Calabrese began his career as a student in the U.S. Air Force Academy, and was commissioned as a second lieutenant upon graduation in 1996. He completed intelligence training and became chief of intelligence for the 38th Reconnaissance Squadron and later the 4407th Reconnaissance Squadron. He later graduated from the Naval Postgraduate School and returned to the Air Force Academy to serve as a world history instructor.
Following the second inauguration of Donald Trump, substantial government and military resources were allocated to the US-Mexico border. In 2026, Calabrese became the first commanding general of the newly established Joint Interagency Task Force-Counter Cartel (JITF-CC).[3] In this role, he oversees a large interagency group with an anti-cartel focus.[4] Little is known about the group, and it maintains minimal public presence.
