula, Montana and attended Sentinel High School. Graduating high school in 1983, he joined the Navy in 1988. He completed Recruit Training and Basic Electricity and Electronics School in Great Lakes, Illinois. He attended Basic Submarine School at Groton, Connecticut in January 1989, followed by SONAR "A" School in San Diego, and SONAR "C" School in Kings Bay, Georgia.
Calcaterra's previous assignments include: USS Henry M. Jackson (SSBN 730), where he earned his Submarine Qualification Dolphins. USS Michigan (SSGN 727, Blue), Trident Training Facility Bangor, SSGN conversion on USS Michigan (SSGN 727), followed by a tour at Submarine Squadron 22 in La Maddalena, Italy, as the Squadron Sonarman, earning his Surface Warfare Qualification onboard USS Emory S. Land (AS-39).
Shore duty assignments include lead instructor at Trident Training Facility where he qualified Master Training Specialist. He is a graduate of the Senior Enlisted Academy, and the Chief of the Boat / Command Master Course. He was the Command Master Chief of Submarine Squadron 19 and Submarine Group 9 before assuming duties as Command Master Chief of Navy Region Northwest
In October 2007, Calcaterra relieved as the Chief of the Boat onboard USS Charlotte (SSN 766) helping the team earn a Meritorious Unit Commendation, 2009 Retention Honor Roll, Submarine Squadron 1 Tactical "T", Supply "E", and the Battle "E".
Calcaterra's personal decorations include the Meritorious Service Medal, Navy and Marine Corps Commendation Medal (two awards), the Navy and Marine Corps Achievement Medal (four awards), Good Conduct Medal (five awards), Global War on Terrorism Service Medal (one award), National Defense Service Medal (two awards), and Expert Pistol Marksmanship Medal.