Craig Osth was raised in Virginia's Shenandoah Valley. He was a dissertation short of a Ph.D. in Spanish and Latin American Literature from New York University's Madrid campus when he concluded that academic life was not for him. He entered CIA as a clandestine operations officer in early 1982, graduating with honors from the Agency’s training facility before beginning what would become an eleven-tour career spanning the early 1980s to the late 2010s. Near-native Spanish fluency took him first to Central America at the height of the Reagan Doctrine—as consequential a theater as any new officer could have hoped for. He went on to serve four successive tours as a unilateral case officer before transitioning to Station leadership. His seven Chief of Station assignments—in Latin America, Europe, South Asia, the Middle East, and domestically—are purportedly without precedent in the Agency's history. He worked operationally in four foreign languages and held the CIA equivalent of lieutenant general rank for the final dozen years of his career.